Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.
This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

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Best Road Trips From Boston
For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.
Coastal Road Trip Destinations From Boston
1. Plymouth, MA
Distance From Boston: 40-50 minutes
If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.
Best things to do in Plymouth:
- Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
- Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
- Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
- Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
- Walk around the charming downtown to visit the shops and restaurants,
- Pop into Dirty Water Distillery for an artisanal spirits tasting.
- Go on a whale watch tour with Captain John’s Boat Tours.
- Spend the day getting pampered at Mirbeau Resort & Spa, and even stay for lunch or dinner, or the night for the ultimate day of relaxation.
Click here to book your stay at Mirbeau Resort & Spa!
Psst! I have an entire post on visiting Plymouth, MA, if you need more ideas!
2. Cape Cod, MA
Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.
Best Things To Do on Cape Cod:
- Visit The Cape Cod National Seashore
- Explore Chatham’s downtown
- Visit Provincetown and the Pilgrim Monument
- For more on the best things to do on the Cape, click the link below for my detailed travel guide.
You may also enjoy:
- Can’t Miss Things To Do When Visiting Cape Cod For The First Time
- Best Things To Do On Cape Cod For Adults
- Best Towns To Stay In On Cape Cod
- What To Pack For Cape Cod
- Unique Things To Do On Cape Cod
3. Nantucket, MA
Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.
To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.
Best Things To Do on Nantucket:
- Explore the shops and restaurants in the main town.
- Visit Brant Point Lighthouse.
- Rent a moped to explore the local beaches and towns.
- For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
You may also enjoy:
- The Best Nantucket Day Trip Travel Guide
- How Many Days Do You Need On Nantucket + Suggested Itineraries
- How To Visit All The Nantucket Lighthouses
4. Martha’s Vineyard, MA
Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.
To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).
Best Things To Do on Martha’s Vineyard:
- Gingerbread Cottages in Oak Bluffs
- Edgartown downtown and lighthouse
- Aquinnah Cliffs and Gay Head Lighthouse
- South/Katama Beach
- For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.
You may also find these Martha’s Vineyard posts helpful:
- Is Nantucket or Martha’s Vineyard Better For A Day Trip?
- The Ultimate Martha’s Vineyard Day Trip Guide
- How To See Martha’s Vineyard Without A Car
5. Marblehead, MA
Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.
Best Things To Do in Marblehead, MA:
- Marblehead Lighthouse & Chandler Hovey Park
- Self-guided historical home walking tour.
- Take in the views at Castle Hill Rock.
- For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.
Click here to read even more awesome things to do in Marblehead!
6. Salem, MA
Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.
Best Things To Do in Salem, MA:
- Winter Harbor Park and Lighthouse
- Salem Witch Trials Memorial
- Salem Maritimes National Historic Site
- Essex Street Pedestrian Mall
- House of Seven Gables
- Peabody Essex Museum
Psst! I have some helpful guides including planning the perfect Salem, MA day trip, and the best time to visit Salem if you need more information 😉
7. Rockport, MA
Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.
Best Things To Do in Rockport, MA:
- Visit Motif 1, the most painted building in New England, if not the country!
- Go for a scenic walk or hike at Halibut Point State Park.
- Meander through the shops on Bear Skin Neck.
- For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.
Click here for more amazing things to do in Rockport!
Click here to read my travel guide on the best things to do on Cape Ann!
8. Newburyport, MA
Distance From Boston: 40-50 minutes.

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.
Best Things To Do in Newburyport, MA:
- Visit Oldies Marketplace to look for antiques and treasures.
- Meander the streets of downtown to explore the beautiful storefronts.
- Take a leisurely stroll along the waterfront park.
- Pack a picnic or take a nature walk at Maudslay State Park, which has over 500 acres to explore.
- Head out on the open waters with Yankee Clipper Tours, and cruise around the Merrimack River and Newburyport Harbor.
- Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co., and walk the stunning nature trails at the Parker River National Wildlife Refugee.
Click here to read my full guide to visiting Newburyport & Plum Island!
9. Block Island, RI
Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.
Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.
It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.
To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here.
Best Things To Do on Block Island, RI:
- Take in the views at Mohegan Bluffs.
- Rent a moped to explore the entire island.
- Spend some time swimming at Mansion Beach.
- Visit the island’s two lighthouses.
- Have lunch with a water view at The Oar.
Click here to read all my tips for taking a Block Island day trip!
10. Newport, RI
Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.
With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.
Best Things To Do in Newport, RI:
- Walk along Cliff Walk for amazing coastal views.
- Visit Bowen’s Wharf for shopping and dining.
- Grab a lobster roll at the Newport Lobster Shack.
- Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
- Sail around Narrangansett Bay with Sightsailing of Newport.
- Visit the unique shops along Thames Street.
- Grab lunch and cocktails at The Lawn at Castle Hill Inn, overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!
Click here to book your stay at The Castle Hill Inn in Newport.
Click here to read all my tips for taking a Newport, RI day trip!
Click here to read about all the best things to do in Newport, RI in the winter!
11. Mystic, CT
Distance From Boston: 1.5 hours
This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.
Best Things To Do in Mystic, CT:
- See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium.
- Learn all about maritimes history at the Mystic Seaport Museum and Village, which is regarded as one of the best, if not the best, Maritimes museums in the country.
- Hit the trails at Bluff Point State Park.
- Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters.
- Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.
Click here to read about all the best things to do in Mystic, CT!
12. The Hamptons, NY
Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.
The Best Things To Do in The Hamptons:
- Have a beach day and watch the surfers at Coopers Beach in Southampton.
- Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
- Take in the views at Montauk Lighthouse.
- Enjoy an afternoon of rest and restoration at the Montauk Salt Caves.
- Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
- Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.
13. Ogunquit, ME
Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer, but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.
Best Things To Do in Ogunquit, ME:
- Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
- Visit Perkins Cove to enjoy its charming shops and restaurants.
- Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
- For more information on things to do in Ogunquit, click the link below for my detailed travel guide.
Click here to read about more amazing things to do in Ogunquit!
14. Kennebunkport, ME
Distance From Boston: 1 hour and 25 minutes
Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.
Best Things To Do in Kennebunkport, ME:
- Visit Gooch’s Beach for a walk along the shore, or go for a swim.
- Have an authentic lobsterman experience with Rugosa Lobster Tours.
- Walk around the downtown and Dock Square shops.
- Grab an artisanal ice cream cone at Rococo Ice Cream.
- Have some craft cocktails and beer at Batson River Brewing and Distillery.
- Walk along Parson’s Way for amazing views of the dramatic coastline.
- Grab fresh seafood takeout from The Clam Shack.
Click here to see why Kennebunkport is one of the best Christmas towns in New England!
15. Bar Harbor/Acadia National Park
Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.
Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.
Best Things To Do in Bar Harbor & Acadia National Park:
- Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
- Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
- Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
- Explore Bar Harbor’s downtown.
- Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
- Visit Bass Harbor Lighthouse inside Acadia.
Tip: You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here.
Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary, and the Best Time To Visit Acadia National Park.
Luxury Road Trip Destinations From Boston
These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.
16. Cliff House in Cape Neddick, ME
Distance From Boston: 1 hour and 15 minutes
If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.
What To Expect During Your Stay At Cliff House:
- Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
- Complimentary coffee, tea and water stations on each floor.
- A full-service spa.
- Three oceanfront restaurants and a coffee cafe.
- Manicured gardens and pathways for relaxing walks.
- Two outdoor pools, two indoor pools and a hot tub.
- On-site shopping.
Click here to book your stay at Cliff House!
17. Ocean House in Westerly, RI
Distance From Boston: 1 hour and 45 minutes
For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.
What To Expect During Your Stay At Ocean House:
- Freshly designed and elegant coastal New England rooms and suites.
- Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
- Complimentary activities within the resort, such as daily yoga and cooking classes.
- Valet parking included in your room rate.
- Four on-site restaurants, and lobster dinners on the lawn during the summer.
- An on-site spa.
- Beautifully manicured lawns with yard games.
- Complimentary refreshments throughout the day.
Click here to book your stay at the Ocean House!
18. Mohonk Mountain House in New Paltz, NY
Distance From Boston: 3 hours and 45 minutes
If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.
Overviews of the resort have been used in the Amazon Prime series Upload, and has long been rumored to be the inspiration behind Stephen King’s The Shining. But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.
If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.
What To Expect During Your Stay At Mohonk Mountain House:
- Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
- Lake Mohonk on the resort grounds.
- An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
- 85 miles of hiking trails right outside your door.
- Farm-to-table dining.
- An on-site spa.
- Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.
Click here to book your stay at Mohonk Mountain House!
Click here to read my detailed review of a Mohonk Mountain House Day Pass!
19. Mirbeau Spa in Rhinebeck, NY
Distance From Boston: 3 hours and 10 minutes
Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.
The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.
What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:
- A serene, calm spa atmosphere throughout the entire grounds.
- A relaxation room, aqua terrace and steam facility within the spa.
- Different spa packages to customize your stay that include dining options to make your visit stress-free.
- Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.
Click here to book your stay at Mirbeau in Rhinbeck!
Charming Small Town Road Trip Destinations From Boston
If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.
20. Saratoga Springs, NY
Distance From Boston: 3 hours and 15 minutes
While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.
Best Things To Do in Saratoga Springs, NY:
- Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
- July – Labor Day, visit the Race Track, and even try your hand at placing bets on the winner!
- Stroll through Congress Park, and find the mineral springs to taste the local water.
- Enjoy a healing bath at the Roosevelt Baths & Spa. The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
- Take in a live show at SPAC, one of the the country’s most renowned outdoor concert venues.
- Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
- Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.
Click here to book your stay at the Adelphi Hotel in Saratoga Springs!
21. Skaneateles, NY
Distance From Boston: 5 hours and 20 minutes
Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.
Best Things To Do in Skaneateles, NY:
- Walk around Main Street to visit the boutiques.
- Sit and admire the views of the lake from the town’s many waterfront areas.
- Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
- Head out onto the lake for a boat tour.
- Grab dinner and drinks at the Sherwood Inn, located right in the heart of town, and just across the street from the lake.
- Spend the day getting pampered at Mirbeau Inn & Spa, the original Mirbeau location, which is home to a Monet-inspired garden and bridge.
Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!
Click here to read more suggestions on the best things to do in Skaneateles, NY!
22. Lake Placid, NY
Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.
Best Things To Do in Lake Placid, NY:
- Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
- In the winter, enjoy skiing at Whiteface Mountain, and ice skating and a Toboggan Chute on Mirror Lake.
- Enjoy the miles of hiking trails in the nearby mountains.
- Walk around the alpine-inspired downtown village to visit the quaint shops.
- In the summer, go for a swim in Mirror Lake from the public beach area.
- Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum.
- Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
- Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!
Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid.
Click here to read my post on all the best things to do in Lake Placid in the fall!
23. Hudson, NY
Distance From Boston: 2 hours and 45 minutes
Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.
Best Things To Do in Hudson, NY:
- Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse, which has over 300,000 sq. feet of treasures.
- Stroll down Warren Street, where most of the storefronts can be found.
- Take a boat cruise along the Hudson River with Hudson Cruises, which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
- The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
- Tour the local art galleries.
- Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.
Click here to read my post on the best things to do in Upstate New York in the fall!
24. Manchester, VT
Distance From Boston: 3 hours and 10 minutes
This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.
Best Things To Do in Manchester, VT:
- Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
- Browse through Northshire Bookstore, an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
- Visit Hildene, the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
- Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
- Grab a sandwich as big as your head at Zoey’s Deli. I also love their homemade chips!
- Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
- Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
- After your swim, visit the Dorset Union Store, a quintessential Vermont country store.
Click here for an awesome Vermont covered bridges tour itinerary!
25. Woodstock, VT
Distance From Boston: 2.5 hours
Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.
Best Things To Do in Woodstock, VT:
- Walk through the truly adorable village and enjoy the local shops and coffee cafes.
- Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
- Get your hands muddy with a pottery workshop at Farmhouse Pottery.
- Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill, and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
- Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
- Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
- Hike Mount Tom for stunning views of Woodstock from above.
You may also enjoy:
- Best Places To Stay In Vermont In The Fall
- Best Things To Do In Woodstock, VT
- Best Winter Getaways In New England
26. Stowe, VT
Distance From Boston: 3 hours and 20 minutes
Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.
Best Things To Do in Stowe, VT:
- Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
- See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
- Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
- Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
- Go hiking at Smuggler’s Notch State Park.
- Visit the nearby Ben & Jerry’s Factory for a tour.
- Explore Sterling Falls Gorge.
- In the winter, hit the slopes at Stowe Mountain Ski Resort.
- Pick up some chocolates from Lake Champlain Chocolates.
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27. Greenwich, CT
Distance From Boston: 3 hours
Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.
Best Things To Do in Greenwich, CT:
- Shop the stores along Greenwich Avenue.
- Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
- Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
- Head to the Lobster Bin for an amazing lobster roll on-the-go.
- Spend some time at the beaches along Greenwich Point Park.
- Admire the architecture of the historic district buildings.
28. Jackson, NH
Distance From Boston: 2 hours and 45 minutes
Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.
Best Things To Do in Jackson, NH:
- Visit Honeymoon Bridge, the town’s famous red covered bridge.
- Drive to the summit of Mount Washington, the highest peak in New England.
- Hike the Glen Ellis Falls Trail.
- Explore the downtown shops and restaurants.
- In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.
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City Life Road Trip Destinations From Boston
Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.
29. Portsmouth, NH
Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.
Best Things To Do in Portsmouth, NH:
- Grab some fresh and delicious pastries from Elephantine Bakery, and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
- Shop the boutiques in downtown Portsmouth.
- Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
- Take a dip in the water at Great Island Common Park.
- Go brewery hopping, as Portsmouth is home to five breweries.
- Enjoy a drink at the Book & Bar, a combined bookstore, cafe and bar.
- Head out onto the water with Portsmouth Harbor Cruises.
- Visit Portsmouth Harbor Lighthouse.
30. Providence, RI
Distance From Boston: 1 hour

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.
Best Things To Do in Providence, RI:
- Visit The Arcade, the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
- Visit the Roger Williams Park Zoo, which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
- Enjoy a leisurely walk along the Providence Riverwalk.
- During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
- Take in the exhibits at the RISD Museum of Art.
- Take a Venetian gondola ride along the river at Waterplace Park.
- Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
- Take a boat tour along the Providence River.
Click here to read my post on the best day trips from Providence!
31. Portland, ME
Distance From Boston: 1 hour and 45 minutes

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.
Best Things To Do in Portland, ME:
- Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
- Visit one of my favorite breweries in New England, Bissell Brothers. They also get bonus points for being close to the waterfront at Thompson’s Point.
- Meander around Old Port to see the city’s fishing industry come to life.
- Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
- Tour the open waters on a beautiful Schooner tour with Portland Schooner. They also invite you to pack a picnic with beer and wine to enhance your experience.
- Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
- Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.
Click here to book your walking culinary tour in Portland!
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32. New York City
Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.
The Best Things To Do in New York City:
- Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
- Get bagels at Brooklyn Bagel (the best in the city).
- Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
- Grab a slice of pizza at Joe’s (150 E 14th St.)
- Explore the MET Museum and Cloisters.
- Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
- See a broadway show.
- It’s touristy, but I love going to the top of the Empire State Building.
- Walk around the West Village for amazing streets and brownstones.
33. Burlington, VT
Distance From Boston: 2.5 hours

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.
Best Things To Do in Burlington, VT:
- Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
- Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
- Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
- Go kayaking or stand up paddleboarding on the lake.
- Head to nearby Shelburne to tour Shelburne Farms, one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
- Take in the art scene on the South End, which is loaded with galleries and shops.
- Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.
Click here to book your Beer of Burlington experience!
34. Philadelphia, PA
Distance From Boston: 5 hours

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.
Best Things To Do in Philadelphia, PA:
- Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
- Speaking of the Philadelphia Museum of Art, after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
- Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
- Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
- Grab a Philly cheesesteak at Woodrow’s Sandwich Shop.
- Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
- Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.
Click here to book your Historically Hilarious Trolley Tour in Philadelphia!
Road Trip Itinerary Options
If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.
Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:
- Marblehead
- Salem
- Rockport
- Newburyport & Plum Island
- Portsmouth, NH
Days Needed For This Route: 2-4. If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.
Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:
- Plymouth
- Cape Cod
- Nantucket
- Martha’s Vineyard
Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.
If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days. If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.
Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:
- Newburyport, MA
- Ogunquit, ME
- Kennebunkport, ME
- Portland, ME
- Bar Harbor, ME
Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.
If you’re very short on time, you can do this route in 4 nights with this itinerary:
- On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
- The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
- The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
- Drive back to Boston.
I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!
Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:
- Manchester, VT
- Woodstock, VT
- Stowe, VT
- Burlington, VT
Note: This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.
Days Needed For This Route: 3-5 days. This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.
Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:
- Providence, RI
- Newport, RI
- Block Island, RI
- Westerly, RI
- Mystic, CT
Days Needed For This Route: 3-6 days. This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.
Tip: If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!
Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:
- Hudson, NY
- Rhinebeck, NY
- New Paltz, NY
- New York City
- The Hamptons
- Optional add-on: Philadelphia, PA
Note: The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.
Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.
If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.
The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.
What Towns Are 1 Hour From Boston?
Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.
Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.
What Cities Are 6 Hours From Boston?
New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.
Is Boston Close To Niagara Falls?
Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.
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That’s A Wrap On The Best Road Trips From Boston
As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.