Between gorgeous, historic cities to some of the most stunning coastline the U.S. has to offer, New England offers an incredible variety of day trip destinations for pretty much anyone. Whether you’re looking to tackle some epic hikes in the mountains, spend the day by the beach, get lost on cobblestone streets or spend your day eating all the amazing food, I’ve got you covered with my suggestions on the absolute best day trips in New England!
Hi there, and welcome! I’ve been exploring the New England region for over 15 years now, and I also live locally in the northeast. My favorite thing in the world is to explore this corner of the U.S., and I’ve covered a lot of ground over the years. I truly believe that all of the places I’ve included on this list are worth your time, and are easy to navigate with just one day.
I’ve also grouped each destination by season, but it’s good to know that pretty much all of these suggestions are wonderful year-round. In fact, it was really hard to group some of them into a specific season because many of them offers incredible things to do year-round. So, while I’ve made some seasonal suggestions, keep in mind that most places are truly perfect throughout the entire year.
Are you ready? Let’s get started!
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Best Day Trips In New England In The Summer
1. Provincetown, MA
Best as a day trip from: Boston, Plymouth, other towns on Cape Cod, Massachusetts North & South Shore.
One of the most unique towns in the entire U.S. is Provincetown, and because it’s small and easily walkable, it makes for a perfect day trip in New England.
Provincetown is an especially easy day trip for those coming from Boston and Plymouth, as there are ferries that will take you right to MacMillan Pier in downtown Provincetown. Both ferry options only take 90 minutes, making them very convenient options.
🛳 Click here to check out the ferry from Boston to Provincetown!
🛳 Click here to checkout the ferry from Plymouth to Provincetown!
During the summer season, a free shuttle takes visitors from MacMillan Pier to Race Point and Herring Cove beaches, which are two of the most beautiful beaches on Cape Cod. And once you’re in Ptown (as the locals call it!), you can easily walk everywhere.
Top things to check out in Provincetown:
- The Cape Cod National Seashore
- Commercial Street
- Lobster Pot restaurant
- Pilgrim Monument
- The real pilgrim landing site
- Beautiful art galleries
→ Click here to read my full guide on even more awesome things to do in Provincetown!
2. Nantucket, MA
Best as a day trip from: Cape Cod
One of the best day trips from Cape Cod is Nantucket Island, and I also think it’s one of the best places to see in all of New England. Filled with picturesque coastal scenery around every turn, I always describe Nantucket as both modern and stuck in time. Between the historic homes and cobblestone streets, breathtaking beaches and the most charming downtown boutiques, it’s the perfect way to spend a day when in the area.
→ Click here to read my guide on everything you need to know about a Nantucket day trip!
3. Martha’s Vineyard
Best as a day trip from: Cape Cod, Boston, New Bedford
Martha’s Vineyard is the other Cape Cod island that’s popular for summer vacations and day trips, and for good reason! It’s a bit bigger than Nantucket, but the ferry ride over from Cape Cod is shorter. And with 6 gorgeous towns to explore, there’s no shortage of ways to have fun on a day trip.
While there is no direct ferry from Boston to Martha’s Vineyard, there is a day tour that you can book that will take care of all the transportation for you! This is a great way to plan a summer escape from the city without having to drive yourself.
🚐 Click here to book your Boston to Martha’s Vineyard tour!
Here are some other Martha’s Vineyard posts you may find helpful:
- The Ultimate Guide To A Martha’s Vineyard Day Trip!
- Is Martha’s Vineyard or Nantucket Better For A Day Trip?
- How To See Martha’s Vineyard Without A Car
- Best Things To Do On Martha’s Vineyard
4. Block Island, RI
Best as a day trip from: Newport, Boston, Providence and surrounding Rhode Island areas
As much as I love Cape Cod and the Islands, I think Block Island is such a special place and deserves more hype. This little island sits off the coast of Point Judith, RI, and is a short 30-60 minute ferry from there, making this a very easy day trip from the Ocean State!
And one of the amazing things about this little island is that all the beaches are completely free for all visitors, which is a rare thing in New England. In addition to that, there are some really wonderful restaurants, a cute downtown and some gorgeous sites to see.
→ Click here to read my full guide on taking a Block Island day trip!
5. Newport, RI
Best as a day trip from: Boston, Providence and surrounding areas
Nicknamed The City By The Sea, Newport feels more like a charming coastal town than a vibrant city. Packed with history, stunning Gilded Age mansions, character, beautiful coastline views, beaches, and an exciting culinary scene, there are so many fun things to do there that make for a perfect day trip in New England.
The biggest tip I have for you about Newport in the summer is that it can get busy, which means parking can sometimes be challenging. I highly recommend that you park and leave your car for the entire day, rather than trying to drive everywhere. Newport is pretty walkable, but a great option is taking a trolley tour so you can see the major sites in a short amount of time.
This particular tour also includes admission to The Breakers Mansion,
which is one of the top things to see in Newport:
→ Click here to check out the trolley & Breakers Mansion tour in Newport
Newport also offers amazing tours out on the water!
A great way to end your day trip is with a sunset cruise, and this is an awesome one to consider:
→ Click here to check out this sunset cruise in Newport!
→ Click here to read my full guide on a Newport day trip!
6. Westerly, RI
Best as a day trip from: Newport, Boston, Providence and surrounding areas
Westerly is one of the best beach towns in Rhode Island for a summer vacation or day trip! With miles of gorgeous shoreline to explore across several stunning beaches, this is the perfect place to spend a hot summer day.
And not only are the beaches absolutely beautiful, there’s also a charming downtown with awesome restaurants and shops to explore. Westerly is also home to the charming village of Watch Hill, which is where you’ll find a lighthouse, the iconic Ocean House resort, Napatree Point (pictured above!) and lots of beautiful scenery.
Here are some other great things to check out in Westerly:
- Misquamicut State Beach – the best public beach in town!
- Tapped Apple Cidery & Winery
- Grey Sail Brewing
- Sailing tour with Sail Trim Again
Tips for visiting Watch Hill in Westerly: Parking here in tough during high season (summer) and on weekends. The free parking spots are limited to 2 hours, so if you plan to dine anywhere, or spend time at the beaches, you’ll want to arrange for paid parking in one of the lots. Parking around the rest of Westerly isn’t as big of an issue.
→ Click here to read my full guide on the best things to do in Westerly, RI & Watch Hill!
7. Kennebunkport, ME
Best as a day trip from: Portland, Massachusetts North Shore, Boston
Honestly, Kennebunkport is an amazing coastal destination year-round because they really know how to celebrate what’s special about each season. In fact, their Christmas events have put this cute little community on the map as one of the best Christmas towns in the U.S.! But the summer is definitely one of the most popular season to experience Kennebunkport.
This town really has it all – lovely stores and restaurants, a quaint downtown, New England charm, dramatic coastline and gorgeous beaches. Here are a few wonderful things to do on a Kennebunkport day trip:
- Walk Parson’s Way for amazing coastal views (and see the famous Bush compound!)
- Walk through the shops at Dock Square.
- Visit the beaches (Gooch’s, Mother’s and Goose Rocks).
- Get a lobster roll from The Clam Shack.
- Take a lobster boat tour with Rugosa.
8. Ogunquit, ME
Best as a day trip from: Portland, Massachusetts North Shore, Boston
Another charming town that’s perfect for enjoying a summer day in Maine is Ogunquit. This destination is home to one of the best beaches in Maine – Ogunquit Beach, which has 3 miles of beautiful, soft, sandy shoreline to enjoy.
In addition to the beach, you’ll find an incredibly charming town with great shops and restaurants, and one of my absolute favorite things to do in all of Maine – Marginal Way, which is a gorgeous pedestrian path along the coastline.
→ Click here to read my full guide on the best things to do in Ogunquit!
9. Boothbay Harbor, ME
Best as a day trip from: Portland and surrounding areas.
Located between Portland and Acadia National Park, you’ll find the adorable town of Boothbay Harbor. While this destination is great during spring, summer and fall, summer is one of the best times to visit because all the seasonal restaurants and boat tours will be open, allowing you to get the full experience during your trip.
One of the reasons I love Boothbay Harbor so much is because of all the amazing options available for boat tours. Boats here go a bit further north than tours that depart from Portland, so you’ll get to see some more remote parts of the coastline, lighthouses and incredible wildlife. They even offer tours to see a puffin colony!
One of the coolest tours to take during a day trip is the Seals, Lighthouses & Lobster Trap tour, which offers so many great things to see in just 1.5 hours. During the cruise, you’re also likely to spot some seals in the water, and watch a real lobster trap haul.
→ Click here to check rates & availability for the Seals, Lighthouses & Lobster Trap Tour
Psst! I have a detailed guide on the best things to do in Boothbay Harbor, if you need more ideas for your day trip 😉
10. Lubec, ME
Best as a day trip from: Bar Harbor, Bangor
Okay, so Lubec is a bit more challenging as a day trip because it’s so remote, and pretty close to the Canadian border, but I wanted to include it on this list for anyone looking for an amazing day trip option that’s a bit of a hidden gem.
Lubec offers absolutely stunning opportunities for hiking and coastline views, and is also home to the famous red and white striped lighthouse, West Quoddy Light. I also love that it’s a quaint and quiet little fishing village that not many people visit. The actual village itself doesn’t have a ton to do, but I think the landscapes and hiking here are more than worth the effort to visit.
A few things that are a must for a day trip:
- Explore West Quoddy State Park to see the lighthouse and do some of the walking trails.
- Hike the Boot Head Preserve trail.
- Taste the local beer at Lubec Brewing Company.
- Take a boat tour to Old Sow Whirlpool.
→ Click here to read my full guide on even more things to do in Lubec!
11. Mystic, CT
Best as a day trip from: Boston, Newport, Providence
One of the most charming towns along the Connecticut coast is Mystic, made famous, of course, by the movie Mystic Pizza. Mystic makes for a wonderful day trip in the area because it’s small and walkable, offers boat tours along the river and is close to the Connecticut Wine Trail, which is incredibly fun and scenic!
One of the top things to do in Mystic is the Mystic Seaport Museum, which is a highly interactive museum that’s built to replicate a historic New England ship yard and town. You can climb aboard historic tall ships and admire the views of the river while learning about its incredible history. This is actually a really fun way to spend a few hours in Mystic (and I’m not usually a museum person!).
→ Click here to get your ticket to the Mystic Seaport Museum
Psst! I have an entire guide on the best things to do in Mystic, CT if you’re looking for more ideas 😉
12. Manchester, VT
Best as a day trip from: The Berkshires, Northwestern Massachusetts, surrounding areas in Vermont
While Vermont is known as a top fall and winter destination in New England, I especially love to visit Manchester in the summer. Located in southern Vermont, this cute little town is home to some really fun ways to cool down on hot summer days, including swimming in a rock quarry and floating down a river in an inner tube.
The Dorset Marble Quarry is just a few minutes from downtown Manchester, and is a really cool and unique place to go for a swim. And with Vermont River Runners, you can rent an inner tube and float down the Battenkill River. They’ll even pick you up at the end do you don’t have to worry about getting back to your car!
Once you’re done splashing in the water, you can also explore the cute little downtown, which has some lovely shops and eateries, and maybe even visit Hildene, which is a former Lincoln family home, and boasts stunning garden displays and mountain views.
13. Shelburne Falls, MA
Best as a day trip from: The Berkshires, Northwestern Massachusetts, surrounding areas in Vermont
This small little town nestled in The Berkshires has been made famous by its No. 1 attraction – the Bridge of Flowers. And honestly? It’s worth the type.
Once an old trolley bridge that became obsolete is now a beautiful and cheerful display of colorful flowers from spring to fall. But in the summer, you’ll find the most blooms to enjoy during your visit.
Shelbune Falls also has a Trolley Museum, brewery and one of the oldest bowling alleys in the country, so you’ll definitely be able to fill your day trip with cool things to do.
14. Gloucester, MA
Best as a day trip from: Boston, Portland, Massachusetts North Shore, Plymouth
Gloucester is another destination that’s really great to visit in spring, summer and fall, but since it’s home to one of the best beaches along the North Shore, it makes for an especially wonderful day trip in New England in the summer months.
Wingaersheek Beach is a beautiful spot for swimming, and makes for an awesome escape from city life in Boston and Portland. You can easily spend your entire day just at the beach, as it has a snack shack, and provides a beautiful sunset.
Gloucester is also one of the best locations in the Northeast for whale watching! Tours from Gloucester cruise to the Stellwagen Bank National Marine Sanctuary, which is regarded as the best spot in New England for spotting wildlife.
→ Click here to book your whale watch in Gloucester!
Gloucester is also home to a beautiful lighthouse, wonderful downtown with shops and amazing restaurants, and a waterfront park to explore.
Best New England Day Trips In The Fall
15. Bar Harbor/Acadia National Park
Best as a day trip from: Portland, Bangor
While Acadia National Park and Bar Harbor can be challenging to do as a day trip because of their location, it’s absolutely worth the effort! Acadia National Park, especially, is one of the best things to see in all of New England, so even a day spent here is better than not seeing it at all. And during the fall season, you’ll experience better temperatures for hiking, as well as stunning fall foliage.
But honestly, spring and summer are equally as great, so it’s really personal preference on when you plan your day trip!
Psst! I have a full Acadia National Park itinerary, which includes a bonus day trip itinerary option, and a guide on the best time to visit Acadia National Park, which you may find helpful 😉
16. Springfield, MA For The Big E Fair
Best as a day trip from: Boston, Providence, Newport, Mystic
One of the best days trips to take to celebrate the end of summer and beginning of fall is Springfield, so you can attend The Big E, which is the biggest fair in New England!
All 6 of the New England states take part in this fair, and between the awesome fair and regional foods, rides, shopping, exhibitions, live performances and so much more, it really is the quintessential fair experience. Many people come from all over the region to attend, so you know it must be good.
17. Salem, MA
Best as a day trip from: Boston, Massachusetts North & South Shore, Providence, Plymouth
Salem is regarded as one of the top Halloween destinations in the entire world, so it rarely needs an introduction. But I can honestly say that it really is such a fun place to experience during the month of October. And because it’s smaller than most people realize, it’s actually very easy to explore in a day.
Since Salem is about all things spooky, I highly suggest getting into the spirit and doing a spooky tour of some sort. There are so many tours offered in Salem that talk about everything from the fascinating history, to Hocus Pocus filing locations to all the very creepy ghost sightings.
A great tour that’s perfect for most people is this History & Hauntings Tour, which talks about the history with a few spooky facts thrown in for good measure:
→ Click here to book the History & Hauntings Tour in Salem!
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 😉
18. Plymouth, MA
Best as a day trip from: Cape Cod, Boston, Massachusetts South & North Shore, Providence, Newport
Plymouth is one of the oldest towns in the entire U.S., so of course, it’s absolutely worth a day trip if in the area! And while it’s known for its history, it’s also home to some beautiful parks and a cute downtown.
The reason I love Plymouth for a day trip in the fall is because there’s something about this area that reminds me so much of “back to school,” and it also does a fantastic job celebrating the Thanksgiving holiday, of course! It’s also one of the last parts of New England to hit peak fall foliage, so if you’re looking for a foliage destination in early November, Plymouth is perfect for that timeframe!
However, Plymouth is, of course, wonderful year-round, too 😊
The top attraction in Plymouth is the Plimoth Patuxet Museum, which immerses visitors
into the life of the early settlers. You can even climb aboard the Mayflower II, which is a
working replica of the original Mayflower!
→ Click here to get your tickets to the Plimoth Patuxet Museums!
In addition to the museums, some other great things to check out in Plymouth are:
- Mirbeau Spa
- The shops and eateries downtown
- Brewster Gardens
- Pilgrim Memorial State Park
- Plymouth Bay Winery
- Plymouth Long Beach
Psst! I have an entire post on visiting Plymouth, MA, if you need more ideas for your day trip!
19. Marblehead, MA
Best as a day trip from: Boston, Massachusetts North & South Shore, Providence, Plymouth
Along the Massachusetts North Shore is the beautiful town of Marblehead, which is really great to visit in both summer and fall. But fall is an especially beautiful time to visit because of the stunning foliage displays, of course.
While walking around to enjoy the foliage, you’ll also want to be sure to visit the charming shops in the historic district, enjoy the coastal views from Castle Rock Park, take a walk on Devereux Beach and admire the gorgeous, historic New England homes.
→ Click here to read my full guide on the best things to do in Marblehead!
20. Newburyport, MA
Best as a day trip from: Boston, Portland, Massachusetts North & South Shore
Newburyport is another destination that’s truly wonderful year-round, but I especially love it in the fall because of all the fall color. This is also one of my top places to visit for shopping, and even Boston Magazine named Tannery Marketplace in Newburyport one of the best places for shopping on the North Shore.
Newburyport is also pretty small, and the downtown area is very walkable, making this a perfect day trip option. It’s also home to Plum Island, which has beautiful beaches, as well as the Parker River National Wildlife Refuge, which has gorgeous nature trails to explore.
Here are a few awesome things to do on a Newburyport day trip:
- Stroll along the waterfront park.
- Explore all the amazing shops in Market Square and Tannery Marketplace.
- Visit Maudslay State Park.
- Drive to Plum Island to see the beaches, and hit the scenic trails in the Parker River National Wildlife Refuge.
→ Click here to read my full guide on visiting Newburyport!
21. The Berkshires
Best as a day trip from: Northwestern Massachusetts, surrounding Vermont areas
During the fall season, The Berkshires puts on a beautiful foliage display, and this is one of the most cozy places to be this time of the year. Between all the amazing hiking opportunities, quaint towns and gorgeous mountain landscapes, it also makes for a fun and adventurous day trip in Massachusetts.
The Berkshires is actually made up of 31 towns and 2 cities, so it’s a pretty big area to tackle in a day trip, but that just means you have a lot of exciting activities to choose from. Here are a few awesome things to consider for a fall day trip to The Berkshires:
- Go seasonal beer and hard cider tasting (there are tons of options!).
- Admire the foliage during a ziplining tour with Berkshire East Mountain Resort.
- Drive or hike to the summit of Mount Greylock for amazing fall foliage views.
- Pick apples, hike and sample the local wine at Hilltop Orchards.
22. Woodstock, VT
Best as a day trip from: Surrounding Vermont areas, White Mountains
One of the top fall foliage destinations in the entire U.S. is Vermont, and Woodstock is one of the most charming and picturesque towns to experience. In Woodstock, not only will you get the enjoy some of the best fall foliage in Vermont, you’ll feel as though you’ve stepped into a Hallmark movie set when you arrive to the cute little town.
Woodstock’s village is about as perfect as can be with beautiful boutiques and quaint restaurants. In the center of town, there’s even a covered bridge!
But just outside of the village, you’ll find Billings Farm & Museum, which is regarded as one of the best interactive agricultural museums in the country. You can also visit Sugarbush Farms to sample their own maple syrups and cheeses, and enjoy stunning mountain views dripping in fall color.
→ Click here to read my full guide on the best things to do in Woodstock!
23. Burlington, VT
Best as a day trip from: Surrounding Vermont areas, White Mountains
Another wonderful day trip in Vermont in the fall season is Burlington. As the largest city in the state, it has a lot to offer including the beautiful Lake Champlain, amazing restaurants, art galleries, breweries and so much more.
In fact, one of the most fun things to do in Burlington on a day trip is dive into the local brewing scene with a tour!
Vermont produces some of the top beers in the country, and this tour is led by a local expert that gives you all the insider tips, and allows you to sample up to 12 different beers. This time of the year, there are likely to be seasonal beers available, too.
→ Click here to book your brewery tour in Burlington!
You’ll also want to be sure to walk the waterfront path along Lake Champlain for beautiful fall foliage views, and hit up Church Street Marketplace to enjoy the local shops.
24. Littleton, NH
Best as a day trip from: Vermont, surrounding New Hampshire areas
One of my personal favorite towns in the White Mountains region of New Hampshire is Littleton. Not only has it been named of the best Main Streets in the entire country, it’s home to a charming little community with awesome shops, restaurants, a brewery, and the world’s largest candy counter (it’s true!).
And since it’s only about 20 minutes from some of the top fall foliage sites in Franconia Notch State Park (like Flume Gorge and Echo Lake), this is the perfect day trip to take while exploring the area.
→ Click here to read my full guide on all the best things to do in Littleton.
25. Montpelier, VT
Best as a day trip from: Surrounding Vermont areas, White Mountains
Montpelier is Vermont’s capital, and I think it’s a very underrated destination in the area. The cool thing about Montpelier is that it’s a city that feels like both a city and a quaint town at the same time, so exploring for the day is very easy to do. And during the fall season, there are a lot of fun seasonal activities you can enjoy.
Here are a few things you should look into for a Montpelier day trip in the fall:
- The annual Enchanted Forest Celebration in October.
- Visit Peck Farm Orchard to pick apples, get some cider donuts and sample their hard cider.
- Stroll through town to visit the boutiques and eateries.
- Head to Hubbard Park to enjoy the fall foliage.
- Drive to nearby Groton State Forest to tackle some fall foliage hikes.
26. Litchfield Hills, CT
Best as a day trip from: Mystic, The Berkshires, New Haven, Hartford
Fun fact: Amy Sherman Palladino based Stars Hollow on a few towns in the Litchfield Hills area of Connecticut, so this is one of the best New England day trips for Gilmore Girls fans. It’s said that Washington Depot was her main inspiration, but many have claimed that New Milford’s town green feels most like a Stars Hollow set.
But even if you know nothing about Gilmore Girls, this is an incredibly stunning area to visit for a day trip, especially in the fall. You’ll find covered bridges, scenic drives, cozy restaurants, quaint towns and state parks that will be ablaze with foliage color this time of the year. And since all the small towns are pretty close to one another, you can easily see most of them in one day trip.
The towns in Litchfield county also have tons of fun fall festivals and events that take place through September and October, and those are worth checking out.
Here are some awesome ideas for the perfect fall day trip to the Litchfield Hills:
- Explore the charming town of Kent, including Bull’s Covered Bridge and Kent Falls State Park.
- Drive the scenic Route 7 to New Milford to enjoy the town green, and take in foliage views from Lovers Leap State Park.
- Enjoy the picturesque town of Washington Depot, and sample the local wines at Hopkins Vineyard.
- Drive to Litchfield and enjoy getting lost in the Bunnell Farm corn maze, and explore the cute town.
Psst! If you’re a Gilmore Girls fan, you may want to check out my post on Where To Find The Real Stars Hollow 😉
Best New England Day Trips In The Winter
27. Stowe, VT
Best as a day trip from: Surrounding Vermont areas, White Mountains
Stowe is hard to beat as a charming, small town winter day trip in Vermont. It’s also one of the best places in Vermont in the fall season, but I decided to add it to the winter section because it has a little something extra in the winter that just feels magical.
In January, you can visit during their winter carnival to see professional ice sculptors in action. And you can also plan a visit to the Spruce Peak Lodge resort to skate at their scenic ice rink, and enjoy lunch at one of their restaurants.
And, of course, you can’t talk about Stowe without mentioning the ski resort, which is continually voted as one of the best in the region. If you love to hit the slopes in the winter, this is one of the best day trips you can take in New England!
→ Click here to read my full guide on all the best things to do in Stowe!
28. Camden, ME
Best as a day trip from: Portland, Bar Harbor, surrounding areas in Maine
Camden is honestly awesome year-round, especially in the summer for windjammer cruises around the harbor, and in the fall season for colorful foliage. But in winter, it’s home to one of the most exciting winter parks in Maine – the Camden Snow Bowl.
The Camden Snow Bowl offers ski trails, a snow tubing park, and even a very fun toboggan chute. In February, the famous toboggan chute is actually the location of the U.S. Toboggan Championships. But if you visit outside of the competition weekend, visitors are able to fly down the chute during their visit (which I highly recommend).
Camden is also often named one of Maine’s most beautiful towns, so during your day trip, you should also plan to visit the charming Main Street downtown, which is home to cute shops and restaurants.
29. Lincoln, NH
Best as a day trip from: Surrounding areas in the White Mountains and Vermont, Portsmouth
If you’re nearby Lincoln, NH in the winter season, you’ll want to consider a day trip to see the famous Ice Castles, which only puts on a few displays throughout the U.S. Technically located in South Woodstock (which is only a few minutes from Lincoln), the Ice Castles display is really something special to see with your own eyes.
Not only is there a giant castle carved out of ice (that changes each year!), there are also often special features like ice slides, sleigh rides, tunnels, tubing and more.
And because there are so many other winter activities in Lincoln like skiing and scenic gondola rides at Loon Mountain, ice skating at RiverWalk resort, sleigh rides at Franconia Notch stables, there are tons of ways to fill up your day trip itinerary.
→ Click here to read my guide on all the best things to do in Lincoln!
30. Jackson, NH
Best as a day trip from: Surrounding areas in the White Mountains and Vermont, Portsmouth
Jackson is another amazing winter destination for a day trip in the White Mountains region of New Hampshire. And since it’s only just an over an hour from Lincoln, you could easily combine the two for a winter wonderland day of fun.
One of the best things to do in the winter is actually drive from Lincoln (the previous suggestion!) to Jackson for a scenic winter drive. You have two options for this, both of which are beautiful: The Kancamagus Highway, and the drive through Crawford Notch State Park (along Route 302). Both will take about the same amount of time, so it’s really personal preference.
Once you arrive in Jackson, there are tons of downhill, cross-country ski and snowshoe trails to explore.
Another wonderful winter activity in Jackson is Nestlenook Farms, which has one of the most beautiful outdoor ice skating rinks, and they also offer sleigh rides along lantern-lit trails, as well as fire pits to warm up next to.
31. Portsmouth, NH
Best as a day trip from: White Mountains, Boston, Providence, Newport, Massachusetts North & South Shore, Portland and surrounding areas
Portsmouth is another destination in New England that feels like both a city and a quaint, charming town, and in the winter, it feels like the most perfect, cozy winter day trip adventure.
One of the top things to do in the city during the winter season is skate at the outdoor rink at Puddle Dock Pond, which is part of the Strawbery Banke Museum. The ice rink is backdropped by historic houses, and you can’t help but feel like you’re in a cute little New England village while you make your way around the ice.
After your skating adventure, you’ll want to walk through the beautiful historic side streets to Market Square, where you’ll find tons of beautiful stores and amazing restaurants for a cozy meal. One of the coolest places to eat in Portsmouth is the Book & Bar, which is, as you probably guessed, a bookstore, bar and cafe all in one.
Pro Tip: To stay warm while you explore, grab a hot chocolate from Elephantine Bakery before you begin your stroll around Market Square.
32. Boston, MA
Best as a day trip from: Providence, Portland, Cape Cod, Plymouth, Massachusetts North & South Shore, Newport
Boston is a wonderful city to visit year-round, but I actually think winter is one of the best seasons to explore because it’s far less crowded. Sure, the winter weather isn’t exactly idea, but if you get lucky enough to experience a fresh snowfall, it’s simply so beautiful to see the cobblestone streets covered in a dusting of snow.
Plus, because Boston has so many wonderful things to do indoors, as well as a few fun outdoor activities, it’s hard to beat for a city winter escape.
One of the best ways to get around Boston any time of the year is by trolley. This allows you to park your car for the day and have someone else take you to the best locations around the city. One option is the hop on/hop off pass, which is perfect for day-trippers.
→ Click here to book your Boston trolley passes!
And is it just me, or if your appetite bigger in the winter? I especially love food tours in the colder months for this reason, and Boston is an amazing destination to dive deep into the culinary world.
There are some awesome tours throughout the city to introduce you to the best foods in Boston, and you can click the link below to read my picks for the best ones.
→ Click here to check out my round-up of the best Boston food tours!
And for outdoor fun in the winter on your day trip, you’ll want to head to Frog Pond in Boston Common for ice skating, which is one of the best things to do in Massachusetts in the winter. This is especially fun at night when the rink is surrounded by twinkle lights, and you can see the city landscape light up as you make your way around the ice. You’ll also want to grab a cup of hot chocolate from L.A. Burdick to savor while you walk around to explore.
For indoor activities, you can visit the New England Aquarium, do some shopping at Copley Place, get tickets to a show, and make reservations for a fun dinner out before leaving (I’m especially fond of the Italian restaurants in the North End, but there are tons of places to choose from all over the city!).
33. Providence, RI
Best as a day trip from: Boston, Newport, Cape Cod, Plymouth
Providence is the capital of Rhode Island, and is a wonderful day trip to take in the winter season (and year-round, too!)! Not only will you get to enjoy everything the city has to offer in terms of great food, culture, theater, and historic sites, there are also some very fun ways to enjoy the winter season in Providence.
To enjoy the brisk winter weather, you’ll want to head to the BankNewport City Center Rink in downtown Providence. Here, you can enjoy ice skating and … ice bumper cars? Yes, you read that right! This rink is also home to this unique and fun winter activity that’s sure to make you feel like a kid again.
34. Killington, VT
Best as a day trip from: White Mountains, surrounding areas in Vermont
One of the best places in Vermont for skiing and outdoor winter fun is Killington Ski Resort, so this is the perfect day trip option for anyone looking to spend all day outdoors playing in the snow.
At Killington, you’ll find a large network of downhill ski trails, as well as a really fun snow tubing park, a roller coaster, snowmobile tours, snowshoe trails and even a spa (which is the perfect way to end your day trip after playing outside all day!).
35. Portland, ME
Best as a day trip from: Boston, Massachusetts North & South Shore, surrounding areas in Maine
Finally, let’s talk about Portland, one of the coolest destinations in Maine in the winter season. While Portland is also wonderful year-round, I especially enjoy it in the winter for the same reasons I like Boston in the winter – fewer crowds, and a bigger appetite to eat all the food 🙂
Portland is another incredible foodie destination in New England, and you’ll definitely want to consider a culinary tour during your day trip.
One of the best foodie tours in the city is this Old Port culinary walking tour, which takes you to some of the best spots in the most beautiful and historic part of the city!
Click here to book your Old Port Culinary Tour in Portland!
Other posts on Portland to help you plan your trip:
- Best Things To Do In Portland In The Winter
- Best Breweries In Portland, Maine
- Best Day Trips From Portland, Maine
Best New England Day Trips In New England For Families
Pretty much every destination on this list makes for a wonderful day trip with the kids, but here are my picks for places that are especially perfect day trips in New England for families. I’ve included a few kid-friendly suggestions for each destination to plan the perfect itinerary.
→ Boston, MA: New England Aquarium, Boston Children’s Museum, Boston Museum of Science, Legoland Discovery Center, boat ride at the Public Gardens, The Lawn On D.
→ Mystic, CT: Mystic Aquarium, Mystic Seaport Museum to climb aboard tall ships, B.F. Clyde’s Cider Mill (fall season), sail boat tours, watch the Bascule Bridge in action.
→ Woodstock, VT: Billings Farm & Museum is one of the top attractions for families in Vermont, Silver Lakes State Park, ice cream at Woodstock Scoops, horse-drawn carriage rides.
→ Providence, RI: Roger Williams Park Zoo, WaterFire events, Providence Children’s Museum, ice skating (winter), Water Place Park.
→ Block Island: 1661 Farm and Gardens, The Ice Cream Place, free beaches, and kids will love the ferry ride to get there!
Best New England Day Trips For Couples
As I’m sure you can imagine, all of the destinations from this list are amazing day trips for couples, but here are my picks that are especially perfect for a romantic day together:
→ Kennebunkport: This is a romantic destination year-round, and is especially perfect at Christmas, Valentine’s Day, or for a summer day trip.
→ Nantucket: The island is one of the most picturesque places in the U.S., and the beaches are absolutely stunning and offer incredible sunsets for a romantic stroll.
→ Stowe: Perfect for a fall or winter day trip, Stowe is such a quintessential New England town that’s cozy and romantic.
→ Litchfield, CT: Spend your day admiring fall foliage, covered bridges, eating at cozy restaurants and walking around quaint villages while holding hands.
You may also enjoy reading:
- Best Boston Hotels Near The Aquarium
- Most Incredible New England Resorts & Spas
- Summer In New England: Best Places To Go & Things To Do!
- Lovely Things To Do In New England In The Spring
- Exciting Things To Do In New England In The Fall
- Awesome New England Winter Getaways (Even For Non-Skiers!)
- 60+ Things To Do In Vermont
- The Most Incredible New England Lighthouses To Visit
- Summer In Connecticut: The Best Things To Do!
- The Perfect New England Fall Road Trip Itinerary
- Best Time To Visit New England
- My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
That’s A Wrap On The Best New England Day Trips
And there you have it! My picks for the best day trips in New England. So, where are you planning to go first? Maybe hit the beaches in Provincetown? Wander the historic streets in Boston? Regardless of where you go, one thing’s for sure – it’s going to be a memorable day!