Boston and New York are the two most exciting cities to visit in the Northeast, and if you’re looking to visit both during an upcoming trip, I have some fantastic suggestions for you on awesome stops to make between the two. Having grown up and gone to college in New York State, and having spent the last 15+ years exploring the entire New England region, I’ve experienced quite a bit in this area, and know what’s worth your time, and what’s not.
To help you plan your drive from Boston to New York City (or vice versa), I’ve laid out three different routes you can take turning this drive to make it a true road trip style adventure to see as many amazing places as possible. Depending on how much time you have, everything can be customized to your own preferences and schedule, too.
Ready to start planning your road trip? Let’s go!
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How Long Is The Drive Between Boston & New York City?
Without any stops on the most direct route, the drive typically takes about 4.5 hours, without traffic. However, both Boston and New York are known for having a lot of traffic getting in and out of the cities, especially during rush hour. So usually, the drive will take about 5 hours or more, depending.
However, if you’re looking to turn this drive into a road trip adventure, it can take anywhere from a full day to a week. There are so many wonderful things to see on the Boston to New York drive, including the Berkshires region of Massachusetts, the New England coastline, and the Hudson Valley region of New York.
To explore these areas, you do have to veer off-course a bit, and not take a direct route – but I promise you, it’s so worth it if you have the time!
Is The Drive Scenic?
Yes and no. The stops you’ll make along the way will be incredible scenic and beautiful. However, most of the routes you’ll take will be on major highways that aren’t quite as scenic. Some parts of the drive, like through The Berkshires, for example, have gorgeous views to enjoy. However, plan to be spending most of your time on highways that aren’t quite as exciting.
This drive is more about the stops, which are very much worth your time!
Best Routes To Take Driving From Boston To New York
I’ve broken down the road trip into three different routes for you: Two of them involve going out of your way a bit to see some incredible places that are so worth the detour, and one of them is a more straight-forward, direct route with my suggestions on how to maximize your time with some cool stops on the way.
My suggested routes are:
The Coastal Route, which takes you south of Boston to Plymouth, Cape Cod and the islands, and then through the Rhode Island and Connecticut coast.
The Berkshires & Hudson Valley Route, which takes you west of Boston over to The Berkshires first, and then down through New York’s beautiful Hudson Valley region, before ending in the city.
The most direct route, which doesn’t include any detours that are out of your way, but some fun things you can do on the drive to make the most of your time.
Things to know about the coastal route, and the Berkshires/Hudson Valley route:
→ Both of these routes definitely take you a bit out of the way, and will add time to your drive. These were intended for those with extra time to make the drive who wanted to see some of the prettiest areas between Boston and New York City. However, based on how awesome the destinations are, it’s worth the short detour!
→ Each stop is a suggestion based on my experience driving around the area, and everything can be tailored to your schedule and preferences! Definitely be sure to create an itinerary that suits your travel style, and the amount of time you have, using the information in this post about each stop. It’s not necessary to make every stop on each route, especially if it doesn’t sound like something you’d personally be interested in.
→ As mentioned, you’ll need to plan some extra time to drive in and out of the cities. There’s always traffic in both Boston and New York, and the drive time is usually more than Google Maps says.
→ For the reason mentioned above, I recommend trying to avoid rush hour in both Boston and New York, if your schedule allows it. This is the worst time to drive around both cities, and you’ll add a lot of extra time just sitting in traffic.
Stops To Make On The Boston To New York Drive – Coastal Route
There are so many beautiful coastal towns to experience when driving from Boston to New York City, and this route stops at the ones that I think are most worth your time. Many of these destinations are worthy of at least a few nights on their own, and I’ve noted under each suggestion how long you need, and if it’s recommended to visit for a few hours, or a night or two.
1. Plymouth
The first stop just south of Boston is Plymouth, and what I always tell people is – it’s so much more than a rock! Yes, there’s lots of history here, including the famous Plymouth Rock, but it’s also home to lovely parks, beaches, a charming downtown area, great restaurants, and one of New England’s best resorts and spas – Mirbeau.
If you’re looking for a little pampering on your road trip, visiting Mirbeau Inn & Spa is a great place to stop. You can spend a full night here and book a room at the cozy inn, or stay for a few hours to indulge in spa treatments, and take advantage of their spa facilities and wonderful Bistro for lunch.
If the spa scene isn’t your vibe, Plymouth is still worth a visit! I really love walking around the Brewster Gardens, hitting up the shops on Main Street and the Shoppes at Village Landing, walking along the waterfront, and doing a wine tasting at Plymouth Bay Winery.
And of course, there’s an excellent museum infrastructure in Plymouth, and I recommend getting a combo ticket to the Mayflower II and Grist Mill. The Mayflower II is an exact replica of the original ship, and with a ticket, you can hop aboard for a closer look. The Grist Mill is also a very cool experience.
Psst! I have some more detailed posts on visiting Plymouth, MA, and if Mirbeau in Plymouth is worth it, if you’re looking for more info 😉
Time needed in Plymouth: Anywhere from a few hours to walk around and visit a museum or two, or overnight.
2. Cape Cod
Southeast of Plymouth is the beautiful Cape Cod peninsula, which is known for having the most stunning beaches in the northeast, as well as quaint towns, lighthouses, and fantastic dining. This destination is a bigger region than most others on this list, and does require more time to visit, but it’s definitely worth it if you’re interested in seeing some of the best coastline in New England.
Home to 16 towns, each with their own unique character, there’s plenty to see and do here, but the most beautiful area of Cape Cod is definitely the Outer Cape, which is the eastern shoreline along the Atlantic. This area is also home to the Cape Cod National Seashore, which has six beaches, nature trails, and lighthouses. Along with that, I especially love visiting the towns of Chatham and Provincetown, popping into all the very cool shops, and dining on the waterfront.
Psst! I have lots of posts on Cape Cod that may help you plan your trip. Here are a few to get you started:
→ Visiting Cape Cod For The First Time
→ Best Things To Do On Cape Cod
→ Best Towns To Stay In When Visiting Cape Cod
Time needed on Cape Cod: This stop is best for those who are able to stay the night, as the region requires more time to explore. However, if you have a full day, it can also be done in a day. It’s not one I recommend if you only have a few hours.
3. Nantucket & Martha’s Vineyard
Just off the coast of Cape Cod are two stunning islands that are very worthy of your time during your road trip: Nantucket and Martha’s Vineyard. Also known for gorgeous beaches and charming towns, there’s so much incredible scenery to enjoy while visiting both islands, and I highly recommend them if you have the time.
Both islands are easy to visit as a day trip from Cape Cod, and you’ll need to hop aboard a ferry to get over, as there’s no bridge to either island. Depending on which island you want to visit, you’ll have different options for departing locations, so you’ll need to plan accordingly.
While both islands are so gorgeous, I usually tend to recommend Nantucket for day trippers more, simply because it’s a bit easier to manage during a day trip. However, you can’t go wrong with either!
Psst! I have lots of posts on visiting the islands, and here are a few to get you started:
→ Nantucket vs. Martha’s Vineyard For A Day Trip
→ Nantucket Day Trip Guide
→ Martha’s Vineyard Day Trip Guide
Time needed on Nantucket or Martha’s Vineyard: Both islands can be done as a day trip, as mentioned, but you’ll need a full day for each. They can also be done as an overnight trip. Keep in mind that many hotels have a 2-night minimum stay requirement in the summer season.
4. Newport
Heading into Rhode Island, Newport is one of the best stops you can make in the Ocean State. Known for its Gilded Age mansions, historic and charming downtown, and oceanfront scenery, it really has it all.
Lovingly referred to as the City By The Sea, one of my favorite ways to enjoy Newport is by strolling along the Cliff Walk, which is a paved pedestrian path along the ocean that offers some of the best views in the city. You’ll also pass by some of the mansions on the walk, offering the best of both worlds.
During my visits, I always schedule some time to also explore the awesome downtown area, which is filled with shops and restaurants. Bowen’s Wharf, Thames Street, and the historic areas are such a treat to take in during your visit!
If you have time, I also recommend driving the very scenic Ocean Drive for awesome coastal views, and heading out onto the water for a boat or sailing tour.
Psst! I have a post all about taking a Newport, RI day trip, if you need more ideas 😉
Time needed in Newport: Can be done in a half day, full day, or an overnight stop, depending on your preferences.
5. Narragansett And A Block Island Day Trip
Further along the Rhode Island coast is the lovely town of Narragansett, and just off the coast is the wonderful Block Island. Depending on how much time you have, both are worth a stop!
Narragansett is an oceanfront town, and has a nice little walking path along the water, some great restaurants, and a beach. If you only have time for a quick stop, I recommend looking for parking around the historic Two Towers, and dining outside at Coast Guard House Restaurant, which is right along the walking path.
If you have more time and want to head over to Block Island, this will make for a very fun day! Block Island is pretty small and very easily managed as a day trip. The ferry to the island is located in Point Judith, which is a village in Narragansett, and depending on which ferry you reserve, it takes anywhere from 30-60 minutes to get to the island.
While on Block Island, I recommend exploring the quaint downtown, which is where the ferry drops you off, visiting the Mohegan Bluffs staircase and beach, the lighthouses, and having lunch overlooking the water at The Oar.
Psst! I have a detailed guide on taking a Block Island day trip, if you’d like more info 😉
Time needed in Narragansett and Block Island: A full day if you plan to visit Block Island, but you can easily spend just a few hours if you only visit Narragansett. In fact, Narragansett alone can be done in about an hour if you just want to stretch your legs and walk along the water for a bit.
6. Matunuck Oyster Bar
If you’re in the area and are looking for a fantastic place for lunch or dinner, look no further than Matunuck Oyster Bar! Pronounced Mah-TOO-nik, this amazing restaurant sits right on Potter Pond, which is where their oysters are harvested from. Everything here is incredibly fresh, delicious, and locally harvested from either the pond or garden (in season). It’s truly such a special experience!
During your visit, you can also book an oyster farm tour before or after your meal, where you’ll get a closer look at the shellfish grown and harvested in the pond. Nearby the restaurant is East Matunuck State Beach, which is perfect for taking a walk on the shore, or going for a dip in the water.
Time needed at Matunuck Oyster Bar: 2 hours for dining, plus any time you need to take a tour, or at the beach down the street (additional fees may apply in season for parking at the beach, plan accordingly).
7. Westerly & Watch Hill
Almost to the border of Connecticut, Westerly, RI is another worthy stop to make on your coastal drive from Boston to New York. Also included in this stop is the charming village of Watch Hill, most known for being the home of Taylor Swift’s East Coat beach mansion.
Westerly has a cute little downtown area to explore, an awesome brewery, and the very nice Misquamicut State Beach. During your visit, I highly recommend heading over to Watch Hill, which is the most charming part of Westerly. You’ll find a small little shopping area, a lighthouse, beautiful coastline, and the famous Ocean House hotel, which is a great spot to splurge on lunch or dinner.
I always like to remind folks that Watch Hill parking can be tough, especially in the summer season, and on weekends. There’s a two-hour limit to parking here, if you’re able to snatch up a spot, otherwise, you’ll need to pay to park at one of the small lots. It’s worth the effort, but keep in mind you may only have two hours to walk around, which is enough time in Watch Hill if you don’t plan to stop and eat.
Psst! I have a detailed guide on visiting Westerly, RI, if you’re looking for more information.
Time needed in Westerly & Watch Hill: Anywhere from 2 hours, to a half day. Stopping here for the night will be very expensive, but it can also be done an an overnight if you’re looking to splurge.
8. Mystic
Heading into Connecticut, one of my favorite towns in this area is Mystic. While it’s known for the movies that have filmed here, it’s such a fun town to explore for its maritime charm, walkability, and great shops and restaurants.
One of the top attractions is the Mystic Seaport Museum, which I highly recommend! I’m actually not a big museum person, but love the Seaport. Most of the museum is located outdoors along the river, and includes an authentic, historic village, and tall ships you can climb into. Click here for ticket information to the Seaport!
Downtown Mystic is also wonderful, and there’s a great Main Street right by the river with lots of cute shops and eateries to check out. Be sure to swing into Swift Bakery and get some treats for the road!
Lastly, I also suggest heading over to the Olde Mystik Village shopping area, which is an outdoor plaza that looks straight out of a Hallmark movie. Oh wait, there actually was a Hallmark movie filmed here! If you happened to see Mystic Christmas on the Hallmark channel, this area will look very familiar 😉 I actually got to see this plaza set-up for the movie filming during one of my visits, which was very cool.
While at Olde Mystik Village, one of the coolest places to visit is the Potion Bar at Cloak and Wand to get a fun and creative drink.
Psst! I have a guide on things to do in Mystic, CT, if you’re looking for more ideas.
Time needed in Mystic: Anywhere from a quick 1-hour stop, to half a day will allow you to see the town. You can also choose to spend the night here.
9. Niantic
Niantic is a more under-the-radar destination along the coast, but I honestly think it’s such a wonderful coastal town to visit on a road trip, even if just for an hour or two.
Niantic sits along the bay, and one of the best things to do in town is walk along the boardwalk to soak in the water views. Most of Main Street also runs parallel to the water, so you’re never very far from it, which adds to the appeal of visiting.
There’s also a quaint downtown area, one of the best used bookstores in New England, and also, another Swift Bakery location can be found here, so be sure to pop in to get some things for the road!
Psst! I have an entire guide on things to do in Niantic, if you need more ideas.
Time needed in Niantic: Anywhere from 1-4 hours, depending if you want to eat.
10. Old Saybrook, Essex & Chester
I’ve grouped all of these towns together because they’re pretty small, and you can easily see them all in one day, or even less. However, just because they’re small, doesn’t mean they’re not worth a stop! Each of them packs in a lot of character and New England charm, and offers some really cool things to do.
Old Saybrook is a great town with a large Main Street for shopping, museums, parks, and waterfront dining. I really love to dine on the water at the Saybrook Point Resort & Marina, pop into the shops on Main Street, and enjoy the water views from the Causeway when visiting.
Essex is such an adorable town to visit, and is a great stop to make when driving Boston to New York if you’re looking to visit a town that resembles Stars Hollow. There are some great little shops on Main Street, a nice harbor to enjoy water views, and a cozy inn that has a wonderful restaurant!
Chester is not far from Essex at all, and is another Stars Hollow-esque town to see. The idyllic scenery is backdropped by fantastic restaurants, shops, and a brewery, and while it’s very, very small, it definitely feels like the set of a Hallmark movie.
Psst! I have guides for all three of these towns to check out:
→ Things To Do In Old Saybrook, CT
→ Things To Do In Chester, CT
→ Things To Do In Essex, CT
Time needed in Old Saybrook, Essex, and Chester: You can see each with just 1-2 hours, plus more if you plan to stop and eat.
11. Guilford
Lastly for charming towns in Connecticut, Guilford is another one of my favorites that’s also a bit under-the-radar. This cute little town is centered around a beautiful Town Green park, and lined with wonderful shops, eateries, and historic buildings on each side.
When visiting Guilford, some of my favorite places to visit are The Village Chocolatier, Cilantro Specialty Foods for a quick lunch or coffee/tea, Breakwater Bookstore, and Lake Quonnipaug for a bit of relaxing.
There are also lots of historic buildings open to visitors in town, including museums and beautiful colonial homes.
Time needed in Guilford: 1-2 hours, plus more if you plan to stop and eat.
12. Silver Sands State Park
Located in the town of Milford, CT, I really love to visit Silver Sands State Park, especially as a road trip pit stop because it’s a great way to get out of the car, stretch your legs, and take a walk.
This park has a long boardwalk that runs along the water, which offers really nice views along the way. At low tide, you can also walk out onto a sand bar over to Charles Island, which is a really fun activity!
The only downside to visiting is that state parks in Connecticut charge decently hefty fees for out-of-state residents. While it’s free for Connecticut residents to visit any state park, out-of-staters will have to pay to enter in-season. However, if you happen to visit outside of the high season, it’s free for all to visit! Click here for more info.
Time needed at Silver Sands State Park: 1-2 hours.
13. Stew Leonard’s In Norwalk
I know, it’s just a grocery store, but hear me out!
Stew Leonard’s a boutique chain of grocery stores in Connecticut, New Jersey, and New York, with only eight locations. And the chain is known for having a quirky and fun vibe, selling its own dairy (including handmade cheeses!), and they have their own ice cream area with delicious soft serve. Think of it as kind of like Trader Joe’s, but bigger (and honestly, a little better in many ways).
While they sell a variety of known brands, too, you’ll want to scout out all the Stew Leonard’s stuff, including donut holes, kettle chips, cookies, and so much more. And, if you happen to spend $100 in groceries, you get a free soft serve on your way out.
Time needed at Stew Leonard’s: 1 hour at most.
14. Greenwich
The last stop on this route is Greenwich, CT, which is a beautiful town pretty close to New York City, so you’re almost done with your road trip!
In Greenwich, you’ll find lots of historic New England charm, as well as a vibrant but cozy downtown area with lots of shopping, beaches, and parks to visit. It’s a great stop to make when you need to get out and stretch before heading into the city.
When I visit Greenwich, I really love to walk the trails at both the Fairchild Wildflower Sanctuary and Greenwich Audubon Center, pop into downtown to visit the shops, and grab a latte from Love You a Latte, and then head to Greenwich Point Park to enjoy the water views. Keep in mind that Greenwich Point charges out-of-staters an admission fee May 1-October 31, so you’ll want to plan accordingly.
Time needed in Greenwich: 1-4 hours, depending on if you want to explore some of the trails, or have lunch.
Driving Boston To New York – Berkshires/Hudson Valley Route
If the countryside and mountains are more your jam, then you’ll want to consider taking the drive through The Berkshires in Massachusetts, and the Hudson Valley region of New York State. Both of these regions have more rural scenery to enjoy, farm stands, small towns, and lots of cool things to check out.
While this route requires you to drive a bit further west from Boston at the start, you’ll shoot right down New York to the city from there. Getting to visit these two regions is such a treat, and worth the extra time! Here are the most note-worthy stops to make along the way.
15. Tree House Brewing, Charlton
The first stop you’ll make on this route is Tree House Brewing in Charlton, which is about 1-1.5 hours from Boston (depending on traffic). If you love good craft beer, this is a must! Tree House is easily my all-time favorite brewery in New England, and you can only get their beers at their brewery locations – they’re not sold in stores. Since there are only five locations in the northeast (with a sixth one coming to New York State soon!), this is a worthy stop to make.
The location in Charlton is a destination in and of itself – the sprawling building and beautiful grounds make it perfect year-round, and the entire facility is pet-friendly, which is so refreshing. The outdoor space is sprinkled with Adirondack chairs in a wooded area, and they also have a covered pavilion, which has fire pits going in the winter.
Pro Tip: It’s good to know that the Charlton location does get rather busy, especially on weekends in the summer and fall, so you’ll want to plan ahead if you happen to visit during these times. The lines for the draft pours can get pretty long, and they recommend getting two drinks at a time if the lines are long. Just know it’s worth it! Their Julius IPA is one of the best I’ve ever had. Ever.
Time needed at Tree House: 1-2 hours to enjoy a pint and the atmosphere.
16. Sturbridge, MA
Very close to Charlton is Sturbridge, and there are two main reasons this is worth a stop on a road trip: Old Sturbridge Village, and Saw Dust Coffee House.
Sturbridge is a pretty small town, and everything is more spread out – meaning there’s not really a walkable downtown. However, stepping into Old Sturbridge Village, that changes. This living museum recreates life in New England during the early 1800s, and you truly feel as though you’ve stepped back into time. You’ll discover historic houses, demonstrations, scenic trails, covered bridges, and even an on-site mercantile and café. It’s easy to spend at least a few hours here, and it’s such a unique experience that I enjoy every time I visit.
Depending on when you visit, they also have seasonal events throughout the year, including their very fun Phantoms by Firelight in the fall, and Christmas by Candlelight during the holidays.
Pro Tip: It’s good to know that Old Sturbridge Village has abbreviated hours in the winter, so be sure to check before making a special trip.
Time needed in Sturbridge: 2 hours to walk Old Sturbridge Village, and a few extra minutes to grab something to-go at Saw Dust.
17. Lenox, MA
Heading into The Berkshires region of Massachusetts, the charming town of Lenox will be your next stop on your drive from Boston to New York. While this town is wonderful to visit year-round, I especially love it in the fall season for a few reasons, which I’ll get into in a bit 😉
First, Lenox has a small, walkable downtown area with some cute shops and cafés, so it’s an easy stop to make to enjoy the scenery. There’s also The Mount, which is the historic estate that once belonged to famed writer Edith Wharton, and it’s a wonderful way to spend a couple of hours.
The fall foliage in Lenox is also so beautiful, which is why autumn is my favorite time of year to visit. The streets around downtown are lined with trees that are bursting with color in the fall, and the relaxing trails through the Pleasant Valley Wildlife Sanctuary are also especially beautiful during foliage season.
There are quite a few other fantastic things to do during your visit, including picking up locally handcrafted chocolates at Chocolate Springs (I also love their hot chocolate!), explore the Ventfort Hall Gilded Age Mansion, or take in a show at Tanglewood if your timing works out.
Time needed in Lenox: 1-4 hours, depending on what you plan to do.
18. Stockbridge, MA
Not far from Lenox is another quaint and idyllic town in The Berkshires, which is Stockbridge. This town was made famous by the artist Normal Rockwell, who memorialized the picturesque Main Street during the Christmas season in a now iconic painting. And honestly, Main Street doesn’t look much different now, which is why it’s such a treat to visit Stockbridge!
While the Main Street area is very small, there are some really great shops and cafés to enjoy along the two blocks or so, including Williams & Sons Country Store, Love Peace & Chocolate, and the Lost Lamb patisserie. Be sure to also walk by the iconic Red Lion Inn.
The Normal Rockwell Museum is also a really great place to visit, and you’ll also find scenic trails around the grounds to enjoy that are especially beautiful during fall foliage season. Lastly, the Naumkeag estate is also a wonderful place to experience, and they often have seasonal events taking place, including a pumpkin show, and a festive Winter Lights event.
Time needed in Stockbridge: 1-4 hours, depending on if you choose to tour the historic estates or museums.
19. Great Barrington, MA
Next in The Berkshires is Great Barringtown, which is a wonderful town to visit that’s a bit bigger and more bustling than Lenox and Stockbridge. However, it’s still filled with character, and a worthy stop to make on your road trip.
Along Main Street, you’ll have your choice of more shops, eateries, and cafés, so if you’re looking for a place to stop that has more food options, Great Barrington has you covered!
While in the area, I also really like to explore Monument Mountain Reservation, which has some great hikes with awesome views of the region. Windy Hill Farm is also a really lovely little garden center located just outside of town in the countryside, and they have some cute things, in addition to apples and cider donuts in the fall season.
Time needed in Great Barrington: 1 hour, or a bit more if you stop to eat or take a hike.
20. Upper Sheffield Covered Bridge, MA
From Great Barrington, you can easily head straight over to Hudson (the next stop) to save a bit of time, but if you love the charm of covered bridges, you may want to make the detour down to the Upper Sheffield Covered Bridge, which would be your last stop in The Berkshires.
These structures are one of the most iconic emblems of New England, and they make for a great little pitstop and photo opportunity on a Boston to New York road trip. Upper Sheffield is located just off Route 7, so if you have the time to head a bit further south, this is a worth a stop!
Time needed at Upper Sheffield Covered Bridge: 15-20 minutes.
21. Hudson, NY
Welcome to New York State!
Your first stop in New York is Hudson, and this wonderful town has a very long street that’s just absolutely packed with restaurants, cafés, antique stores, and boutiques. Warren Street is where you’ll want to head to when visiting, and it spans for about seven blocks, which means you can end up spending a lot of time here if you have it.
Hudson is actually so cool and fun to visit, it’s not uncommon to spot celebrities strolling around, too.
Time needed in Hudson: 1-3 hours, depending if you stop to eat.
22. Saugerties Or Rhinebeck, NY
Next up in New York is Saugerties or Rhinebeck, and I give you a choice because both are pretty similar, but one is a bit more out of the way.
While I love both, I do slightly prefer Rhineback, which is unfortunately the town that requires more of a detour. However, the charming and idyllic downtown area is very walkable, and filled with lovely shops and eateries. You can also swing by the Mirbeau Spa Rhinebeck location if you’re looking for an afternoon of pampering on your road trip!
Saugerties is another wonderful way to experience an upstate New York town filled with character, and this one is more on your direct route down to the city. Saugerties has a cute little downtown area with shops and restaurants, a beautiful lighthouse, and relaxing trails at the Esopus Bend Nature Preserve.
Time needed in Rhinebeck or Saugerties: 1-3 hours, depending on if you stop to eat.
23. New Paltz, NY
I may be a bit biased, but I think New Paltz is a must-see on your road trip, and it’s not just because I went to college here 😉
This wonderful little college town not only has a nice downtown area with great restaurants and shops, but it’s also home to the very famous Mohonk Mountain House. Mohonk is a victorian castle nestled into the mountains, and is one of the coolest experiences you can have in the region. If you stay overnight, it’s an all-inclusive resort, where food is included in your stay. However, they also have day pass options to enjoy the hiking, dining, and water sports available on the gorgeous grounds.
If you don’t have time to spend the day at Mohonk, it’s still worth a stop in New Paltz to stroll around town, visit the shops and such, see Historic Huguenot Street, and maybe squeeze in a hike in the nearby Minnewaska State Park.
Psst! I have an entire post about Mohonk Mountain House day passes, if you’re looking for the best options during your road trip.
24. Walkway Over The Hudson, NY
One of my favorite things to do in the Hudson Valley is the Walkway Over The Hudson, which is a bridge that crosses the Hudson River, and connects the towns of Poughkeepsie and Highland. The bridge itself is just over a mile long, but the trail continues much further than that once you walk off the bridge.
However, while on a road trip, this is such a fun stop to make to get out, stretch your legs, and enjoy scenic views of the Hudson Valley. It also makes for a very cool photo opp!
Time needed at the Walkways Over The Hudson: 1 hour or less, depending on how fast you walk 😉
25. Harriman State Park, NY
The last stop on this route before getting to New York City is Harriman State Park, which is the second largest park in the state. Spanning over 47,000 acres, it’s home to 200 trails to explore, 31 lakes to enjoy, and lots of scenic roads to drive around, making this absolute worth your time during your drive from Boston to New York. It’s a nice way to enjoy nature before getting into the city!
If you’re visiting in the summer, you can rent a kayak or canoe from Baker Camp, and head out on Sebago Lake. If that’s not something you have time for, there are tons of short trails that will allow you to stretch your legs, but get back on the road in no time. Some of the easier, shorter trails to check out are the Hessian Lake Loop, Breakneck Pond Loop, and the Twin Forts Trail.
Time needed at Harriman State Park: At least 2 hours, but 4 hours would be ideal to really enjoy it. Keep in mind you’ll need to pay an admission fee to enjoy the park.
Stops To Make On The Boston To New York Drive – Direct Route
For those who need to get between the two cities as quickly as possible, but still want to make some fun stops on the way, I’ve got you covered! This route doesn’t make any detours to save you as much time as possible, but I’ve noted the best places to stop so you can squeeze in a few adventures along the way.
Google will give you two options on this drive, and when you get to Trumbull, CT, hop on Route 8 instead of Route 15, which will take you to I-95. I think this route has more interesting things to do along the way without sacrificing much time, but the choice is yours!
26. Sturbridge, MA
As mentioned in the last section, Sturbridge is a really great stop to make, and if you have time to explore Old Sturbridge Village, it’s worth it! However, you can also just make a quick stop at Saw Dust Coffee House for a drink on the way if you don’t have much time to spare.
27. West Rock Ridge State Park, CT
Right in New Haven, CT, West Rock Ridge State Park is a great one to see that’s right on the drive to New York. Offering wonderful views of the surrounding area, you can easily make this a short visit by driving to the South Overlook, and enjoying views of New Haven from above.
However, you have a bit more time, there are several trails you can tackle here that offer views of New Haven Harbor, and Long Island Sound. You can easily make it as short or long of a stop as needed.
28. Sherwood Island State Park, CT
Another wonderful park that’s easy to visit when short on time is Sherwood Island State Park. Located in Westport, this coastal park offers really nice views of Long Island Sound, and has walking trails, a small beach area, as well as wetlands and woodlands to enjoy.
Since Sherwood Island is just off I-95, you won’t have to go very far off-course to enjoy the scenery! You can also take a short walk from the parking area to the coastal path pictured above to save time, or spend more time walking around to see more of the park.
29. Maritime Aquarium At Norwalk, CT
Also just a few minutes off I-95 is the Maritime Aquarium at Norwalk in Connecticut. I haven’t personally been to this aquarium yet, but I’ve heard wonderful things from folks who have, and it also has high ratings on Google and TripAdvisor.
While this stop will require a bit more time to walk around and enjoy seeing all the exhibits, it’s definitely one of the more fun stops to make. They have a giant Pacific octopus, jellyfish, meerkats, sea turtles, harbor seals, and so much more to enjoy!
30. Stew Leonard’s In Norwalk, CT
Just a few minutes off I-95, you’ll also find Stew Leonard’s in Norwalk, which I mentioned earlier in this post. If you’ve never been to this very fun grocery store, it’s worth a stop, especially if you plan to swing by the aquarium in town.
Be sure to read my section on this above to get all my suggestions on things to get while here 😉
31. Greenwich, CT
The last noteworthy stop you can make on this direct route from Boston to New York City is Greenwich, CT, which I also mentioned earlier in this post. This can easily be done as a shorter stop in an hour or less if you just want to explore the charming Main Street, but I also recommend checking out the beautiful parks if you have the time.
Editor’s Note: For any park and attraction I’ve recommended on this list, please be aware that there will be admission fees to enter. You’ll want to be aware of cost, and whether or not that particular park or attraction accepts credit cards so that you arrive prepared.
Best Towns To Stay Overnight In On This Drive
If you’re looking to make this a multi-day road trip, and are wondering what the best stops are between Boston and New York City, these are the ones I recommend based on hotel and restaurants options, as well as things to do:
Cape Cod: Because this region is so large, I mentioned earlier in the post that you really want to stay here for at least one night on this road trip to make the most of your time.
Great Hotels On Cape Cod To Check Out:
→ Inn On The Beach
→ Pelham House Resort
→ Chatham Bars Inn
Newport, RI: There are so many wonderful hotels, restaurants and shops to experience, plus such a wide-array of attractions and activities in Newport. This is a fantastic place to spend the night!
Great Hotels In Newport To Check Out:
→ Chart House Inn
→ Mill Street Inn
→ Serenity Inn
Lenox or Stockbridge: These two towns are only 10-15 minutes from one another, so you can pick either. While small, they have cozy places to stay (Lenox has more options, though), quaint places to dine, and notable things to check out.
Great Hotels In Lenox & Stockbridge:
→ Red Lion Inn
→ Lenox Collection Cozy Inns
New Paltz: Staying overnight at Mohonk Mountain House is such a treat! It’s definitely a splurge, and there could be a two-night minimum during certain times of the year, so keep that in mind. But if it works out with your plans and budget, it’s worth it to just do once in your life.
→ Click here to check rates & availability at Mohonk Mountain House
While these are just my suggestions, most towns and destination on this list will work for an overnight stay, so definitely book what feels right for your own plans and itinerary!
Which Route Should I Take On This Drive?
If all three route suggestions appeal to you, I’m happy to share some insight!
Take the coastal route if you’ve always wanted to explore the New England coast. You’ll see some stunning parts of the region along this route, as well as a mix of charming towns. This option is best of you have at least 3 days to make the drive, as there’s just so much to see. However, a week would be ideal.
Take the Berkshires/Hudson Valley route if you prefer a more mountain/rural vibe. You’ll also visit some quintessential New England towns with idyllic scenery, and get a taste for the beautiful Hudson Valley region of New York, which is known for small towns and beautiful rural scenery. This option is best if you want to take on more hiking and nature during the road trip. I’d suggest at least a fews days to make this drive, too, but 5-7 days would be ideal.
Lastly, take the direct route if you’re short on time. Admittedly, it’s not the most exciting of all three options, but there are still some cool places to check out on the way!
More posts you may enjoy:
- Things To Do In Upstate New York In The Fall
- My Ultimate 7 Day New England Road Trip Itinerary
- My PERFECT New England Fall Foliage Road Trip Itinerary
- Wonderfully Romantic Getaways From Boston
That’s A Wrap On The Boston To New York City Drive!
And there you have it! All my suggestions on the best places to stop on the Boston to New York City drive. Whether you’re looking to turn this into a multi-day adventure, or you have a short amount of time, hopefully this list shows you just how beautiful this area is, and how many wonderful things there are to see up this way. Happy planning!
