16 Fun Road Trips from Boston Only A Short Drive Away

One of the best things about taking a trip to Boston is that there’s so much to do and it’s all so easy for you to get to. You can even take a day trip to New York and head back for the evening without having to worry about losing too much time!

In fact, arguably, the biggest challenge with planning a trip from Boston is narrowing down potential destinations. Plus, there’s an international airport to consider and the option of taking a cruise from Boston to see some of the world from the sea.

Here are a few of the destinations just a short drive away from Boston that you’ll want to consider, whether you’re a Boston resident or looking to book your next road trip. Pack some snacks for the family and hit the road!

This post is part of our North American Destinations Series – you can also read more great road tripping with kids ideas here

Trips from Boston: A short drive away

1. Plymouth

Plymouth, Massachusetts, shares its name with an old English seaside town, and it’s mostly known as the spot where the Mayflower docked and established a colony 400 years ago. There’s plenty of old architecture and historical monuments around Plymouth to see, and it also has a bunch of awesome museums and restaurants to visit.

Winter in Plymouth, Massachusetts // Image Credit DenisTangneyJr Via Canva

Plymouth is particularly magical around Christmas, making it one of our favorite winter destinations in the US.

2. Plimoth

No, this isn’t a typo, and you’re not going crazy. Plimoth Plantation is a sort of living exhibit where you can walk around at your leisure and experience what life would have been like as one of the pilgrims who first settled there.

This is especially a great option if traveling with kids. Many of the original machines and technologies were around at the time, making it a great way to learn a little more about history and where we all came from.

Check out these incredible Airbnb properties around New England to complete your road trip!

3. Portsmouth

Okay, now we’re just playing with you. Don’t make the mistake of getting these three very different destinations confused with each other. This coastal city is also named after an English counterpart, and it’s a great spot for everything from boat trips and fresh seafood to museums and theatres.

Portsmouth New Hampshire // Image Credit Sean Pavone via CanvaPro

Better still, it’s been growing and growing in recent years and now has the infrastructure to rival anything that any other city can throw at it.

4. Newport

Also named after a British place (this time in Wales), Newport is another stunning little coastal town with plenty to offer the casual visitor. In particular, we’d recommend strolling through Brick Market Place in the city’s downtown area, which is iconic for its delicious Chinese cuisine and the wide range of shops and stores that are on offer.

The Newport Mansion at Christmas is an unforgettable experience. And if you’re a car lover, you’ll want to stop by Portsmouth (also on this list) to visit the Newport Car Museum.

5. Newburyport

Seriously, what is it with these names? This coastal town has a lot in common with some of the others on this list, except that it’s a little less busy and so it’s easier for you to lose yourself in your own thoughts while wandering around the stunning scenery.

If you can get there in the summer, all the better – the street performers will be out in full force and the beaches will be just right for a bit of sunbathing. For a small town, there’s a lot to see and do in Newburyport.

6. Lincoln

Nestled at the base of the White Mountains in New Hampshire, there’s plenty to see and do in Lincoln throughout the year. In the winter, the town really comes alive, with a range of winter sports available as well as some of the most scenic ice skating rinks that we’ve ever come across. It’s a great place to take the kids if you’re looking for something magical in the run-up to Christmas.

7. Cambridge

Are you starting to see a theme here? Also named after our friends across the pond, Cambridge MA is just as intellectual as its British counterpart. As the home of Harvard, it’s also home to a bunch of different art galleries and museums that will satisfy even the most culture-obsessed travelers. And because even the smartest college students know how to party, there’s also plenty going on in the nighttime.

Kennedy Street in Harvard University Area, Cambridge MA // Image Credit RomanBabakin via CanvaPro

8. Providence

Located in Rhode Island, Providence is about an hour’s drive from Boston and makes for a great day trip if you want to see something a little bit different. It has regular festivals and celebrations throughout the year, so if you’re thinking about swinging by then it can be a good idea to spend some time looking at what’s coming up on the calendar; fall is a busy time with leaf-peeping road trippers in New England!

You’ll find plenty of fantastic places to eat, too. We recommend scoring some Italian food on Federal Hill.

9. Martha’s Vineyard & Nantucket

Martha’s Vineyard is one of only five US place names with apostrophes in the name, something which is technically against the law. In fact, it’s only been allowed to keep it because it has so much history, and that should give you a clue about why you might want to visit Martha’s Vineyard in the first place. And as you might expect from a place named after a vineyard, the food and drink scene is fantastic.

The Vineyard Island Martha’s Vineyard // Image Credit Cheri Alguire via CanvaPro

Nearby, Nantucket Island is known for its stunning beaches, picturesque lighthouses and crashing Atlantic waves.

10. Provincetown

Based on Massachusetts’ iconic Cape Cod, Provincetown is reminiscent of San Francisco in many ways because it’s a haven for artists, actors, musicians, and more, as well as a thriving LGBTQ+ community.

There are museums and art galleries almost everywhere you turn, as well as cool specialist stores and boutiques selling handmade goodies. There’s really nowhere else in Massachusetts that’s quite like it, and it’s sure to have something for everyone in the family.

11. New York City

As we mentioned earlier, New York City is just 4 hour’s drive away, and the city that never sleeps has so much going on that you could spend a month there and not run out of things to do.

Still, you can see quite a lot in a day trip or even spend the night there to give you a little more time – there’s plenty to see and do on the drive from Boston to New York City too; we’d strongly recommend extending your trip through Upstate New York.

Brooklyn Bridge to Manhattan // Image Credit sborisov via CanvaPro

You can read our family guide to exploring Manhattan here.

12. Castle Hill

You’d be crazy to skip a visit to this stunning 60-room mansion. You’ll feel as though you’ve stepped out of Massachusetts and into the middle of the English countryside. At only an hour’s drive away, it’s perfect for a half-day out. Pack a picnic and a blanket to enjoy lunch on the lawn.

13. Glendale Falls

Glendale Falls offers a great excursion by providing you with some of the most awe-inspiring natural beauty the state has. It’s one of the largest series of waterfalls in the country, and there are many trails to explore.

15. Concord

Concord is a relatively small town with a big history. It’s probably most well-known for being the site of a number of battlefields and as the haunting grounds of several key figures throughout history, including writers and statesmen. Walking through Concord, you know you’re retracing famous footsteps.

Minute Man National Historical Park, Concord MA // Image Credit jejim via CanvaPro

16. Lexington

Lexington is known for its battlefields too, including the iconic spot on Lexington Common where soldiers fired the first shot of the Revolutionary War. Many come in droves to learn more about the history of the area and the stunning country that we live in today. 

Want to extend your trip even further to Acadia National Park and the Maine coast? Try this road trip itinerary taking you all the way from Boston to Bar Habour on an epic new England Family road trip.

Planning your Boston day trips

Now that you know a few of the best places to visit while driving from Boston, it’s time for you to start planning your vacation. Remember, you can always combine multiple different destinations into a single trip by renting a car and going from city to city.

Because of that, it’s a good idea for you to go ahead and create a shortlist and an itinerary of your own, planning out where you’re going to visit, how long you’re going to stay, and which route you’re going to take.

By creating an itinerary and sticking to it, you can start to reserve hotels and other amenities to take advantage of early-bird pricing. This will save you money and also help you to avoid stressing too much in the run-up to your vacation. That way, you can just focus on having a fantastic time. Happy travels!

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