16 Fun Road Trips from Boston: 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 just a few of the destinations just a short drive away from Boston that you’ll want to think about, whether you’re a Boston resident or if you’re 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 on road tripping with kids 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 to see, and it also has a bunch of awesome museums and restaurants to visit.

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

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. There are many of the original machines and technologies that were around at the time, making it a great way to learn a little more about history and where we all came from.

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. 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.

Portsmouth New Hampshire // Image Credit Sean Pavone via CanvaPro

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. And if you’re a car lover, you’ll want to stop by Portsmouth (also on this list) to visit the Newport Car Museum.

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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.

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 on 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 night-time.

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

9. Martha’s Vineyard

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

10. Provincetown

Based in Massachusetts’ iconic Cape Cod, Provincetown is in many ways reminiscent of San Francisco 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.

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11. New York City

As we mentioned earlier, New York City is just a couple of hours’ 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. If nothing else, you’ll be able to stop by Times Square and Central Park.

You can read our family guide to exploring Manhattan here.

Brooklyn Bridge to Manhattan // Image Credit sborisov via CanvaPro

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 that the state has to offer. 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. When you walk through Concord, you know that 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. 

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 for and which route you’re going to take.

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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 on the run-up to your vacation. That way, you can just focus on having a fantastic time. Happy travels!

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