The 9 Best New England Road Trip Destinations

Taking a road trip through New England offers a look at beautiful landscapes and a chance to learn about American history. What are the best New England road trips?

New England has numerous drives and places to visit, including Boston, Salem, Gloucester, Rockport, and many other cities that are worth both a long or short drive and a day or two stays. The northeast has plenty of history and sightseeing to be done – you’ll have a hard time picking where to spend your time.

Let’s talk about which places to go in New England and what to see. We have a lot to cover here as New England is a fairly large place with lots of cities and places to visit. 

Where should I go for a New England road trip?

Boston, Massachusetts

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We are starting with Boston because the historic city is one of the most popular destinations for road trips. Boston is actually on the coast, so you might end up driving through a whole state and lots of cities to get there, but your ultimate stop might be Boston anyway!

Boston offers a huge variety of things to do, whether you are seeking history, eats, sports, or scenic views. 

Boston for Sports fans

Fenway Park is home to the Boston Red Sox, one of the most popular and historic teams in baseball. Head into Boston to watch a game and take in a tour of the stadium. 

You’ve also got the Boston Celtic basketball team playing later in the year and of course, Boston Bruins hockey in the winter into the spring.

Boston History

Boston’s Freedom Trail is a path that connects many of Boston’s historical sites ranging from churches to museums and meeting houses that were involved in the American revolution – it’s also only 2.5 miles and fairly easy to navigate on foot. 

Outside of the trail is Fanueil market, a red brick building that is still a market – and served as a public speaking place that riled up colonists during the revolution. 

You can also see the home of Paul Revere, who infamously rode the streets (he was among many!) and warned of an incoming British invasion, lighting a lamp from Old North Church – which is one of the oldest churches in Boston after being built in 1723.

Places to eat in Boston

While we won’t throw in any particular restaurants, we’ll say that Boston is well known for its selection of breweries and seafood. 

As a coastal city, you’ll be able to find freshly caught fish like clams, shrimp, lobster, and tilapia. Bostonians have been cooking with fish for generations, and they know how to do it!

Salem, Rockport, and Glouchester

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Salem and nearby cities are well known for their historic witch trials, though they have other things going on, too, of course.

As a harbor city, you’ll be able to find maritime history here, too, with several  museums and ships offering tours and lots of information about sailing from the 1700s.

Gloucester is a great place to spend a day at the beach when it is warm out. 

Of the available beaches, we recommend Wingaersheek for younger families because the tide and waves are smaller, making it less dangerous for kids. 

Overall, Gloucester is a fairly relaxed place outside the business of Boston, where you can find great seafood in the presence of the Fishermen’s Memorial Monument, which is a statue standing at the helm of a ship’s wheel.

Rockport’s physical attractions are well described within it’s name, as the city is basically an enormous hunk of granite that sticks out into the bay. 

The result is a beautiful but rocky coastline with fishing readily available. There are also many small, locally owned shops in this historic town, in addition to a couple of beaches that don’t tend to get overly crowded.

New Hampshire’s Coastal Byway

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The coastal byway in New Hampshire isn’t very long at just about 20 miles, but the trip there is worth it, and there is enough to do to spend a whole day. 

The boardwalk at Hampton Beach offers plenty of activities for kids and adults in addition to great seafood and views. 

During the summer, Hampton Beach also has live entertainment, including music readily available at outdoor restaurants and on the boardwalk.

The byway offers access to New Hampshire’s beaches, complete with stellar views of the Atlantic most of the way. You’ll also see many homes built in the 1700s and 1800s with the opportunity to slow down and see some architecture, as the roads aren’t all that busy.

Portland, Maine

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Portland is only a couple of hours north of Boston and makes for a quick and easy trip. One of Maine’s state mottos is “The Way Life Should be,” which is a feeling you might soon experience once you get a look at the coastline and history of Portland. 

Portland offers many lighthouses and historic museums from the early days before the revolution. 

You should also check out the Victoria Mansion, a brownstone home built in the 1860s, which offers a glimpse into what a glamorous life would look like in pre-civil war America.

Like many other New England cities, Portland is well known for its seafood. You’ve probably heard of Maine as being a prime source of lobster.

When you are there, look up the best lobster restaurants in the city and enjoy with a side, or a lot, of butter.

Bar Harbor, Maine

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Bar Harbor isn’t a big town, with a population of about 5,000. 

Bar Harbor is instead home to Acadia State Park, which provides an excellent place for hiking, boating, and fishing. The park goes right to the coastline, so you’ll be able to enjoy relaxing views while enjoying the rest of the park.

While in Bar Harbor, we recommend visiting the Abbe Museum, which highlights local and indigenous history. Abbe is part of the Smithsonian, so it is well done and curated.

Burlington, Vermont

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Burlington feels like a small town though the population is nearly 50,000. You should visit Church Street, which is for pedestrians only and offers some nice local shops and cafes.

One highlight of Burlington is – you guessed it – the waterfront. Burlington is well known for offering water sports from boating to water skiing. 

Afterward, head out for a drink, as Burlington has many craft breweries for a relaxing beer. 

You might know Burlington as the home of Ben and Jerry’s ice cream. Check out the factory and the hall of retired flavors that you won’t see in grocery stores anymore.

Green Mountain National Forest, Vermont

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This national forest is quite large and a great place to be, especially if you enjoy the outdoors and disconnecting for a bit. 

The park has plenty of wildlife, and you could catch a glimpse of beavers and moose while walking the trails – though it is safe, of course, there may be bears present.

Green Mountain also has a 140-foot waterfall. If that sounds like a rather tall waterfall – it is, and you should go see it.

Cape Cod, Massachusetts

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There are more than a few things to do in Cape Cod. 

The area is known in part for having the National Seashore, which is a national park created by the JFK administration with many miles of shoreline and many hiking and biking trails.

As an area with plenty of coastlines and harbor, you’ll be able to see lots of historic lighthouses that guided fishers and merchants home over the centuries.

Rhode Island shores

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We just call this Rhode Island shores because Rhode Island isn’t very big in itself – and because most of the trip is along the shoreline.

Starting from US 1, you can travel down the coast and have many beaches available to stop at.

When should I travel through New England


Most people who travel to the New England states suggest doing so in the fall because of the eye-popping foliage. 

The presence of brownstone and red brick homes really does add the visual presence of the northeast and is unmistakably beautiful. 

Fall is also fairly temperature in the area, and unless you are traveling from the deep south, probably won’t require much more than a jacket.


Vermont and New Hampshire, amongst other states, are quite well known for superb skiing resorts and winter activities. 

While the Atlantic and surrounding bays won’t exactly be swimmable, something about the northeastern forests in the winter are dramatically beautiful in their own way.


A New England summer is the best time to head to the coastline for water sports and the beaches. 

The area doesn’t get near as hot as parts of the south and Florida during the summer, making it pleasant for those who would prefer to avoid the peak of summer heat. You’ll also find lots of cities having the 4th of July and other summer celebrations.


Much like fall in New England, Spring brings a different variety of colors to the northeast, especially to the side roads. 

The first states won’t be overly hot from March to May, but you can still take a dip in a lake or the Atlantic.

New England Travel Tips

Avoid highways and main roads

We suggested a couple of particular highways take that brings you along the coast, but otherwise, the best parts of New England are on the side roads.

Part of the reason for this is that states like New York, Massachusetts, and Connecticut are as well known for their traffic jams as they are for their sightseeing offerings. 

Plus, taking the side roads is way more fun and bound to offer you views of old barns, scenery, and something that isn’t road signs and concrete.

Take your time

This could be said of any road trip – but take your time.

New England offers many things to discover that are both on the map and maybe a bit more spontaneous. Take a moment to soak in visuals and histories like covered bridges and old barns. 

Key Takeaways

  • Among the best places for road trips in New England are Boston and Cape Cod
  • Maine and New Hampshire also make for great stops with outdoor sports, seafood, lighthouses, and history
  • Many people make the trek to or around New England in the fall, when the trees are bursting with color
  • Another popular time is the winter, as many small towns are decorated for Christmas – and because skiing and snowboarding are quite popular.