14 Best Road Trips From Boston, USA (2024 Guide)

From relaxing in a Cape Cod coastal town to hiking the rocky coastline of Maine, explore the best of New England on these road trips from Boston!

Boston is one of the most famous cities in the United States. With a well-known colonial history, world-class sports teams, and loads of entertainment and dining options, Boston is a vibrant and beautiful city.

One of the best things to do while visiting the Boston area is try a road trip or two! Boston is surrounded by quintessential New England scenery that wows locals and visitors alike.

So if you don’t already have a car, rent one and get exploring!

You can road trip up to New Hampshire, Vermont, or Maine. Taste fresh lobsters, hike in the lush mountains, swim in a pristine lake, or just enjoy a scenic drive through multicolored fall foliage.

Or head south to Rhode Island or Cape Cod. Amazing beaches, charming coastal towns, and offshore islands await.

Those with more time to spare can even try a road trip outside of New England. Drive down to New York City, the city that never sleeps. Or road trip to the famous Niagara Falls, or head north to check out Canadian gems like Montreal and Quebec.

Boston road trips are an amazing way to explore the northeast USA. Whether you’re looking for a weekend getaway or a quick day trip, these fantastic places near Boston are perfect for a road trip!

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars, which has the largest range of vehicles for the best value on the market.

When is the best time of year for road trips from Boston?

New England offers something special at all times of year, so you can do a road trip from Boston year round.

However, each season is different and you may want to plan your road trips to suit the weather.

Summer in New England is hot and rich with greenery. This is the best time to road trip north to Maine, New Hampshire, Vermont, or Canada. You’ll have ideal conditions for outdoor activities like hiking, golfing, swimming, and sightseeing in nature.

The summer months are also the most crowded at touristy spots near Boston. So the ideal time for road trips is autumn or late spring.

Autumn around Boston is famously gorgeous. The leaves change and turn the forests into magical kaleidoscopes of color. The temperatures also start to get cooler and crowds may lessen as people go back to school and work, which may be better for hitting the hiking trails.

Spring also has pleasant weather, though the weather is more unpredictable. Spring in the Boston area can sometimes still feel like winter, and snowstorms sometimes appear as late as May!

And of course, winter is freezing and harder for road trips from Boston. Snow and ice may cause some road closures. However, winter is still beautiful, and you can do some fun road trips to the mountains for skiing or snowboarding.

Just make sure you have a good vehicle and some recovery gear in case of rough road conditions. Always check local weather alerts before your road trips as well!

Best Road Trips From Boston

Let’s dive into the best road trips from Boston! These road trip destinations showcase the best of New England and the surrounding areas. Each road trip leads to a popular destination, whether it be a city, coastal town, national park, natural attraction, or a general region.

The driving times and distances from Boston reflect the direct route from downtown Boston to the destination. You can modify any road trip to be longer and stop at nearby attractions along the way.

So after a few days of exploring Boston, grab your rental car and get ready to explore the beauty, culture, history, and nature of northeast USA!

1. Acadia National Park, Maine

• Distance from Boston: 280 miles
• Driving time: 4.5 hours

Acadia National Park is the only national park in New England, and it is a real treat to explore. Full of granite peaks, dense woodlands, rich biodiversity, and picturesque shorelines, this is a nature lover’s paradise.

Visitors can hike Cadillac Mountain, the highest point on the US East Coast that offers incredible sunrises. Other popular hiking trails include the challenging Precipice Trail or Beehive Trail, or the easy Jordan Pond Path or Ocean Path Trail.

The road trip from Boston to Acadia National Park takes you north along the New Hampshire and Maine coastlines. Stop in charming coastal towns like Portsmouth, York, Kennebunkport, and Portland along the way if you want a more leisurely road trip.

Bar Harbor is a popular place to stop before or after exploring Acadia National Park as well. The town is often considered the gateway to the national park, and it’s a great place to spend the night during your road trip.

Nestled between the sapphire waters of Frenchman Bay and the forests of Acadia, Bar Harbor is a picturesque place to go whale watching, kayaking, and exploring. Check out the town’s historic streets lined with unique shops, art galleries, and seafood restaurants.

Book a self guided audio tour of Bar Harbor and Acadia National Park to make your road trip even easier!

2. Cape Cod, Massachusetts

• Distance from Boston: Between 60 and 115 miles, depending on where you go
• Driving time: Between 1-2 hours

Another one of the most popular road trips from Boston is Cape Cod.

This iconic peninsula lined with sand bars, coastal marshes, and quaint towns is a popular holiday and retirement spot for New England locals. If you’re looking for the perfect summer road trip from Boston, Cape Cod is a great choice!

The entire peninsula is packed with adorable towns and idyllic beaches. From Bourne and Sandwich at the top of Cape Cod to Provincetown and the Cape Cod National Seashore at the end, you can spend days driving around Cape Cod and never tiring of the scenery and attractions.

Go bicycling along the Cape Cod Rail Trail, snap a picture of a historic lighthouse, or visit attractions like the Cape Cod Museum of Natural History and the Wellfleet Bay Wildlife Sanctuary.

You could spend a few days road-tripping along the entire peninsula and stopping in popular towns along the way such as Falmouth, Mashpee, Barnstable, Yarmouth, Chatham, and Eastham.

Cape Cod is a popular weekend trip from Boston, so try to go during the week if you want to escape the crowds! It’s also a road trip that is best completed in summer. Cape Cod’s beaches are still beautiful in the dead of winter, but lots of local establishments close when summer ends so you’re options are more limited.

3. Martha’s Vineyard, Massachusetts

• Distance from Boston: 93 miles
• Driving time: 2.5 hours

Martha’s Vineyard, along with other New England islands like Block Island, Plum Island, and Nantucket, are like little slices of paradise on the chilly Atlantic Coast.

Because they are islands, any of these road trips would require a ferry ride. Martha’s Vineyard is one of the most popular island trips to take from Boston. Simply drive down to Falmouth or Woods Hole in Cape Cod and get the ferry over.

Once you arrive, spend some time exploring the historic houses of Oak Bluffs, the elegant streets of Edgartown, and the beauty of Aquinnah’s clay cliffs.

Martha’s Vineyard also features a vibrant arts scene, exquisite dining options with a focus on fresh seafood, and numerous outdoor activities such as biking, hiking, and sailing.

You don’t necessarily need a car to explore islands like Nantucket and Martha’s Vineyard, but it does provide more flexibility on your trip. Check the ferry schedules online and book your ticket in advance to ensure it doesn’t sell out. Or if you’re just taking the ferry over for a few hours to explore on foot, you can buy your ferry ticket when you arrive at the terminal.

4. Stowe, Vermont

• Distance from Boston: 200 miles
• Driving time: 3.5 hours

One of the best road trips from Boston in winter is to Stowe, Vermont. This is a beautiful road trip year round, but Stowe is especially popular in wintertime for skiing and snowboarding.

Plus, driving through the remote forests and towns of Massachusetts and Vermont is magical in winter when the region is blanketed in fresh snow.

Once you arrive in Stowe, spend a few days enjoying this town in the north of the Green Mountains.

Stowe is near Vermont’s tallest mountain, Mount Mansfield, which offers exceptional skiing and snowboarding in the winter. Visit Stowe Mountain Ski Resort, the most popular ski resort in the area, to try winter sports on Mount Mansfield or Spruce Peak.

During the warmer months, the area transforms into a haven for hiking, biking, and camping. The charming downtown area of Stowe is filled with boutique shops, art galleries, and a variety of dining options.

5. Montreal, Canada

• Distance from Boston: 307 miles
• Driving time: 5 hours

Southeast Canada is actually one of the best road trip destinations near Boston! A road trip to Montreal will take you through New Hampshire and Vermont until you cross the border into Canada. Make sure you have your passport for this road trip!

Stowe, Vermont is slightly on the way to Montreal so you could combine the two destinations into a longer road trip. If you are hoping to make some stops on the way to Montreal, you’ll also be passing through two state capitals: Concord, New Hampshire and Montpelier, Vermont.

But there is obviously so much to do in the famous city of Montreal, so make sure you have at least a few days here!

Montreal is the largest city in the Canadian province of Quebec and is known for its old-world European charm.

Make sure you check out the historic Old Montreal with its cobblestone streets and Gothic Revival architecture. Plateau Mont-Royal is another popular neighborhood, with its bohemian vibe and colorful murals. Or join a St. Lawrence river cruise and enjoy the city from the water!

Montreal hosts numerous festivals throughout the year, including the world-famous Montreal International Jazz Festival. But the city is stunning year round, so definitely consider this road trip if you have time!

6. Newport, Rhode Island

• Distance from Boston: 71 miles
• Driving time: 1 hour and 20 minutes

A popular day trip destination from Boston, Newport is one of the most scenic places in Rhode Island.

Known for its opulent Gilded Age mansions, stunning waterfront views, and rich maritime history, Newport combines upscale elegance with coastal charm.

Often called the “Sailing Capital of the World,” Newport’s harbor is filled with yachts and sailboats, and the waterfront is fun to walk around even if you’re not into sailing.

Visitors can explore the historic Newport Mansions, such as The Breakers and Marble House, which showcase the grandeur of America’s wealthiest families during the late 19th century.

The Cliff Walk, a scenic 3.5-mile pathway along the eastern shore, offers breathtaking views of the Atlantic Ocean and the cool Newport architecture. Newport is also packed with cool shops, historic streets, and amazing restaurants with fresh seafood.

This is one of the shortest road trips from Boston as it’s only about an hour to reach Newport from downtown. So if you’re looking for a fun day trip that doesn’t require too much travel, this is a great option.

If you’re hoping to extend the road trip, you could even catch the ferry to Block Island and spend a day being a beach bum!

7. White Mountains, New Hampshire

• Distance from Boston: 165 miles
• Driving time: 2 hours and 45 minutes

A road trip itinerary through the White Mountains is stunning, especially in autumn. Those who love nature and foliage should add this weekend getaway from Boston to their bucket lists!

The White Mountain National Forest is packed with sloping hills, granite cliffs, towering mountains, lush forests, small towns, and New England charm.

Travellers flock here in autumn to witness the magnificent changing of leaves, but summer is also a fabulous time to explore the mountains. Hiking, camping, and backpacking are popular ways to adventure through the wilderness in the White Mountain National Forest.

There are lots of amazing hiking trails here, including the tallest peak in New Hampshire, Mount Washington. Other spectacular hikes include Flume Gorge, the Franconia Ridge Loop, and the famous Appalachian Trail.

If you’re not looking to hike, experience some small town charm in places like Lincoln or North Conway. The White Mountains make a gorgeous day trip, weekend getaway, or extended road trip from Boston.

8. Portland, Maine

• Distance from Boston: 112 miles
• Driving time: 1 hour and 45 minutes

As one of the most beloved cities in the Eastern United States, Portland showcases the best of New England culture and the scenery of the Maine coast.

See iconic coastal landmarks like the Portland Head Lighthouse, browse through galleries at the Portland Museum of Art, or sample local craft beers at the Allagash Brewing Company.

Stroll through the historic Old Port district and check out the quaint cobblestone streets, trendy shops, street art, and local eateries where you can get a fresh lobster roll.

Go for a nature walk or bike ride along the scenic Eastern Promenade, or go on a boat cruise through Casco Bay to admire the surrounding islands and waterways.

Whether you want to absorb natural beauty, laid-back culture, or New England history, Portland has it all. And it’s one of the best road trips from Boston to Maine!

9. New York City, New York

• Distance from Boston: 215 miles
• Driving time: 3 hours and 40 minutes

New York City is one of the most popular road trips from Boston, though this one is more about the destination than the journey. Driving from Boston to NYC is mainly highways that aren’t super scenic.

You can stop in small Massachusetts or Connecticut towns along the way. But most people just take the most direct route because it’s easier. You can get from Boston to New York City in under 4 hours and have ample time to explore the famous Big Apple!

Try to complete this road trip early in the morning or later in the evening to avoid peak traffic times going into the city. You probably won’t be able to avoid all traffic in NYC, but just have some good tunes for the car to keep you entertained along the way.

Once you arrive in New York City, you are absolutely spoilt for choice when it comes to activities and attractions.

NYC is home to some of the most famous sights in the world, from the Brooklyn Bridge and Empire State Building, to Times Square and Central Park. A CityPASS can help you save money on the top museums and attractions, which is amazing because city life in NYC is not cheap!

10. Lake Champlain, Vermont

• Distance from Boston: 216 miles
• Driving time: 3 hours and 35 minutes

Located about 3 and a half hours northwest of Boston, Lake Champlain is the sixth largest freshwater lake in the United States.

The lake spans over 120 miles in length and stretches into northern Vermont, New York, and Quebec, Canada. You could drive to any of the towns surrounding the massive lake, but one of the most convenient lakeside towns to reach from Boston is Burlington, Vermont.

Burlington is a small town with a big energy. There are festivals, museums, markets, and lots of entertainment, dining, and accommodation options in Burlington.

The town is also the perfect gateway to Lake Champlain, especially in the summer when water sports are enjoyable.

Visitors to Lake Champlain can enjoy boating, fishing, kayaking, canoeing, and swimming, with numerous beaches and marinas along its shoreline.

The Lake Champlain Islands, accessible by causeways and ferries, provide a tranquil retreat with scenic vistas, orchards, and opportunities for cycling and exploring local farms. This is an amazing road trip from Boston for those craving outdoor adventure!

View the best accommodations in Burlington, Vermont on Booking.com!

11. Niagara Falls, New York

• Distance from Boston: 467 miles
• Driving time: 7 hours

One of the more ambitious road trips from Boston is Niagara Falls. But the journey is worth it if you’ve never seen this natural wonder of the world before!

A direct drive from Boston to Niagara Falls is around 7 hours. You could quickly complete the drive in one day, or take your time and make some stops along the way.

This road trip will take you through western Massachusetts where you could stop in towns like Amherst or Springfield. Or you can stop in some popular New York destinations like Albany, Syracuse, and Buffalo.

But make sure you leave ample time to explore Niagara Falls, one of the world’s most famous waterfalls!

The falls consist of three major waterfalls: the Horseshoe Falls on the Canadian side and the American Falls and Bridal Veil Falls on the US side. Maid of the Mist is the most popular boat tour on the US side where you can tour the majestic falls from the water and get up close to the cascades.

Beyond the falls themselves, the surrounding Niagara Falls State Park offers hiking trails, gardens, and stunning views of the Niagara River Gorge, making Niagara Falls a truly unforgettable destination.

12. Providence, Rhode Island

• Distance from Boston: 50 miles
• Driving time: 1 hour

About an hour south of Boston lies Providence, another one of the best cities to explore in Rhode Island.

Providence is one of the oldest cities in the United States and has an abundance of cultural richness, historical landmarks, and a vibrant arts scene.

Visitors can stroll along the lively waterfront of the Providence River, indulge in the nightlife downtown, visit a local museum, or join a ghost tour to learn about the history in a unique way.

Families can check out the diverse animal exhibits at Roger Williams Park Zoo. History enthusiasts can tour the Rhode Island State House and Benefit Street, known as “The Mile of History,” featuring well-preserved colonial homes and museums.

Art lovers will appreciate visiting the Rhode Island School of Design Museum (RISD Museum), showcasing an extensive collection of art ranging from ancient to contemporary works.

Though it’s just a short drive from Boston to Providence, it’s a convenient road trip where you can get to know a very special city in New England!

13. Philadelphia, Pennsylvania

• Distance from Boston: 311 miles
• Driving time: 5 hours

Venture southwest from Boston through Connecticut, New York, New Jersey, and Pennsylvania to explore the city of Philadelphia. This is an easy city to visit after NYC as well if you want to combine the two into one road trip.

As one of the oldest cities in the United States, Philadelphia is full of things to do! The city is known for its colonial heritage, evident in iconic landmarks like Independence Hall and the Liberty Bell.

The city’s cobblestone streets in the historic district of Old City transport visitors back in time, offering a glimpse into the past through preserved colonial-era buildings and museums such as the Museum of the American Revolution.

Beyond its history, Philadelphia is a vibrant cultural hub, home to world-class art institutions like the Philadelphia Museum of Art, with its famous “Rocky Steps,” and the Barnes Foundation, housing an impressive collection of impressionist and modern art.

Philadelphia’s food scene is as diverse as its culture. The city’s Reading Terminal Market, a bustling food hall since 1893, is the best place to try local food including a famous Philly cheesesteak.

You don’t want to rush your exploration of Philly. So if you have a few days to spare, Philadelphia is one of the best road trips from Boston!

Check out this 3 Days in Philadelphia Itinerary for more ideas!

14. Quebec City, Canada

• Distance from Boston: 397 miles
• Driving time: 6 hours and 30 minutes

At about 6 and a half hours from Boston, Quebec City is an ambitious but worthwhile road trip destination. You could even combine this with a trip to Montreal, as the two Canadian cities are only about 260km apart.

Both cities are absolutely worth visiting if you want to experience the wonders of eastern Canada.

Quebec City in particular is a destination rich with history and culture. Start in the historic Old Quebec, a UNESCO World Heritage Site. The charming district is full of narrow cobblestone streets, 17th-century architecture, and the iconic Château Frontenac overlooking the St. Lawrence River.

Visitors can explore historic sites such as the Citadel, stroll along the scenic Dufferin Terrace, and immerse themselves in Quebec’s French Canadian culture through its museums, art galleries, and lively festivals like the Quebec Winter Carnival.

If you have time to venture beyond the city, you can explore Quebec’s natural beauty in the Laurentian Mountains. Extend your road trip through the scenic Laurentian and Appalachian roads and try outdoor activities such as skiing, hiking, ice skating, and wildlife watching.

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