Best Road Trips From Boston

Enjoy the freshest seafood in Maine, head for a museum and sightseeing tour to New York, enjoy a day under the sun at the beaches in Cape Cod or take the family to one of the world-famous theme parks in Orlando; the possibilities on a road trip from Boston are endless!

Top Road Trip Destinations From Boston

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Our rankings are based only on editorial opinion, not any commercial consideration.
The amazing Niagara Falls is renowned for its beauty and is the collective name for three waterfalls that straddle the international border between Canada and the USA.

πŸš— 470 miles ⏱️ 7 hours

No matter what time of the year you visit Niagara Falls, you will fall in love with its majestic scenery. If you travel during the warmer months, you can take a boat tour to see the raw power of nature up close.

Get ready to explore beautiful cities and landscapes in Upstate New York as you drive past Albany, Syracuse, Finger Lakes and Buffalo en route.

Times Square, New York at dusk

πŸš— 215 miles ⏱️ 4 hours

If one city has something unforgettable for every type of traveler, it is the Big Apple. Spend some time at Times Square, explore world-class museums, enjoy Broadway shows and visit the iconic landmarks.

This drive features a great mix or urban and natural, and you can visit places such as Wells State Park, Wadsworth Atheneum Museum of Art in Hartford and New Haven en route.

A wonderful morning in Portland, Maine, with the sea and Portland Head Light view at sunrise.

πŸš— 110 miles ⏱️ 1 hour, 50 minutes

Portland is a coastal gem known for its lighthouse-dotted landscapes. From strolling along the cobblestone streets of the Old Port to treating yourself to fresh seafood and craft beer, Portland is the quintessential New England town.

En route, you will find plenty of amazing new places to discover on the coast, such as Maudslay State Park, Portsmouth Market Square and the cute towns of York and Ogunquit.

Panoramic view of the stunning fall colors and blue waters of the Bay in Acadia National Park

πŸš— 320 miles ⏱️ 6 hours, 30 minutes

Acadia National Park is one of the most-visited parks in the country and it is easy to understand why. Hike granite peaks, bike historic carriage roads, and witness sunrise at Cadillac Mountain where the mountains meet the sea.

This drive is a feast for the eyes with endless coastal scenery in Portsmouth, York, Ogunquit and Portsmouth as well as a dip inland to visit the beautiful town of Augusta.

Washington DC, USA in spring season at the Tidal Basin and Jefferson Memorial.

πŸš— 440 miles ⏱️ 7 hours, 40 minutes

A visit to Washington DC, is a must for any history buff. Here, you can tick iconic landmarks off your bucket list, such as the Lincoln Memorial, the Smithsonian Museums, and the White House.

Some of the charming New England towns you can visit en route include Hartford and New Haven as well as iconic cities such as New York and Philadelphia.

Wooden bridge across lagoon to small island with vibrant sunset

πŸš— 120 miles ⏱️ 2 hours, 20 minutes

Cape Cod and Provincetown are amazing summer destinations. Known for its stunning beaches, historic lighthouses, and buzzing arts scene, this picturesque peninsula is also a great place to enjoy whale watching from mid-April to October.

You can expect some inspirational oceanside scenery on this drive, and visit Plymouth, Sagamore Beach, Nickerson State Park and Cape Cod National Seashore.

Liberty Bell old symbol of American freedom in Philadelphia Pennsylvania, USA

πŸš— 400 miles ⏱️ 7 hours, 10 minutes

If you have spent some time in the US, it is likely that you are familiar with the Liberty Bell and Independence Hall in Philadelphia. Come here for history, and you will end up staying for the eclectic neighborhoods and the famous Philly cheesesteak!

You will drive past a beautiful stretch of New England on this drive, and get to spend time at Providence and New Haven, followed by a quintessential visit to the Big Apple.

Skyling of Providence, Rhode Island from across the Providence River.

πŸš— 50 miles ⏱️ 1 hour

If you are looking for the perfect blend of historic charm and modern sophistication, Providence is the perfect destination from Boston. Make sure to enjoy a scenic walk around the WaterFire art installation.

Even though this is a relatively short drive, there is plenty to see en route, such as the Quincy Quarries Reservation, Blue Hills Reservation and the beautiful F. Gilbert Hills State Forest.

Frontenac Castle in Old Quebec City in the beautiful sunrise light.

πŸš— 390 miles ⏱️ 7 hours, 40 minutes

For a slice of Europe in North America, Quebec City is a UNESCO World Heritage site famous for its fortified colonial core and stunning ChΓ’teau Frontenac. Here, you will enjoy the French heritage of the city and its delicious cuisine.

This cross-border adventure will take you past Portsmouth, Portland and Augusta before you cross into Canada to visit Saint Georges before you reach your destination.

Toronto, Canada skyline with purple light and the city in the background reflecting in the water in the foreground.
10.

Toronto

πŸš— 600 miles ⏱️ 9 hours

Discover Toronto, Canada's largest city! From its easily recognizable CN Tower to its bustling markets, expansive green spaces, and waterfront districts, you will find plenty to do in this charming city.

Before you travel across the border into Canada, you can visit the New York State Capitol in Albany and Saratoga Springs, as well as Kingston and Oshawa once in Canada.

Millennium Park, Chicago, Illinois
11.

Chicago

πŸš— 985 miles ⏱️ 14 hours, 50 minutes

You will immediately recognize the famous Chicago skyline as you approach the Windy City, full of Midwest charm. Dive into the city's jazz and blues scene, savor deep-dish pizza, and visit iconic sites like Millennium Park.

En route you will drive through many iconic cities on this drive to Chicago, such as Albany, Syracuse and Cleveland as well as visit the Finger Lakes.

High rise buildings with sunlight hitting at an angle and red and yellow fall colours on the trees in the foreground
12.

Montreal

πŸš— 300 miles ⏱️ 4 hours, 45 minutes

A relatively manageable drive across the Canadian border and you will find yourself in Montreal, home to the historic streets of Old Montreal and Mount Royal Park, which features stunning views and snowshoeing and tubing in winter.

Driving north to Canada, you will get to visit Montpelier and Burlington in Vermont, which is particularly beautiful in the fall, before crossing the border.

Nova Scotia, Canada with coastline views from the Keltic Lodge in Ingonish on the Cabot Trail on Nova Scotia on a sunny day.

πŸš— 660 miles ⏱️ 14 hours, 30 minutes

Nova Scotia is located where the Atlantic Ocean meets rugged coastlines and jaw-droppingly beautiful landscapes. Another destination where you can admire historic lighthouses and indulge in fresh seafood.

This drive will take you past one coastal view after another such as in Portland, Bar Harbor and stunning Acadia National Park before you reach Canada.

Myrtle Beach in South Carolina at dusk with the city skyline and beach.

πŸš— 930 miles ⏱️ 17 hours, 10 minutes

Head to Myrtle Beach for a fun-filled getaway in the heart of the Grand Strand. Enjoy miles of sandy beaches, amusement parks, and live entertainment. This family-friendly destination offers something for everyone.

There are plenty of amazing places to visit on this route, such as New York, Philadelphia and Virginia Beach. You can also see the wild horses of Chincoteague National Wildlife Refuge.

Raleigh, North Carolina, USA downtown as viewed from the Capitol Building grounds.
15.

Raleigh

πŸš— 730 miles ⏱️ 12 hours, 20 minutes

Raleigh is the capital of North Carolina, known for its pretty parks, and historic sites. When in Raleigh, we recommend visiting the North Carolina Museum of Natural Sciences and strolling through the beautiful Pullen Park.

This drive is an urban adventurer's dream with New York, Baltimore and Washington DC directly en route. You can also make a detour to Richmond.

Longer road trips from Boston

Orlando, Florida, USA at Universal studios city walk with a view of the Lighthouse, entrance to Islands of Adventure.
1.

Orlando

πŸš— 1,400 miles ⏱️ 23 hours, 40 minutes

From the magic of Walt Disney World to the popular rides of Universal Studios, Orlando offers endless fun for families and visitors of all ages.

Miami, Florida, USA with a skyline view of the city, palm trees and sea in the foreground.
2.

Miami

πŸš— 1,580 miles ⏱️ 25 hours

Soak up the sun in Miami, famous for its stunning beaches, and glitzy nightlife. During the daytime, you can enjoy a tour to view the Art Deco buildings of South Beach.

Beautiful sunset of Los Angeles downtown skyline and palm trees

πŸš— 3,115 miles ⏱️ 48 hours

Famous for its iconic Hollywood Sign, always-busy Venice Beach, and glamorous Rodeo Drive, Los Angeles is one of the best destinations on the Pacific Coast.