13 Road Trip Ideas (And Must-Visit Pit Stops) From Boston

Best road trip ideas from Boston

Calling all road trippers! If you’re searching for an exciting destination to look forward to on your next journey from Boston, look no further than these alluring Northeast cities. 

Best Road Trip Ideas From Boston

There’s nothing like the great American road trip. Trading wings for wheels gives you the freedom to explore off-the-beaten-path destinations at your own pace, and helps keep vacation costs down. And the best part? When you’re ready to escape the hustle and bustle of downtown Boston, you’ll find much of the Northeast is right at your fingertips!

Consider booking a vacation home on FlipKey and save even more during your getaway. Whether you choose a secluded cabin, cozy beach cottage, or an urban apartment, rentals provide extra space to stretch your legs and all of the comforts of home, including a full kitchen, free laundry, and wireless Internet.

From the breezy beaches of the Jersey Shore to classic New England vacation spots like Portland, we’ve mapped out 13 great road trips from Boston. So hop in the car, hit the road, and explore the ribbons of highway that wind through the region.

Plymouth, Massachusetts (40 mi, <1hr)

Drive down to Plymouth from Boston.

Revel in American history and discover where the Pilgrims first landed almost 400 years ago: Plymouth. Visitors from near and far flock to this gorgeous seaside destination to see landmarks like Plymouth Rock and the Mayflower II, a replica of the ship the Pilgrims sailed. Had your fill of history? Drink a Cape Codder cocktail while admiring Cape Cod Bay from the back deck of your rental or lounge on the sprawling, sandy beaches.

Our Top Restaurant Pick: CabbyShack

Our Top Activity Pick: Jenney House Museum

See all Plymouth vacation rentals on FlipKey!

Rockport, Massachusetts (45 mi, <1hr)

Rockport is located approximately 25 miles northeast of Boston at the tip of the Cape Ann peninsula.

If you’re searching for a road trip from Boston that won’t leave you cramped in the car for hours, Rockport is an ideal choice. Located on the rocky jut of land known as Cape Ann, this coastal town boasts award-winning dining and attractions, without the congestion of a big city. Sit in the sand as the waves wash over the shore, or hike along Halibut Point. Rockport is the picture of tranquility!

Our Top Restaurant Pick: My Place by the Sea

Our Top Activity Pick: Rockport Music

See all Rockport vacation rentals on FlipKey!

Hampton, New Hampshire (50 mi, 1 hr)

Book a rental in Hampton, NH.

Within an hour’s drive of Boston, Hampton is an easily accessible destination just over the Massachusetts-New Hampshire border. Here, succulent seafood, eclectic shops, and picturesque beaches abound, and you’ll never run out of things to do! Take a dip in the ocean at Hampton’s eponymous beach, watch sand sculptors in action, or fly a kite high above the dunes—the area is bursting with possibilities.

Our Top Restaurant Pick: The Goat

Our Top Activity Pick: Cinnamon Rainbows Surf Co.

See all Hampton vacation rentals on FlipKey!

Providence, Rhode Island (50 mi, 1 hr)

Find your rental in Providence, RI.

A blend of historic sites, modern attractions, and big city conveniences make Providence worth a stop on your next road trip from Boston. Fill your days in the “Renaissance City” feeding giraffes at the Roger Williams Park Zoo, exploring the ins and outs of Brown University’s campus, or sipping an espresso in the historic Federal Hill neighborhood, also known as Little Italy. At sunset, hop aboard an authentic Venetian gondola for a romantic cruise down the Providence River.

Our Top Restaurant Pick: GraciesProv

Our Top Activity Pick: RISD Museum

See all Providence vacation rentals on FlipKey!

Ogunquit, Maine (75 mi, 1.5 hrs)

Drive up to Ogunquit, Maine from Boston, Massachusetts.

For easy access to beautiful Maine beaches and a bustling town center, follow New England’s spectacular coastline up to Ogunquit. Sandwiched between the Atlantic Ocean and the Ogunquit River, there are endless opportunities for outdoor recreation. Set sail from Perkins Cove, climb Mount Agamenticus, or wander along Marginal Way, a scenic cliff walk that spans more than a mile. With fresh seafood, sheltered beaches, unique art galleries, and vacation homes for every budget, Ogunquit is the idyllic road trip destination from Boston.

Our Top Restaurant Pick: Northern Union

Our Top Activity Pick: Ogunquit Museum of American Art

See all Ogunquit vacation rentals on FlipKey!

Kennebunkport, Maine (90 mi, <2 hrs)

Coastline in Kennebunkport, Maine

This quintessential New England destination, nestled along the coast of southern Maine just 90 miles north of Boston, is best known for its fine white sand beaches, quaint historic districts, and remarkable art galleries. Enjoy the sea with a whale watch or charter a boat for a unique perspective of the local lighthouses. Prefer dry land? Bike, walk, or drive down scenic Ocean Avenue for jaw-dropping views and a glimpse of former President George Bush’s summer home.

Our Top Restaurant Pick: Bandaloop

Our Top Activity Pick: Seashore Trolley Museum

See all Kennebunkport vacation rentals on FlipKey!

Old Orchard Beach, Maine (100 mi, <2 hrs)

Visit the beach in Maine.

Just 30 minutes up the road from Kennebunkport, Old Orchard Beach sits along a 7-mile stretch of golden sand. Bask in the sun at the city’s namesake, Old Orchard Beach, or plan a day of family-friendly fun at Palace Playland, the only beachfront amusement park in New England. In the afternoon, cool off with an ice cream cone at the pier, or kick back on your rental’s balcony overlooking the water.

Our Top Restaurant PickJoseph’s by the Sea

Our Top Activity PickPalace Playland Amusement Park

See all Old Orchard Beach vacation rentals on FlipKey!

Saco, Maine (100 mi, <2 hrs)

Views in Saco, ME.

Take your pick of outdoor activities in this small town on the southern coast of Maine. There’s the Eastern Trail that winds through the woods of Maine, zip-lining adventures at Monkey Trunks, and fishing charters on the Atlantic. If you’ve got kids in tow, head to Funtown Splashtown to cool off without the hassle of loading the car with beach gear. Consider a vacation home near Saco Bay with a BBQ grill, beach views, and plenty of space to make your trip extra special!

Our Top Restaurant Pick: The Run of the Mill Public House and Brewery

Our Top Activity Pick: Funtown Splashtown

See all Saco vacation rentals on FlipKey!

Portland, Maine (110 mi, 2 hrs)

Find a rental in Portland, Maine

Known for its luscious lobster rolls, picturesque shoreline, and historic charm, Portland is a haven for vacationers in New England. At just two hours from Boston, it’s a convenient destination to get to, too. Stroll along the brick sidewalks, sip on a pint at a local brewery, or play skipper for a day exploring the open waters by boat. Spend a long weekend in Portland and you’ll leave Vacationland—Maine’s official slogan—feeling positively refreshed.

Our Top Restaurant Pick: Duckfat

Our Top Activity Pick: Children’s Museum & Theatre of Maine

See all Portland vacation rentals on FlipKey!

Provincetown, Massachusetts (115 mi, 2.5 hrs)

Rent Provincetown vacation rentals

Gorgeous beaches, charming lighthouses, unique art galleries, and an exuberant town center—there’s only one Provincetown. Situated at the very tip of Cape Cod just two and a half hours from Boston, this scenic spot is a popular road trip destination for those looking to escape the city. Head to Commercial Street for shopping and dining, or even book a beautiful, historic home right on this main drag. Prefer some fun in the sun? Visit the beaches of the Cape Cod National Seashore—almost three quarters of Provincetown is preserved as a part of this park.

Our Top Restaurant Pick: Strangers & Saints

Our Top Activity Pick: Art’s Dune Tours

See all Provincetown vacation rentals on FlipKey!

Killington, Vermont (160 mi, 3 hrs)

Road trip ideas from Boston

Described by travelers as “an awesome mountain retreat!”, Killington boasts four seasons of non-stop adventure. Situated in the Green Mountains, Killington has some of the highest and most varied mountain terrain in the region. From hiking and biking during the summer to skiing and snowshoeing in the winter, the area’s natural beauty will steal your breath away. With FlipKey, you can stay near Killington Resort to be near all of the action, or find yourself in a country house off the beaten path. Wherever you choose, nothing beats a trip to this woodsy Vermont destination 160 miles northwest of Boston.

Our Top Restaurant Pick: PastaPot

Our Top Activity Pick: New Life Hiking Spa

See all Killington vacation rentals on FlipKey!

Lake George, New York (225 mi, 4 hrs)

Road trip ideas from Boston

This 32-mile long “Queen of American Lakes” offers lots of activities, perfect for stretching your legs after a long car ride. Navigate the trails at Prospect Mountain, hit the links at Top of the World Golf Resort, or go parasailing over Lake George, legs dangling freely in the air. Rent a cozy cottage right on the lake for ultimate convenience, or choose an away-from-it-all log home for total relaxation. Whichever you pick, you’re sure to enjoy a weekend of outdoor recreation in New York’s scenic Adirondack region.

Our Top Restaurant Pick: Bistro LeRoux

Our Top Activity Pick: Parasailing Adventures

See all Lake George vacation rentals on FlipKey!

Jersey Shore, New Jersey (295 mi, 5 hrs)

Rent a beach home along the Jersey Shore.

No matter which beach town or seaside village along the Jersey Shore you make home, New Jersey’s sweeping coastline is well worth the car journey. The region spans from Sandy Hook in the north to Cape May Point in the south, with about 140 miles of sandy beaches and swaying dunes in between. Want to win big in Atlantic City? No problem! Dreaming of warm waters and ocean breezes? It’s all here! Jersey Shore has something for everyone.

Our Top Restaurant Pick: The Shrimp Box

Our Top Activity Pick: Naval Air Station Wildwood Aviation Museum

See all Jersey Shore vacation rentals on FlipKey!

Top Road Trip Destinations from Boston

  • Plymouth, Massachusetts
  • Rockport, Massachusetts
  • Hampton, New Hampshire
  • Providence, Rhode Island
  • Ogunquit, Maine
  • Kennebunkport, Maine
  • Old Orchard Beach, Maine
  • Saco, Maine
  • Portland, Maine
  • Provincetown, Massachusetts
  • Killington, Vermont
  • Lake George, New York
  • Jersey Shore, New Jersey