The Perfect New England Road Trip & Boston Flights from $98 🍁 🚗

The New England region is comprised of six states in the northeastern part of the US. Vermont, New Hampshire, Maine, Massachusetts, Connecticut, and Rhode Island. With beautiful differing landscapes and the total area combined being a quarter of the size of Texas, New England is the perfect place to plan your next road trip! Below we've compiled the near-perfect route to take when planning a visit.

For fall foliage, we recommend visiting in late September or early October to catch the leaves at peak color.

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Full-Service Flights to Boston

*The following flights are through full-service airlines like Delta, American, and JetBlue

Stop 1 Boston, MA

Fly into Boston Logan Airport and start your stay off by exploring this historical city. Take a walk along the freedom trail where Paul Revere made his famous ride back in 1775, visit Quincy Market for delicious food, and explore so much more of what this city has to offer.

Stop 2 Salem, MA

25 miles from Boston

Salem, Massachusetts is a port city most famously known for its witch trials that took place during the time of the Puritans. This city surely feels like magic and has many museums, shops, cafes, and the waterfront to explore. When visiting during the month of October make sure to prepare yourself for the crowds. This location is a top Halloween spot.

While in Massachusetts and driving North, you can explore more of the coastline and make visits to Newburyport, Plum Island, and Rockport just to name a few great locations.

Stop 3 Portsmouth, NH

44 miles from Salem, MA

Portsmouth, New Hampshire is another beautiful port city with many great shops, restaurants, and museums. Make sure to stop and check out the Strawbery Banke Museum—a historical immersive outdoor exhibition that takes you back in time.

Stop 4 Portland, ME

52 miles from Portsmouth, NH

Explore the seacoast of Maine and venture up to the city of Portland. While there, you should definitely try some Maine lobster and explore the Old Port waterfront. In the summertime, nearby Old Orchard Beach is a great location to lie out in the sun and enjoy the ocean waves.

If you have more time to spend in Maine, you should consider driving further up the coastline and making stops in Bath (35 miles from Portland), Boothbay Harbor (24 miles from Bath), Bar Harbor (116 miles from Boothbay), and of course, Acadia National Park (Right next to Bar Harbor).

Stop 5 North Conway, NH

62 miles from Portland, ME

Next stop is in the White Mountains. North Conway is a popular tourist spot at the base and has many great shops and ski resorts. Take the famous Cog Railway up Mount Washington, the tallest mountain on the East Coast. Drive through and hike among Crawford or Pinkham Notch. Watch out for Moose though, they are known for popping out of the surrounding wooded areas.

Stop 6 Burlington, VT

144 miles from North Conway, NH

First and foremost, on your way to Burlington, you must stop in the town of Waterbury and visit the Ben and Jerry's factory. After that, explore downtown Burlington and walk through Church Street—a great shopping district. Make sure to also check out Lake Champlain which is the sixth-largest lake in the US.

Stop 7 Providence, RI

264 miles from Burlington, VT

Providence Rhode Island is a great spot to add to your trip. Walk through trendy Thayer's Street and explore along the river bank by boat or foot. You should also visit the indoor botanical center in Roger Williams Park.

Stop 8 Cape Cod, MA

73 miles from Providence, RI

No New England road trip would be complete without visiting the Cape. Or one of the nearby islands; Nantucket and Martha's Vineyard. All three coastal locations are perfect for spending your summer.

Stop 9 Back to Boston

70 miles from Cape Cod, MA

Now we take you back to where the trip began, bustling Boston!

Additional Information

*All of our deals are available at the time of publishing, but prices are subject to fluctuate and change at any time.