New England Road Trips That Make You Fall in Love With the East Coast

How to Plan a Road Trip


As you can probably gauge, California's endless road trip destinations make it a very special place to live. So when I moved to New York City, I found myself craving the freedom and fun of a road trip. Not quite sure where to go, I worked with Pack Up + Go and rented a red Mustang convertible to plan a road trip that would prove this side of the country has just as many dreamy road trip destinations as my home state. While I'll always be partial to California's magnificent landscape, I ended up falling in love with New England while exploring it by car. So if you find yourself on the East Coast and want to plan a New England road trip, consider checking out these quaint, picturesque towns.

Mystic, Connecticut

Summer Road Trip Destinations
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Mystic, Connecticut is full of happy surprises. Wander down the main road to idyllic summer scenes like ice cream shops, sailboats on the harbor, and a certain pizza shop made famous by Julia Roberts in Mystic Pizza. Then head up the side street for some of the best oysters, lobster rolls, and views New England has to offer at Tree House. You could also try its finer dining option downstairs.

While you're in town, be sure to visit the famous Mystic Aquarium to experience beluga whales, sea lions, and more. 

Newport, Rhode Island

Underrated Summer Road Trip Destinations

Newport, Rhode Island, is a truly fascinating place. Design lovers and history buffs will have a blast touring the Gilded Age mansions, which were summer homes for wealthy American families like the Vanderbilts. And if it's a nice day outside, go drive along Cliff's Walk and then catch some rays at one of the many beaches. Oh, and you should definitely eat dinner at the oldest tavern in the U.S.: White Horse Tavern. 

Portsmouth, New Hampshire

New England Road Trip Destinations
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Portsmouth is just a 60-mile drive from Boston, making it super accessible if you're looking for a quick mini road trip. Though it's much closer than some of the charming seaside towns in Maine, it definitely has a similar feel (if you do want to travel further up the coast, we love Kennebunkport, Bar Harbor, and Camden, Maine). It's also the third oldest city in the U.S., boasting a lovely seaport and idyllic summer vibe. 

Plymouth, Massachusetts

New England Destinations

Part of the New England allure is the changing seasons and all the activities that come and go with them, especially for a California kid like myself. There's also the rich, palpable sense of history. Plymouth, Massachusetts, is one of those places, as it was the site of the first Pilgrim settlement. It's also home to beautiful, sprawling cranberry bogs, U-pick apple farms, and more. 

Harwich, Massachusetts

East Coast Road Trips
Lauren Stephanie Wells

Harwich is another town on Cape Cod with quintessential New England charm, and it isn't quite as far out there as Provincetown. Like many of the charming summer towns lining the cape, Harwich retains much of that colonial-era charm, though it's also home to some chic hotels, eateries, and shops now. It's the best of the old and new world in one place. 

Woodstock, Vermont

New England Road Trips
Lauren Stephanie Wells

Woodstock, Vermont, is where pumpkin spice dreams come to retire and go to heaven. While it may conjure up images of the British countryside, it almost feels more like you've stepped inside a time machine and landed in the 19th century. Rustic wooden fences, historic bridges, roaming sheep, and rolling hills abound.

Lake Winnipesaukee, New Hampshire

New England Road Trip Itinerary

Lake Winnipesaukee is the perfect destination if you want to head away from the coast to a lakeside retreat surrounded by trees and mountains. Once you arrive, there's not much to do besides chill out by the lake or get active with hiking and water sports like sailing, waterskiing, and wakeboarding. In the cooler months, it'll be the perfect cozy retreat.

Marlow, New Hampshire

Best New England Towns

With a population of 720, this quiet town is a welcome change to the fast-paced city life. Marlow, New Hampshire is an agricultural village, making it one of the most beautiful places to soak in the gorgeous fall foliage with nothing but peace and quiet to keep you company. 

Narragansett, Rhode Island

New England Road Trip Ideas
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Just across the way from Newport is the smaller town of Narragansett, Rhode Island. It truly is the ideal vacation town for travelers seeking a picture-perfect experience on a New England locale. You'll find streets neatly lined with shingled widow's walks, hydrangea bushes, open Jeeps, and the occasional lighthouse. You'll want to keep your cameras nearby everywhere you go.

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