Monday, October 24, 2016
Updated : May 27
- Published : May 18

15 picturesque New England towns for your next road trip

We've laid out your most Insta-worthy trip through the Northeast.


As summer approaches, sleepy towns across New England are beginning to wake up from hibernation. With flowers in bloom and leafy trees covering the mountains, summer is without doubt the best season to visit New England — and the only time to enjoy its pristine beaches.

The region has plenty to offer outside of major cities like Boston and Providence, especially on the coast, where locals flock to relax on the beach, go biking and sailing, and enjoy the delicious seafood New England is known for. Starting in Connecticut and heading north to Maine, here are 15 of the most scenic News England destinations to visit for summer fun, food, history and culture. —Laura Itzkowitz

Rhode Island

Gilded Age tycoons flocked to the charming seaside city of Newport to build their summer "cottages" at the turn of the century. Early examples of these homes—such as Isaac Bell's shingled house—actually resemble cottages. With the arrival of the Vanderbilts came opulent mansions modeled on European palaces. The Breakers, designed by Richard Morris Hunt in the Italian Renaissance style, is the grandest, though Marble House, modeled on Le Petit Trianon at Versailles, set the tone for the rest. Though the mansions are Newport's claim to fame, there's plenty to do in this historic city.

Insider Tip: Every July, the Newport Music Festival puts on performances by world-class musicians at the mansions.

RELATED: 15 best family-friendly resorts for summer vacations


Halfway between New York City and Boston, Mystic has plenty of coastal attractions. The historic town is home to Mystic Seaport, the world's largest maritime museum with over 500 vessels, including the last remaining whale ship in the world. At the Mystic Aquarium, you can see New England's only beluga whales, plus penguins, seals, sea lions, and plenty of other aquatic animals. Embrace the kitschy side of town at the Olde Mistick Village, where you'll find souvenirs and homemade fudge at Franklin's General Store.

Insider Tip: Check out the spots featured in the 1988 movie Mystic Pizza that made Julia Roberts famous.


Home to the Tanglewood music festival, Lenox exudes mountain charm unique to the Berkshires. Winding roads twist and turn, enveloped by verdant canopies that open onto spectacular views of the rolling valleys dotted by farmhouses. The main attraction in Lenox is The Mount, Edith Wharton's country estate. Built in 1902, Wharton designed the home based on the precepts outlined in her 1897 book, The Decoration of Houses, which emphasized simplicity and harmony. Three acres of formal gardens complement the home, providing a beautiful backdrop for a stroll.

Insider Tip: When in the Berkshires, a visit to MASS MoCA—the contemporary art museum in a complex of 19th-century factory buildings—is a must.


If you're planning a getaway to Cape Cod, Hyannis is a great place to start. The Kennedy clan certainly thought so; they vacationed here often and JFK gave his 1960 victory speech at the Hyannis Armory. The John F. Kennedy Hyannis Museum in Old Town Hall commemorates his time there. With a large concentration of shops, restaurants, and hotels, Hyannis is the Cape's commercial hub. It is also home to the Cape Cod Potato Chips Factory.

Insider Tip: Cape traffic is notoriously bad in the summer. Avoid driving to the Cape on Friday afternoons, when Bostonians leaving the office head to summer homes for the weekend.

RELATED: 10 great city walks


Known as an affluent summer colony, the population of Martha's Vineyard swells to five times its normal size from June until Labor Day. It's easy to see why: the Vineyard's pristine beaches and calm waters are ideal for relaxing. Originally settled by the Wampanoag people, the island's natural beauty has been preserved at the Aquinnah Cliffs, which are protected as part of the Wampanoag Reservation land. Together with his son, Thomas Mayhew, who bought the island from English "owners" in 1641, maintained good relations with the Native Americans living there.

Insider Tip: Today you're more likely to see celebrities than Native Americans. The Obamas have been vacationing on Martha's Vineyard since 2009 and are planning to return this summer.


Smaller in size and population than Martha's Vineyard, the island of Nantucket maintains its quaint historic character thanks to strict building codes introduced in the 1950s. The island saw its heyday in the 1800s, when it was the most important whaling port in the world. Back then, merchants docked their ships in the harbor and unloaded barrels of whale oil, which was once used to make candles. You can still imagine them carting barrels through the cobblestone streets. The entire town is a National Historic District and an idyllic vacation destination.

Insider Tip: Learn about Nantucket's whaling history firsthand at the Whaling Museum.


About an hour north of Boston on Cape Ann, Gloucester is the country's oldest seaport and predates Boston and Salem. It was established as an English settlement in 1623, and today you can visit historic houses like the Cape Ann Museum. Gloucester's scenic beauty has attracted many artists, including Winslow Homer, William Morris Hunt, Mark Rothko, Maurice Prendergast, and Edward Hopper. The Rocky Neck Art Colony—the first settled artist colony in the U.S.—has many contemporary artist studios and galleries.

Insider Tip: Don't miss Beauport, the Sleeper-McCann House, which was the lavish summer home of one of America's first interior designers.

RELATED: 25 things to do in New York City this summer


Near Gloucester, Newburyport was a major shipbuilding center and retains some of New England's finest Federal-period homes. The town boasts the oldest continuously operating courthouse in the U.S., and was a stop on the Underground Railroad. A statue of prominent abolitionist William Lloyd Garrison stands on the site where he held abolitionist meetings in Brown Square. The First Presbyterian Church, built in 1756, features a clock bell tower, cast by Paul Revere.

Insider Tip: Strolling through the center of town, you'll find plenty of antique shops and charming restaurants.

For the rest of the best New England towns for your next road trip, like taking in the rugged coastal beauty of Bar Harbor, visit Fodor's.

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