5 Seaside Escapes


Ask a native New Englander, and they’re likely to admit that locals often live up to the stereotype: pragmatic, reserved and forthright. But spend a little time in a New England town, and you’ll find a community bound by a shared respect for tradition, a love for the surrounding landscape and an uncommon attachment to the four seasons. Nowhere is this truer than along the coast. With some 6,130 miles of shoreline between Connecticut and Maine, visitors and locals alike share in the same appreciation for the sea. Whether you prefer a day sail to Block Island or beach time on Nantucket’s North Shore, you’ll discover even the smallest coastal town has its own distinct character and unique delights.

Experience quintessential New England with a visit to one or more of these quaint towns and beaches.

1. Westerly, RI

Photo by Hideaway Report editor

Drive 20 minutes in a northeasterly direction from Stonington Village to arrive in the town of Westerly, Rhode Island—the official starting point of coastal New England. (Technically speaking, New Hampshire has more coastline than Connecticut. The latter state’s shores belong to Long Island Sound, and are considered “tidal” rather than “coastal.”) The high summer season throughout the region generally runs from Memorial Day through Labor Day, but unless you’re the hale and hearty type, July and August are the preferred months for swimming.

As elsewhere in New England, a “town” is made up of a number of small villages. There’s Downtown Westerly (the municipal seat) and 12 other distinct communities that make up the Town of Westerly. According to Candice Traskos of Ocean House in Watch Hill, this area of Rhode Island is one of coastal New England’s best-kept secrets. Visitors “love the ‘Hamptons feel’ without the chaos and crowds. Our beaches are some of the best in New England, and there is a lot to do around town.” When is the best time to visit? “July and August are a lot of fun on the beach,” says Traskos, but it’s a busy time, so she prefers the quieter atmosphere in September. However, “a walk on the beach in the winter after it has snowed is incredibly peaceful. Someone should visit at least once a season to see the many faces of our area.”

Insider Tips

Beach Time: Head to Weekapaug Beach for family time, East Beach in Watch Hill for swimming and Napatree Point for a long walk by the dunes.

Scenic Drives: Roll along Ocean Drive in Watch Hill and Wawaloam Drive in Weekapaug.

Family Attractions: The Flying Horse Carousel in Watch Hill is the only surviving carousel of its kind in the U.S. The lucky child who pulls the golden ring gets a free ride.

In the Arts: Stroll the Virtu Art Festival in Wilcox Park in downtown Westerly on Memorial Day weekend. Take in free live music in Watch Hill every Tuesday through July and August.

Nearby: Visit the Mystic Seaport Museum in Mystic, CT, for nautical history, the Connecticut Wine Trail (for the obvious) and the Stonington Borough for a quintessential New England village experience.

2. Newport, RI

Photo courtesy of Castle Hill Inn

An hour’s drive up and over to Aquidneck Island, and you’ve arrived in Newport. The area has beaches, yes, but it is best known for its Gilded Age mansions along Bellevue Avenue. According to Margaret Wilcox at Castle Hill Inn, “The prevalence of historic architecture makes the simple act of walking down the street both educational and beautiful.” When you’ve toured the mansions and strolled Broadway, make your way over to the eastern side of Aquidneck. “There you can start your day with a hike around Sachuest Point National Wildlife Refuge, then refuel at Sweet Berry Farm, a local farm-market offering a casual farm café. Cap off the day with a tour and winetasting at Newport Vineyard,” says Wilcox.

Insider Tips

Beach Time: Spend the day at Easton’s Beach, rent a surfboard and cool down with a Del’s frozen lemonade.

Good Eats: Order The Mooring’s “bag of doughnuts,” a collection of lobster, shrimp and crab fritters.

On Foot: Sign up for a guided walking tour at The Museum of Newport History at the Brick Market and, of course, don’t miss the 3.5-mile Cliff Walk.

Scenic Drives: Make the “Ten-Mile Drive” from the southern end of the island past the mansions on Bellevue.

On the Water: Take a sailing lesson at Fort Adams with local outfitter Sail Newport.

When It Rains: Explore the Newport Art Museum or the International Tennis Hall of Fame.

Like a Local: Stroll Broadway, sample the beer selection at Pour Judgement, and try the Thai shrimp nachos at Malt.

On Your First Visit: Don’t miss the Breakers, the most elaborate of the Preservation Society mansions.

Upon Return: Visit the Isaac Bell House, a shingle-style home built in 1883.

Day Trip: Take the high-speed ferry from Newport to Block Island and tour the island by bicycle or moped.

3. Nantucket, MA

Hackleford Photography/iStock/Thinkstock

If you’re looking for more island time, head east to Nantucket by high-speed ferry or one of the seven airlines that service the island. At 14 miles long and 3.5 miles wide, Nantucket has more than 80 miles of coastline, but classic beaches are just a part of its appeal. The island’s historic character can be found in the cobblestone streets and cedar-shingle houses of Nantucket Town. “Due to the lack of heavy commercialism, Nantucket is not a place where you will find tourist traps,” says Bridgette Hynes of the Wauwinet and White Elephant properties. “One of the great benefits of visiting a small town like Nantucket is that locals and tourists share the same space and enjoy the same activities, restaurants and sights.”

Insider Tips

Beach Time: Head to Jetties or Steps Beach for family time, Fisherman’s or Surfside for the waves, and Madaket or ’Sconset (Siasconset) for a walking excursion.

Festivals for All Seasons: Discover the Daffodil Festival in April, the wine festival in May, the film festival and book festival in June and the arts festival in October. In December, Santa arrives for the Christmas Stroll courtesy of the U.S. Coast Guard.

Listen Live: Check out a Boston Pops concert at Jetties Beach.

When It Rains: Pay a visit to the Nantucket Whaling Museum.

Scenic Drives: Take Milestone Road past the island’s iconic moors, through quaint ’Sconset overlooking the Atlantic, then return to town via Polpis Road.

Upon Return: Visit during the fall, when the mild weather offers an ideal time for biking and walking while you take in the seasonal colors.

4. Chatham, MA


Due north of Nantucket lies Chatham, one of 15 towns on Cape Cod and perhaps its most beautiful, according to Mark Novota of Wequassett Resort and Golf Club. “The most popular destinations on the Cape include Chatham, Hyannis and Provincetown,” says Novota. “All have their own distinct charm. Chatham has always been my favorite,” he says. Galleries, boutiques and restaurants line Main Street, and visitors can enjoy regular concerts in the gazebo during the summer months. “Generations of families return to the Cape year after year to appreciate the seashore and simple family values,” says Novota. “It’s quintessential Americana.”

Insider Tips

Beach Time: Adventure to the Outer Beach, accessible only by boat, or check out Lighthouse or Hardings beaches. Nearby Coast Guard Beach in Eastham is considered one of the top 10 in the nation.

Good Eats: Sample the seafood at the Impudent Oyster, Chatham Squire and Delmar Bistro.

Look Out: Visit the Chatham Lighthouse, established by President Thomas Jefferson in 1808 to protect the ships circling the Cape.

Listen Live: Pull up a seat for the annual Cape Cod Jazz Festival in July.

Day Trip: Take the ferry to Martha’s Vineyard or Nantucket.

By Bike: Ride out on the eight-mile Chatham bike path past the lighthouse, the Chatham Fish Pier and the stately mansions and quaint cottages along the seashore.

5. Kennebunkport, ME


Contrary to popular belief, not all of the Maine shoreline is rocky. Many of the beaches in the southern part of the state offer sandy shores. “Goose Rocks Beach is one of the best beaches in Maine, and quite possibly in all of New England,” says Justin Grimes of Hidden Pond. “It’s protected by two small islands that shelter the bay and make it especially great for swimming.” In case you think it’s too cold, Al Black of The White Barn Inn says water temperatures are typically pleasant from late June through early September. Plus, you get two-for-one in Kennebunkport: From the coast, drive a mere mile inland and you’re in the thick of the forest. “I think it’s impossible to see everything Maine has to offer,” says Grimes. “Anyone that tells you they have isn’t telling the truth.”

Insider Tips

Beach Time: Swim Goose Rocks or Kennebunk Beach, and stroll Gooches, Middle and Mothers.

Good Eats: Sample the fish and chips at The Ramp and no-frills lobster and steamers at Langsford Road Lobster & Fish House.

Like a Local: Take a tipple at Federal Jack’s tavern or Old Vines Wine Bar.

On the Water: Test your sea legs aboard a classic wooden lobster boat with Rugosa Lobster Tours.

When It Rains: Visit the Seashore Trolley Museum or the nearby Ogunquit Museum of American Art.

Scenic Drives: Drive along Ocean Avenue to St. Ann’s seaside chapel, built in 1887, and on to Cape Arundel and Walkers Point.

Upon Return: Explore the oft-overlooked towns of Harpswell and Belfast, as well as Cheague Island.

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This article is an excerpt from the April, May, June 2016 edition of Traveler magazine. Click here to access the full issue.
By Hideaway Report Staff