7 Coolest Towns in New England for a Summer Vacation

New England's smaller coastal towns deliver their summer character through specific anchors: a beach with sand that actually squeaks, an 1857 stone lighthouse still working a major harbor entrance, an offshore island reachable only by mail boat, a Revolutionary War monument 306 feet tall. The seven below each run on something durable rather than the generic summer-getaway feel. Each one supports an afternoon or a long weekend without needing the marquee tourist destinations to fill the time.

Manchester-by-the-Sea, Massachusetts

Singing Beach is the local headliner, named for the squeaking sound the dry sand makes underfoot in summer. The phenomenon comes from the uniform size and silica content of the grains. The town sits on the North Shore of Massachusetts about 30 miles north of Boston along Cape Ann, with a working harbor and a downtown of mid-19th-century commercial buildings.

Masconomo Park sits along the harbor for low-key afternoons. The Coolidge Reservation on the eastern edge of town adds a 66-acre conservation property with ocean views from Bungalow Hill. The Manchester Historical Museum on Union Street keeps records on the town's 19th-century shipbuilding and cabinet-making history (Manchester cabinets earned a national reputation in the 1840s and 1850s). The 2016 Casey Affleck film of the same name was filmed here, though the town has settled back into its quieter summer rhythm in the years since.

Narragansett, Rhode Island

Point Judith Lighthouse has guarded the southern entrance to Narragansett Bay since 1810, replacing an earlier tower that was destroyed by the Great September Gale of 1815. The current 51-foot octagonal brick tower dates to 1857. The point marks the navigational divide between the bay and Block Island Sound, and the working Coast Guard station next door keeps the area operational.

The Central Street Historic District anchors the town's Gilded Age character with the surviving fabric of the old Narragansett Pier resort district, including the towering arched stone Towers (1883), the surviving McKim, Mead and White entrance to the long-vanished Narragansett Pier Casino that mostly burned in 1900. Scarborough State Beach handles the summer beach traffic with three-quarters of a mile of sand on the open Atlantic. The Narragansett Summer Concert Series runs free shows on Tuesday evenings at Veterans Memorial Park from late June through August.

Wells, Maine

Wells was settled in 1640 and incorporated in 1653, the third-oldest English town in Maine after Kittery and York. The Wells Reserve at Laudholm, a 2,250-acre research and education site managed under the National Estuarine Research Reserve System (a federal partnership with the National Oceanic and Atmospheric Administration), covers seven miles of trails through salt marsh, upland forest, and shoreline.

The Rachel Carson National Wildlife Refuge is headquartered in Wells and includes 11 separate units along the Maine coast, named for the marine biologist whose 1962 book Silent Spring launched the modern environmental movement. Wells Beach stretches just over two miles along the Atlantic, with the smaller Moody Beach picking up south of the Webhannet River estuary. Lobster shacks line Route 1 north through the town center.

Bennington, Vermont

The Bennington Battle Monument rises 306 feet, the tallest structure in Vermont, commemorating the August 16, 1777 Revolutionary War engagement that turned back a British raid on the colonial supply depot here. The battle (which actually took place a few miles west, in present-day Walloomsac, New York) is considered one of the turning points leading to the American victory at Saratoga two months later. An elevator runs to the observation level at 200 feet for views across Vermont, New York, and Massachusetts.

The Bennington Historic District covers the old village around the monument, with the First Congregational Church (1805) and the Old Burying Ground where Robert Frost is interred. Downtown Bennington, about three miles southeast, holds the Bennington Museum (one of the largest public collections of Grandma Moses paintings) and the Burt Henry Covered Bridge over the Walloomsac River.

Eastport, Maine

Eastport sits on Moose Island and holds the distinction of being the easternmost incorporated city in the United States, which gives it the first sunrise in the country most days of the year. The deepwater port runs about 65 feet at mean low tide, the deepest natural harbor on the East Coast, and handles the occasional commercial vessel too large for ports further south.

The Eastport Historic District covers a compact downtown of late-19th-century brick commercial buildings overlooking the harbor. The Tides Institute and Museum of Art works on contemporary art with a regional focus, and the Eastport Lighthouse on the breakwater dates to the 1830s in its original incarnation. The Eastport Pirate Festival runs the second weekend in September with a battle reenactment in the harbor, and the town's "Old Sow" whirlpool (the largest tidal whirlpool in the Western Hemisphere) churns off the southern tip of the island on a daily tide cycle.

Madison, Connecticut

Hammonasset Beach State Park occupies the southern edge of Madison with two miles of shoreline along Long Island Sound, the longest public beach in Connecticut. The Meigs Point Nature Center inside the park runs year-round programs covering the salt marsh, coastal forest, and tidal flats, with a touch tank of local marine species.

The Madison Green Historic District at the town center preserves the colonial layout around the First Congregational Church (1838). The Allis-Bushnell House on the green operates as the headquarters of the Madison Historical Society with rotating exhibits on the town's shipbuilding and farming history. Surf Club Beach handles the smaller town-park beach traffic on the east side of the harbor. R.J. Julia Booksellers on Boston Post Road is one of the strongest independent bookstores in New England.

Monhegan Island, Maine

Monhegan Island sits 12 miles offshore and can only be reached by mail boat or seasonal passenger ferry from Port Clyde, Boothbay Harbor, or New Harbor. There are no cars on the island, no paved roads, and roughly 75 year-round residents. The summer population swells to several hundred, including the artists who have made Monhegan a working colony since the 1880s, when Robert Henri, George Bellows, Edward Hopper, and Rockwell Kent all painted here.

The Monhegan Museum of Art and History occupies the keeper's quarters at the Monhegan Island Light, built in 1824 and automated in 1959. The 17 miles of hiking trails on the back side of the island lead to Cathedral Woods and the 150-foot cliffs at Whitehead and Blackhead. The Lupine Gallery and several working studios run open hours through the summer season. Day-trippers ride out, walk one or two of the trails, eat at the Monhegan House or the Island Inn, and ride back on the afternoon boat.

Coast and Inland, Mountains and Islands

The seven cover the geographic and stylistic spread of New England summer. Manchester-by-the-Sea has a beach with a particular geological quirk. Narragansett has working 19th-century lighthouse and resort architecture. Wells protects 13,000 acres of coastal habitat in the name of Rachel Carson. Bennington reaches 306 feet into the sky on a Revolutionary War monument. Eastport runs the deepest natural harbor on the East Coast. Madison hosts the longest public beach in Connecticut. Monhegan keeps its art colony running with the same materials it has used since the 1880s. The work of a summer trip is matching the place to what you actually want to do.