Kennebunkport, Maine

Kennebunkport has all the makings of a nostalgic Maine summer vacation, and in fall, you get much of the same experience with fewer people competing for it. The warm-weather rituals haven’t disappeared: You can still grab a lobster roll and fried clams from the beloved Clam Shack before spending the afternoon on Goose Rocks Beach. But fall brings its own reasons to visit. The surrounding landscape begins to turn, adding autumn color to coastal drives and walks, while the Seashore Trolley Museum’s Pumpkin Patch Trolley takes riders aboard a vintage trolley to pick out a pumpkin on select dates through Oct. 18. In Cape Porpoise, lobster boats come and go from the working harbor with Goat Island Light just offshore, while Dock Square is home to local shops and galleries set among historic buildings near the Kennebunk River. Save time for Ocean Avenue, too, where the road follows the rocky shoreline past some of Kennebunkport’s best-known oceanfront homes.

Where to Stay

A Kennebunkport staple since 1914, The Colony Hotel overlooks the Atlantic and Kennebunk River. Its 140 individually designed rooms span five buildings, from the historic Main Inn, which welcomes guests through late October, to the more contemporary Coveside rooms, which remain open year-round. The private beach is still a major perk come fall: Even if sunbathing is off the agenda, guests can head straight to the sand for a crisp morning walk along the water. The oceanfront Marine Room and Ocean Terrace serve elevated American fare with locally sourced ingredients—think local mussels, lobster eggs Benedict, and salsa made with Maine sweet corn—plus a generous breakfast buffet. Family-owned since 1947, The Colony comes with one more increasingly rare perk: no resort fee.

Chatham, Massachusetts

By fall, Chatham’s Main Street is no longer packed with peak-season crowds, but the shops, cafés, and local institutions that make it worth visiting remain. Don’t miss the two-story Where the Sidewalk Ends, part bookstore and part café, or Chatham Candy Manor, a local fixture known for hand-dipped chocolates and fudge made from a decades-old recipe. From downtown, head to Chatham Lighthouse, which has watched over this stretch of the Cape since the early 19th century, then cross the road to Lighthouse Beach for a walk along the barrier beach and views across the Atlantic. Come October, the town shifts into fall mode: Pumpkin People in the Park (Oct. 12–31) fills Kate Gould Park with elaborate displays created by local businesses and residents, while the annual Oktoberfest (Oct. 17) takes over downtown with live music, food, and seasonal festivities. It’s a chance to experience the Chatham people come for in summer—Main Street, the lighthouse, and long walks by the water—with a decidedly different backdrop.

Where to Stay

Set on 25 waterfront acres overlooking Chatham Harbor, Chatham Bars Inn has been welcoming guests for over a century. Accommodations include rooms in the historic Main Inn, The Cottage Collection—housed in separate cottage-style buildings around the property for added privacy—and 12 adults-only suites directly above the spa. The latter is a standout in its own right, with treatment rooms, steam rooms, saunas, and a relaxation pool. A wooden boardwalk leads to the resort’s quarter-mile private beach on Aunt Lydia’s Cove, where fall may be too cool for sunbathing but is prime time for a walk with views toward the Cape Cod National Seashore’s North Beach Island. Among the resort’s several restaurants and bars, STARS stands out for its harborfront dining room and elevated take on comfort food—Maine blueberry pancakes and French toast bread pudding at breakfast, lobster pasta at dinner—with Norman Rockwell’s Spirit of America hanging above the fireplace.

Newport, Rhode Island

Newport’s biggest draws were never dependent on beach weather, which makes fall an especially good time to explore the City by the Sea. Tour Gilded Age mansions like The Breakers and Marble House, then see some of those same sprawling estates from the 3.5-mile Cliff Walk, where the path runs alongside the Atlantic. Downtown, Thames Street cuts through the heart of Newport’s waterfront district, putting shops, restaurants, and historic wharves within walking distance. When the leaves begin to turn, take the long way around town via Ocean Drive, a 10-mile coastal route that passes Brenton Point State Park, Fort Adams, and some of Newport’s most dramatic stretches of shoreline. Then on Oct. 17 and 18, the Bowen’s Wharf Seafood Festival takes over the historic wharf with lobster rolls, chowder, oysters, stuffed quahogs, and live music. Newport has plenty to fill a fall weekend before you ever set foot on a beach.

Where to Stay

Wayfinder Newport brings a hip, design-forward feel to a city better known for Gilded Age grandeur. Its 197 rooms and suites pair coastal colors with custom furnishings, vintage finds, and work by local artists, while plush Matouk linens and Rhode Island-made Shore Soap Co. bath products add thoughtful local touches. Downstairs, the all-day Little Clam bar and restaurant draws guests in its own right, spotlighting Rhode Island farmers and fishermen in dishes like local oysters, New England clam chowder, and lobster rolls. While the hotel sits outside Newport’s historic downtown, round-trip shuttle service to Bowen’s Wharf makes it easy to reach Thames Street and the waterfront without worrying about parking. Back at the hotel, the outdoor party deck has games and plenty of room to hang out; there’s also a 24-hour fitness center, and pets are welcome.

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