FALL MIGHT REPRESENT a certain end to seasonal wanderlust — back to school, back to routine — but it shouldn’t mean you’re doomed to be landlocked until summer’s all-too-faraway return. Many New Englanders know that the autumn months are actually the best time to get out on the water — the ocean’s warm(ish) enough to be swimmable, the fish are plentiful, the seals are back, the tourists out of the way. Mornings and evenings may be a bit brisker than what you enjoyed back in July but, you know, that’s what fleece is for.
Hoisting Sails | Stonington, Connecticut
Many people overlook Stonington in favor of its more glorified neighbor, Mystic, and that’s a good part of “the borough’s” appeal. In fact, the historic harborside town — it’s the oldest Portuguese fishing village in the United States still in operation — has all the galleries and quaint shops, wine bars, and family-run restaurants as its next-door neighbor. At the nonprofit New England Science & Sailing (nessf.org, 860-535-9362), founder and lifelong sailor Spike Lobdell and his staff run sailing and hydrofoiling programs for adults and kids of all experience levels, including women-only tutorials, keelboat one-on-ones, lessons for adaptive athletes, and charters for those who prefer to just sit back and hoist glasses of champagne. The center also offers paddle board and kayak rentals and tours, and BYO sunset booze cruises through Stonington Harbor, well into the fall. Stay at the friendly 18-room Inn at Stonington (innatstonington.com, 860-535-2000), two doors down from the science and sailing center, where guests feel comfortable enough to wander down to breakfast in their pajamas. Take to your balcony to watch commercial fishing fleets return to the harbor with the local scallops, lobster, and bluefish you’ll find served up at favorite in-town spots like Noah’s Restaurant (noahsfinefood.com, 860-535-3925), which has been doing sea to table for nearly 40 years, and the newer Dog Watch Café (dogwatchcafe.com, 860-415-4510), whose dock hosts many a heated cornhole tournament.
Fishing for Striper | Block Island, Rhode Island
A trip to Block Island is a little like going back in time: Miles of old stone walls, vast expanses of land trust-preserved green space, and what locals endearingly call “island Wi-Fi” (hopefully your e-mail can wait). While the majority of lodgings have stayed true to the island’s Victorian-era roots — heavy on the four-poster beds and floral wallpaper — this year’s renovation of the former Surf Hotel brings the Block a more retro-modern alternative. Redone by New England-based boutique hotel group Lark Hotels, the new Block Island Beach House (blockislandbeachhouse.com, 401-466-5500) has 31 minimalist-chic rooms featuring original artwork, vintage surfboards, and Polaroid cameras to rent.
September and October offer some of the island’s best saltwater fishing, and Captain Chris Willi at Block Island Fishworks (sandypointco.com, 401-466-5392) will drag you out of bed at 4:30 a.m. for a fruitful morning of trolling Narragansett Bay for bluefish, striped bass, and the occasional fluke. Plenty of rocky outcroppings, such as Old Harbor Point, also offer the opportunity to spearfish. At night, celebrate your catch with water-view cocktails on the lawn of the Atlantic Inn (atlanticinn.com, 401-466-5883), followed by nachos topped with local tuna at Eli’s (elisblockisland.com, 401-466-5230) or Narragansett Bay mussels at the tucked-away Winfield’s (winfieldsbi.com, 401-466-5856).
Island Hopping | Casco Bay, Maine
As far as New England islands go, the Casco Bay Islands are something of a best-kept secret, despite being easily accessible all year by Fogg’s Boatworks water taxi (foggsboatwork.com, 207-415-8493) or Casco Bay Lines ferry (cascobaylines.com, 207-774-7871). Casco Bay Lines also offers a captain-narrated, very-Maine tour of the islands by mail boat; all leave from the terminal in downtown Portland. The closest and most populated of the six year-round islands is Peaks Island — just a 17-minute ferry ride from the mainland — where the new Island Lobster Company (islandlobsterco.com, 207-956-7488) boasts a trap-to-table menu of classic Maine fare: clams, scallops, crab, and, naturally, lobster, hauled in daily from the restaurant’s own boat. The restaurant also has rooms for rent via Airbnb (airbnb.com; search “rooms at Island Lobster Company”).
From Peaks, hop over to Great Diamond Island, where the Inn at Diamond Cove (innatdiamondcove.com, 207-805-9836) provides the perfect summer camp vibe — tennis courts, fire pit, a game room complete with old school bowling lanes and Ms. Pac-Man — from which to explore the island’s various coves on foot or by golf cart. At night, opt for dinner on the lawn at resident-favorite Diamond’s Edge Restaurant (diamondsedgerestaurantandmarina.com, 207-766-5850) or drinks on the porch at flamingo-themed newcomer Crown Jewel (crownjewelportland.com, 207-766-3000), whose rotating selection of house Collins cocktails and inventive takes on New England classics (see: baked oysters with yuzu pearls, steamers with chimichurri, lobster raviolo) have attracted droves of day trippers since its opening last summer.
The next day, borrow bikes from the inn and boat over to Chebeague Island for a sweaty, but scenic, 6-mile bike loop followed by lunch at the island’s Chebeague Island Inn (chebeagueislandinn.com, 207-846-5155). If you’re too tired to return, not a problem: You’ll find something to your liking among the inn’s 21 stylish rooms.
Biking on Water | Burlington, Vermont
This quintessential New England college town is part of the 1,600-mile long Lake Champlain Bikeways network, with bike routes that include a recently expanded and refurbished Island Line Trail circling the Lake Champlain waterfront and leading to a causeway running right through it — one of the only places you can ride your bike across the middle of a lake. At the causeway’s end, a family-run ferry takes bikers across a 200-foot gap in the trail to the island of South Hero, where the Accidental Farmer Café (617-852-2304), a 10-minute bike ride in, offers microgreens and burgers made with local grass-fed beef served out of a rigged-up Dodge van. The adjacent seventh generation apple orchard Allenholm Farm (allenholm.com, 802-372-5566) provides the perfect finish with maple creemees (basically, maple-flavored soft serve).
Stay at Burlington’s Hotel Vermont (hotelvt.com, 855-650-0080), which offers guests use of one of six custom-made Budnitz steel city bikes, or rent an electric model from North Star Sports (northstarsportsvt.com, 802-863-3832). Whether your ride is assisted or not, you’ll certainly earn a post-bike double IPA or two at waterfront brewery Foam Brewers (foambrewers.com, 802-399-2511), before sampling all the Turkish small plates at James Beard Award-nominated Honey Road (honeyroadrestaurant.com, 802-497-2145). Or carry out the water theme at Bleu Northeast Seafood (bleuvt.com, 802-864-8600), which pulls in fresh seafood daily and lays claim to the best lobster roll this side of the Vermont-New Hampshire border.
Oyster Harvesting | Duxbury, Massachusetts
These days, you can enjoy Island Creek oysters at any number of New England eateries, not to mention Per Se in New York City and Napa’s The French Laundry. But do you always have to be so fancy? Throughout the fall, Island Creek’s 11-acre farm and official headquarters offers would-be oystermen and women (also kids) working tours of its beds (islandcreekoysters.com, 781-934-2028). Board the 27-foot Carolina Skiff for a primer on aquaculture, hands-on oyster harvesting, and shucking and eating as you go (BYOB). If you don’t know how to shuck, you’ll quickly learn. Back on shore, a bayfront raw bar awaits to satisfy any lingering bivalve cravings, alongside heartier offerings that include caviar, tinned seafood boards, and chips and clam dip, plus local beer, cider, and wines by the bottle and glass to wash it all down. Ultra-enthusiasts can book a night in the Caretaker’s Cottage, open to the public this year for the first time.
Catching Waves | Rye, New Hampshire
The under-visited coastal town’s got some of the best surfing in New England, and a laid-back surfer vibe to match. Die-hards know that summer surfing is just a warm-up; fall and winter are when the waves get serious (but not scary). Through the fall, surf shop Summer Sessions (603-319-8207, newhampshiresurf.com) offers group lessons on mechanics, timing, and surfer etiquette — including its popular Ladies Night series for beginners and experienced alike — at Jenness State Beach, just across the street from the shop. Just bring yourself; they’ll provide the board and the wet suit. Afterward, saddle up to the old wooden bar at The Carriage House (carriagehouserye.com, 603-964-8251) for local littlenecks, a glass of rosé, and a welcoming vibe whether you’ve come dressed for date night or drag yourself in with a hoodie and saltwater hair. Overnight options in Rye are slim — just the way locals like it — but Portsmouth is only 10 minutes away. Book a room there at the intimate Ale House Inn (alehouseinn.com, 603-431-7760), a renovated 130-year-old brewery, or the grander Wentworth by the Sea in New Castle (wentworth.com, 603-422-7322), where massage therapists are on hand to work out any post-ride soreness.
Lobstering | Kennebunkport, Maine
Lobster in the summer is a given; in the fall, it’s a delight. During a 90-minute trip aboard the Kennebunkport-based Rugosa, a classic Downeast-style wooden lobster boat (rugosalobstertours.com, 207-468-4095), you’ll tour the Kennebunk River, hauling traps, rubber-banding the (angry) catch, and learning more about lobster mating rituals than you likely ever thought possible. You won’t get any to take home with you but that’s perfectly fine: You can get your fill of lobster all around town, starting with the lobster omelets at Salt and Honey (thesaltandhoney.com, 207-204-0195), and moving on to lobster tacos and lobster spring rolls at The Boathouse restaurant (boathouseme.com, 207-967-8223), before ending with the butter-poached lobster at Ocean at the Cape Arundel Inn and Resort (capearundelinn.com, 855-346-5700). The inn, a modern restoration of an 1895-era home, is Kennebunkport’s only oceanfront hotel and restaurant, with most rooms sporting views of the crashing surf along Ocean Avenue, as well as of the Bush compound, the former first family’s summer retreat. And while you won’t find lobster ice cream in this town — that’s more a Bar Harbor thing, some three and a half hours north — flavors like the Persian Love Cake, Nutella Cranberry, and Goat Cheese with Whiskey and Figs Compote at Rococo (rococoicecream.com, 207-835-1049) likely won’t leave you missing it one bit.
Whale Watching and Stalking Seals | Newburyport, Massachusetts
In spring and fall, Plum Island Kayak (plumislandkayak.com, 978-462-5510) runs group and private seal paddles along the brackish Merrimack River. Spot harbor and gray seals — most of them bigger than many bears in New England — sunning themselves along the rocky coast before they head south for the winter. Despite the temptation, keep your distance: They may look cute enough to pet, but they will bite, and they’re protected under federal law.
Whale watching, meanwhile, is at its prime in the fall, and Newburyport Whale Watch runs four-hour weekly outings into the open ocean, led by a pair of marine naturalists (newburyportwhalewatch.com, 800-848-1111). Bird enthusiasts on either type of voyage will also appreciate the chance to see ospreys, sandpipers, cormorants, and the occasional bald eagle. You could, in fact, spend the entire weekend here and never venture to land, thanks to a new fleet of houseboats for rent in Newburyport Harbor and Hilton marinas (houseboatsatnewburyport.com, 888-755-1472). But, then again, you have to eat. Hit up Brine (brineoyster.com, 978-358-8479) for buck-a-shuck oysters, Sea Level for steamers (sealevelnewburyport.com, 978-462-8862) and lobster rolls two ways. Visit the expansive new location of the Black Cow (blackcowrestaurants.com, 978-499-8811), anchored by a 28-foot-tall sailboat mast that runs up through the restaurant’s three floors, for surprisingly solid sushi. As carnivores and kids will tell you, the best burger in town is at Lexie’s (peaceloveburgers.com, 603-815-4181).
Ocean Racing and Drinking in the View | Newport, Rhode Island
A regular stop on the professional racing circuit, Newport is arguably the country’s epicenter of high-performance sailing, and each of the retired 12-meter class racing yachts at 12 Meter Charters — Columbia, Heritage, and Onawa — come with stories of hard-won victories and close-call defeats (12metercharters.com, 401-851-1216). Get a feel for what it’s like to compete in the America’s Cup with the three-hour racing experience, which pits two of the boats against one another in a simulated regatta. Participation is entirely optional; you’re more than welcome to just sit back and hold on. Spend the night at The Cliffside Inn (thecliffsideinn.com, 401-847-1811), recently refurbished under new ownership and just steps from the 3.5-mile Cliff Walk — one of New England’s most stunning oceanfront paths — or the waterfront Gurney’s (gurneysresorts.com, 401-849-2600), which recently unveiled bilevel suites. Plenty of area restaurants offer post-sail ocean views, but the one to beat is from the rooftop of the Vanderbilt Hotel (aubergeresorts.com/vanderbilt, 401-846-6200), which serves up a stunning sunset, a stiff Negroni, and blankets for when it gets just a little too fall-like. Sit back and enjoy the autumn twilight as it sets over Newport Harbor; winter, after all, will be here before you know it.