Hamptons in the offseason: An insider's guide
Shop for produce and flowers or grab a coffee at Amber Waves in Amagansett. Credit: Amber Waves
Ask an insider and they’ll tell you fall is the best time to visit the Hamptons.
"I love the way the sun comes through the trees, the angle of light in September," says Andrea Ackerman, an associate broker at Brown Harris Stevens in Bridgehampton who's been a full-time East End resident for over four decades. "The fields change from green potato plants to brown to the cover crop. It’s beautiful." And more affordable, she adds, referring to the local retail scene. "There are always great sales in September because the level of activity has decreased."
Along the near-20-mile stretch between Southampton and Amagansett, you’ll find apples to pick, beaches to stroll, museums to visit and drinks to enjoy. Get an early start and take in the best of the area on a fall day. Here are some go-to stops on and off Route 27.
Grab breakfast and window shop in Southampton
Stop by Shippy's in Southampton for breakfast. Credit: Linsey Kromer
Cross the Shinnecock Canal and grab breakfast in Southampton at Shippy’s (36 Windmill Lane, 631-283-0007, shippys.com), a lively local hangout since 1954 that has been recently renovated. Find a hearty platter of potato pancakes, bratwurst and eggs in honor of its German roots, as well as more contemporary fare including granola and avocado toast. If the weather is nice, grab a coffee and a cinnamon swirl scone to go from the original Tate’s Bakeshop (43 N. Sea Rd., 631-283-9830, tatesbakeshop.com) and head to Coopers Beach (268 Meadow Lane), which landed the No. 2 spot on Dr. Beach’s Best Beaches of 2024 list, for a morning walk.
Sisters Tanya Willock and Temidra Willock-Morsch co-own Hidden Gem in Southampton. Credit: Gordon M. Grant; Tanya K. Willock
Before heading out of town, peek into a few independent shops. Hidden Gem (47B Jobs Lane, 631-259-3494, hiddengemny.com), the brainchild of design-forward sisters Tanya Willock and Temidra Willock-Morsch, displays some of the owners’ Caribbean-in-the-Hamptons flair, with a curated selection of home goods, clothing and accessories.
Head to the farms in Bridgehampton and Water Mill
Spookley's children's maze is one of three corn mazes to explore at Hank's Pumpkintown in Water Mill. Credit: Newsday/Beth Whitehouse
Heading toward Bridgehampton, the choices are aplenty for picking or picked local apples. You can’t miss Hank’s PumpkinTown (240 Montauk Hwy., Water Mill, 631-726-4667, hankspumpkintown.com), with its big red barn store, pick-your-own orchard, fall-themed play structures and pedal cart racetrack.
Bags of apples are sold at Milk Pail in Water Mill. Credit: Gordon M. Grant
Farther down Route 27 is the Milk Pail (1366 Montauk Hwy., Water Mill, 631-537-2565, milk-pail.com). The stand is run by the Halsey family, farmers in the area since 1640. It showcases a constantly changing selection of apple varieties from the family orchards. Along with your apples and cider, you may not be able to resist grabbing a few cider doughnuts, which are deposited near the checkout counter.
Shop for flowers, produce and pies at Fairview Farm in Bridgehampton. Credit: Gordon M. Grant
Off the highway, Fairview Farm ( 69 Horsemill Lane, Bridgehampton, 631-537-6154) offers freshly baked pies and an 8-acre corn maze.
Have lunch and explore museums in Bridgehampton
The Bridgehampton gallery space showcases women makers and artists. Credit: Women's Art Center of the Hamptons
Emerge from the orchard in time for a bit of culture before lunch. Bridgehampton boasts the new Women’s Art Center of the Hamptons (2418 Main St., 631-899-4253, wachamptonsny.org), with gallery space for showcasing women makers.
A peppermint and mint chocolate chip cone from the Bridgehampton Candy Kitchen in Bridgehampton. Credit: Gordon M. Grant
Two restaurants in town are especially good for people-watching afterward. Grab a booth at Bridgehampton Candy Kitchen (2391 Montauk Hwy., 631-537-9885) for a cheeseburger deluxe with fries and a shake. Fitting for an eatery open since 1925, Candy Kitchen is cash only. Another Bridgehampton favorite, Bobby Van’s (2393 Montauk Hwy., 631-537-0590, bobbyvansbridgehampton.com) also specializes in comfort food — Reuben sandwiches, Cobb salads and steak frites — and features a lively bar and floor-to-ceiling, street-facing windows.
Hit the beach or enjoy a cocktail in Sagaponack and Wainscott
A boardwalk leads to the ocean at Sagg Main Beach, the Southampton Town beach, in Sagaponack. Credit: Heather Walsh
Sagg Main Beach (315 Sagg Main Rd., Sagaponack) has a roomy parking lot with no permit necessary. You can walk for miles along the shoreline.
Jon Rose, a retiree from Amagansett who devotes his fall to fishing, recommends keeping an eye out for the striped bass migration from September through December. "If you are lucky enough to be on the beach when the fish are very close, which is all the time during the fall, you’ll see something incredible. Areas up to two or three acres across of fish exploding on the surface, jumping in the air," he says. No fishing rod? Rose advises keeping a cooler in the car and stopping at The Seafood Shop (356 Montauk Hwy., Wainscott, 631-537-0633, theseafoodshop.com) for the local catch.
People sit on the outside patio next to the vineyard for tastings at Wolffer Estate Vineyard in Sagaponack. Credit: Gordon M. Grant
Warm up with an adult beverage at Sagaponack Farm Distillery’s (369 Sagg Rd., Sagaponack, 631-537-7300, sagaponackfarmdistillery.com) rustic-chic tasting room where you can sample vodka made from 100% Sagaponack-grown potatoes and wheat. If grapes are of more interest, the château next door, Wölffer Estate Vineyard (139 Sagg Rd., Sagaponack, 631-537-5106, wolffer.com), offers glasses and flights of Long Island merlot, Cabernet Franc, Chardonnay, and sauvignon blanc as well as cider, cheese and charcuterie.
Get a Hamptons history lesson in East Hampton
East Hampton’s Main Street is architecturally rich. Download the East Hampton Historical Society’s walking tour (easthamptonhistory.org) to learn about more than two-dozen significant structures that collectively tell the story of the area.
The Hook Windmill on the green in East Hampton. Built by Nathaniel Dominy V, a prominent East Hampton craftsman, it is one of 11 surviving 18th and early 19th century wind-powered gristmills on Long Island. Credit: Gordon M. Grant
A few notable buildings: The Hook Windmill (a mill that served the village has existed on this site since 1736, and the current mill dates to 1806), the Lyman Beecher House (home to Harriet Beecher Stowe’s preacher father), and Guild Hall (a museum, performing arts and education center; 158 Main St., 631-324-0806, guildhall.org).
End your day in Amagansett or Sag Harbor
Continue east to Amagansett. Stop by Amber Waves (367 Main St., Amagansett, 631-267-5664, amberwavesfarm.org), where Amanda Merrow and Katie Baldwin grow vegetables, fruits, grains and flowers. Take home some of the bounties of their fall harvest, or pick up preserves, pasta sauces, pickles and granola made in their farm kitchen. Proceeds support Amber Waves’ mission to teach local children about sustainable farming and to donate thousands of pounds of produce to local food pantries.
The tacos at Rosie's on a corn tortilla filled with summer slaw, house hot sauce and choice of pork, chicken, fish or veggies. Credit: Pauline White; Paul Niccolls
Visitors can catch a show at Stephen Talkhouse (161 Main St., Amagansett, 631-267-3117, stephentalkhouse.com) throughout the year. Or browse and buy old and new vinyl as well as cassette tapes and turntables at Innersleeve Records (199 Main St., Amagansett, 631-604-6248). Enjoy an early dinner at casual, friendly, farm-to-table Rosie’s (195 Main St., Amagansett, 631-604-5095, rosiesamagansett.com), where small appetites will be satisfied with salmon tartare and tortilla chips. At the same time, the ravenous can indulge in a 12-ounce rib-eye with roasted potatoes.
Toys and gifts on display at The Wharf Shop in Sag Harbor. Credit: The Wharf Shop
Alternatively, head west on Route 114 and end the day in Sag Harbor. A soaring space for the exhibition of world-class art, The Church (48 Madison St., Sag Harbor, 631-919-5342, thechurchsagharbor.org) is also a concert venue and community classroom, hosting dance parties and writing workshops throughout the year. In a constantly changing retail landscape, there are a handful of independent shops here that have stood the test of time. Find knitting needles, jam jars, contact paper and birthday candles at the Sag Harbor Variety Store (114 Main St., Sag Harbor, sagharborvariety.com). The Wharf Shop (69 Main St., Sag Harbor, 631-725-0420, wharfshop.com) has been delighting kids with toys, craft kits, stuffed animals and dollhouse furniture for more than 50 years. Sylvester & Company (103 Main St., Sag Harbor, 631-725-5012, sylvesterandco.com), Sag Harbor’s general store since 1989, sells art books, kitchen knives, leather bags and upscale pet supplies. Grab a cup of its famous cold brew coffee to go.
David Liszanckie, of Shelter Island, with Charlotte Moore, her son Robert, 3, and their dog Ramona, inside the tasting room at Kidd Squid Brewing Co. in Sag Harbor. Credit: Randee Daddona
Raise a glass to this vibrant town at Kidd Squid Brewing Co. (11 Spring St., Sag Harbor, 631-500-0522, kiddsquid.com), a tasting room in the old railroad station featuring 16-ounce drafts of the farm brewery’s lagers, IPAs and pilsners along with local wines, spirits and nonalcoholic beverages. Or celebrate the end of your day with sake and sushi at another Sag Harbor standby, Sen (23 Main St., 631-725-1774, senrestaurant.com), where diners wait patiently on the sidewalk for tables in the summer but walk right in as the days get shorter.
A previous version of this story misstated Fairview Farm's address. It is located at 69 Horsemill Lane, Bridgehampton and does not offer apple picking.