Fall might be the most underrated season in the Hamptons. With the summer heat and crowds out of the way, it’s easier to linger outside a bit longer and celebrate everything from a crisp beer to a harvest party to a pillowy soft cider donut. From Westhampton Beach to nearly the Montauk Lighthouse there are several events worthy of a fall weekend before the conversation turns to talking turkey.
SouthamptonFest, Throughout the town including Agawam Park, Southampton Cultural Center and Southampton Arts Center, Friday, September 29 to Monday, October 2, starting at 6:30 p.m. on September 29.
After two years off, the SouthamptonFest is back with a packed week of arts, shopping, food, and family friendly activities sprinkled throughout the town. Though the official date of the festival is Saturday, things kick off a night early with a cocktail party at 6:30 p.m. at Southampton Arts Center on Friday, September 29, with live performances by Coverland and music from HamptonsDJ. The entrance fee — order tickets early at southamptonrotary.org and save $10 off the normally $40 charge — covers your beer and wine until 8:30 p.m. when a cash bar kicks in for another hour. This weekend you’ll find live concerts, a chowder contest, kids activities like face painting, balloon animals and pumpkin carving, along with art and design showcases, museum exhibits, and a spooky tour of the Rogers Mansion.
Most events are free and don’t require a ticket, except for the kickoff cocktail party and Southampton Cultural Center Gala’s “An Evening of Wine and Roses” on Sunday, October 1, a fundraiser with live entertainment, auctions, food and an open bar. Purchase tickets for the gala here.
Fall Festival for Families, Mulford Farms, 10 James Lane, East Hampton, Saturday, September 30, 10 a.m..
The intact English colonial farmstead at Mulford Farms is the backdrop to the East Hampton Historical Society’s festival, which embraces family fun as it was. Revolutionary War reenactors will provide a glimpse of what life was like on colonial Long Island, which, if nothing else, should help today’s kids appreciate Wi-Fi much more. Costumed interpreters will be on hand to bring history to life along with historic demonstrations of domestic home life. Families can compete in games and craft-making while live music plays in the background, with a grilled hamburger and hot dog lunch for sale from the local Lions Club. The historical society will offer walking tours of the Mulford House, which dates back to 1680. The festival helps celebrate the 375 anniversary of East Hampton with contributions from over a dozen historical organizations from Wainscott to Montauk.
The Greater Westhampton Chamber of Commerce Fall Festival, Main Street, Westhampton Beach, Saturday, October 7, 11 to 4 p.m. (rain date: Sunday, October 8).
Start the day at any of three areas along Main Street, with an arts and crafts show at St. Mark’s Episcopal Church, a farmer’s market at the Village Green, and sidewalks sales at the shops in between. The Gordon Werner arts and crafts show will feature vendors with original and signed works for sale.
Montauk Fall Fest, the green across from Montauk Chamber of Commerce, 742 Montauk Highway, Montauk, starts at 11 a.m. on Saturday, October 7, starts at 10 a.m. on Sunday, October 8.
Arguably the island’s most competitive food event, the Manhattan and New England clam chowder contest is back at the 42nd annual East End Festival (complete with $15 commemorative mugs for sale that can be filled with your preferred stew). But there’s more here than just chowda — live music on Saturday from East End band The Realm, playing a mix of reggae, rock and ska. Hamptons-based Little Head Thinks plays on Sunday with a mix of covers from the 60s through the 90s. Kids can hang out in the bounce slides, two bounce houses, ride the mechanical shark and age-appropriate activities like face painting — and, of course, everyone can enjoy fresh local oysters and clams. Adults can queue up for beer, wine, and hard seltzers from trucks on site and try to win a cash raffle on Sunday.
Wölffer Estate Annual Harvest Party, Wölffer Estate Vineyard, 139 Sagg Road, Sagaponack, Saturday, October 7, at noon (rain date: October 8).
Celebrate Wölffer’s 33rd annual harvest, set in the vineyard of one of the East End’s best wineries. The menu leans toward international flavors of food and drink, with Wölffer’s wines and ciders available. Relive the famous I Love Lucy scene by stomping some grapes, try your hand(s) at barrel rolling or just dance to the live music (maybe even right next to winemaker Roman Roth). Bring the kids for pony and hayrides, plus crafts. Your fee covers all the food and drink, including food trucks, once you enter but plan to bring some cash to score a bottle to enjoy at home.
$190 per adult, $95 for children age 2 to 20; tickets must be purchased in advance.
Oktoberfeast at Amber Waves Farm, Amber Waves Farm, 367 Main Street, Amagansett. Saturday, October 14, 2 p.m..
Join about 250 families for an afternoon of fun and fundraising to support Amber Waves, a nonprofit that aims to train the next generation of farmers and help overcome food insecurity on the East End. There will be games and races for the kids and plenty of food options. Along with produce from Amber Waves, Brooklyn Cured will have charcuterie, Divina Foods will bring olives and antipasti fixings as well as vendors like East End Cowboy, Panadda Sourdough, and Scott’s Protein Balls—think Munchkins, but good for you. If you need a drink after all that cured meat, the locals have you covered with options from Springs Brewery, Wölffer Estate Vineyard, Montauk Brewing Co, and Kidd Squid Brewing. Real East End Brass (REEB) provides live music.
Tickets for adults range from $100 to $150; children 3 to 12 years old are $30 (2 years old and younger are free).
Ghost Hunting at Rogers Mansion, Rogers Mansion, 17 Meeting House Lane, Southampton. Saturday, October 21, 7:30 p.m..
Anyone can get in the mood for Halloween by dressing up, but if you need a bit more adrenalin try running experiments in a 180-year-old mansion, at night, to find ghosts. Join the Southampton History Museum and the Long Island Paranormal Investigators at the Rogers Mansion, where museum staffers along with the plumbers and electricians who maintain the house have reported unexplained phenomena, such as feelings of being watched, seeing shadow people and hearing footsteps and noises in the basement. Participants help with experiments that examine paranormal theories, hear spooky stories, and maybe leave with an encounter all their own.
$40 per adult with tickets available at southamptonhistory.org.
Ragamuffin Parade, Main Street, Sag Harbor, Sunday, October 29, 1 p.m..
While the name certainly suggests you’ll find children strutting their stuff, adults (and pets) can join in the costumed fun too, put on by the Sag Harbor Chamber of Commerce. With the windmill and harbor as the backdrop, marchers will line up on Nassau Street to walk the half-mile or so to the Custom House lawn for games, crafts like pumpkin painting, music, and a bake sale.