When does Montauk's year end? Columbus Day weekend is the usual answer. The 45th Fall Fest filled the Town Green on Oct. 10 and 11 with farmers-market vendors, live entertainment and the Saturday chowder contest. The Montauk Historical Society sets a later date. It lights Montauk Point Lighthouse on Saturday, Nov. 28, and the museum and grounds close for the season after that day.
That date sets the end of the late season. Everything between now and then builds toward it, through a calendar that gets thinner before it gets busy again. This year Main Street is also missing the counter where much of the off-season used to happen.
Main Street Lost Its Counter in September
Herb's Market closed for good at the end of September. Harold "Herb" Herbert opened it at 778 Montauk Highway in 1963 as a grocery, deli and butcher shop. The East Hampton Star reported that it grew into an unofficial social center for the hamlet, a place where locals and visitors could catch up with each other. The owners, Joe Ferraro and his parents, Carl and Diane Ferraro, announced the closing on social media. The post drew thousands of views and hundreds of comments, and many of them were about the fried chicken, the sandwiches, the coleslaw and the "You can't beat Herb's meat" T-shirts.
Jack Perna, the retired Montauk School superintendent, described the shop to The Star in plain terms. "It was like a mini post office," he said. "People were always there." He also remembered "always a few firemen standing outside chatting with Herb."
That is why the closing matters most in the months ahead. In July, a deli counter is one of many places to run into people. In November, with the summer crowd gone, those places count for much more. The Ferraros planned to sell the equipment and fixtures, and as of mid-October no new business had been announced for the space.
The groceries are still easy to find. Montauk IGA describes itself as open all year, with meat, dairy, groceries, produce and a deli. Tony's Meat Market has butchery, deli sandwiches, groceries and prepared grab-and-go meals. Visit Montauk's guide last winter listed Tony's as open every day, alongside Hampton Coffee Co., M&R Deli and Pizza Village. The meeting place is harder to replace than the groceries, and so the hamlet's few scheduled events carry more weight between now and the end of November.
The Calendar Thins Before It Gets Busy Again
From Halloween to mid-November, Montauk has about one event a weekend. Each one is hosted by a single place, and each is the kind of night that only works once the summer crowd has gone home.
- Saturday, Oct. 31: The Halloween Party at Backyard Restaurant at Solé East Resort, listed on the Montauk Chamber of Commerce calendar.
- Friday, Nov. 6, through Sunday, Nov. 8: Murder Mystery Weekend at The Montauk Manor.
- Saturday, Nov. 14: Girls' Night Out at Gurney's Montauk, a benefit for Lucia's Angels and the Coalition for Women's Cancers.
Gurney's has also set its fall schedule around weeknights. Gigi's started a fall and winter prix fixe on Oct. 12, served Sunday through Thursday and not on holidays. Sunset Hour at Gigi's Bar runs 4 to 6 p.m., Sunday through Thursday, from Oct. 12, 2026, to April 15, 2027. That schedule runs six months and stops for no holiday weekend. It is a full winter of standing weeknight plans, and it is posted in advance.
The lighthouse is open through these weeks on a shorter fall schedule. It opens Friday through Monday in October, then Friday through Sunday in November with a 3:30 p.m. closing time, and on Nov. 28 it closes at 2:30 p.m., ahead of the evening lighting. General admission is $15.
Four Days at the End of the Hamlet
Thanksgiving week is when Montauk's late calendar comes together. Four days hold most of what is left of the year's public occasions:
- Thursday, Nov. 26, 10 a.m.: The John Keeshan Memorial Montauk Turkey Trot starts on the west side of the Circle, and the event page lists the location as 742 Montauk Highway. Gurney's serves Thanksgiving dinner that evening as part of a holiday weekend running Nov. 25 through 29.
- Friday, Nov. 27: The lighthouse grounds are open for one of their last days. Check the Historical Society's seasonal hours page for times before you drive out to the Point.
- Saturday, Nov. 28, from 4 p.m.: Lighting the Lighthouse at 2000 Montauk Highway. It begins around dusk with singalong holiday music from Sarah Conway and the Playful Souls and hot chocolate donated by Hampton Coffee. The light goes on at about 5:15 p.m. The event is free, and the Society welcomes donations. The seasonal hours page has the evening running until 7:30 p.m.
- Sunday, Nov. 29, 11 a.m. to 2 p.m.: Santa at the Light, with photos with Santa, Hampton Coffee hot chocolate and cookies from Montauk Bake Shoppe. It is also free, with donations accepted.
The order matters. Saturday is the last day for the museum and grounds, so the lighting is the season's final public evening at the Point as well as a holiday event. After Nov. 28, the Society keeps only the gift shop open, on weekends through Dec. 20, with limited hours that depend on the weather. For anyone with holiday shopping in mind, those December weekends are the last chance to buy from the lighthouse until it reopens in spring.
The local names on the Society's two event pages are worth noticing. Hampton Coffee, which Visit Montauk listed last winter as open every day, supplies the hot chocolate both days. Montauk Bake Shoppe supplies the Sunday cookies. The season closes with the businesses that stay open year-round.
December Moves Back to the Town Green
After Thanksgiving, the calendar moves from the Point back to the center of the hamlet. The fifth annual Magic of Montauk Holiday Fair is Saturday, Dec. 12, presented by the Montauk Chamber of Commerce and Visit Montauk. Plans include a lit holiday path around the Town Green, vendors, a hot cocoa contest, activities for children, food trucks, beer and wine, live music, photo spots, Santa and live reindeer. The listing gives no start or end time yet, so the Chamber's page is the one to check closer to the date.
For eating out once December arrives, the best guide is last winter's list, used with care. In January 2026, Visit Montauk named these restaurants as open for winter: Montes @ The Manor, Shagwong Tavern, The Bird, Inlet Seafood Restaurant, The Point Bar and Grill, Muse at the End, Tauk at Trails End, 668 The Gig Shack, John's Drive-In, John's Pancake House, Naturally Good Foods & Cafe, Harvest on Fort Pond, Gigi's at Gurney's, and Marlena's Packout for drinks only. The same guide warned that hours may vary. This winter's schedules have not been posted yet, so call before you go.
One more name may join the list. Este is under construction on Montauk Highway next to Offshore Montauk. Marley Dominguez, managing partner of Enduring Hospitality, the company behind it, told the town's Planning Board he plans to keep the restaurant open year-round. He said he would move the rooftop seating down to the ground floor for the winter, and he described "a place where people can come together for sunsets in the summer and gather around the fireplaces in the winter," 27east reported. At the time of that report, completion was expected later this year. For now it is an announced plan, and the building is still under construction.
Until then, the year-round places to gather are the ones already listed here: a deli or butcher counter, Gigi's on a weeknight, and the lawn beneath the lighthouse at 5:15 p.m. on Nov. 28.
If you are spending more of the off-season in Montauk this year and want help with your property between now and spring, from house checks to setting up winter services, The Lori Schiaffino Team can help you set it up quietly and well. Work With Us.
