What’s Happening in the #Hamptons During Fall Shoulder Season


Mon-Tiki sails into October.

Now that the cold, cold winds of fall have blown through the Hamptons (and summer residents and their controversial Ubers and Blades and post-apocalyptic parties have almost faded from memory), it’s time to enjoy the shoulder season. That’s right — despite ominous terms like “Tumbleweed Tuesday,” which we ourselves use with abandon — there’s still lots to do in the Hamptons in the fall. Skies are cornflower blue, the ocean is gloriously warm, and there’s nary a Range Rover or G-Wagen on the road.  Who says summer is the best season on the East End?

Below is a smattering of offerings to enjoy. As usual, listings on the Hampton Bee calendar must meet the following criteria: Events must support local businesses; we’d actually have to be interested in attending them; and they must involve booze. (We jest. Drink responsibly, kids.) If you’ve got something to add to our list, please email us at thehamptonbee@gmail.com.

Shelter Island

  • Ram's Head InnThe Ram’s Head Inn has live music featuring Jon Divello Band on Friday nights (Oct. 9 and Oct. 23), while its popular Sunday Night Jazz series continues through Columbus Day.  The inn also plans its first ever Oktoberfest on Oct. 17, which will include live music, a pig roast and onsite tastings from East End vineyards and breweries ($35 per person). The inn plans its annual Halloween celebration on Oct. 31, 10 p.m. to 1 a.m., no cover charge. For more information visit the inn’s website or call 631-749-0811. 108 Ram Island Drive, Shelter Island Heights. 


  • Wolffer Estate Vineyard will host its annual celebration of the grape harvest on Oct. 10 (Rain date: Oct. 11) featuring live music by Clinton Curtis, food and beverages made by Wolffer, grape-stomping, barrel-rolling, pony rides, face-painting and more. General admission tickets are $135 per person, with discounts for children and wine club members. More info here3312 Montauk Highway, Sagaponack.
  • Townline BBQ restaurant, which is open Thursdays through Mondays, has an array of happy hour and football specials, including $3 Lone Star Longneck bottles and $2.50 hush puppies with chipotle mayo. (We didn’t know what a hush puppy was either; here’s a link. Looks…healthy?) 3593 Montauk Highway, Sagaponack.

Sag Harbor

  • south-fork-ferry

    GeekHampton hosts the “Meet the Artist” series.

    GeekHampton, the tech shop that specializes in Apple products, continues its exhibition series featuring local artists who use technology in their work. The latest show showcases the work of John and Amy Wickersham and is on view through Oct. 31, with an opening reception (complete with free wine from Long Wharf Wines) on Oct. 9 from 6 p.m. to 8 p.m. 34 Bay Street, Sag Harbor.


  • Almond restaurant kicks off Artists & Writers Night, an off-season series featuring creative-type speakers, on Oct. 13 at 7 p.m. with artist Tucker Marder. The evening will feature a family-style three-course menu by executive chef Jason Weiner. The cost is $45, which includes a local beverage, tax and gratuity. Reservations required; call 631-537-5665. 1 Ocean Road, Bridgehampton.

East Hampton

  • Guild Hall has an ongoing exhibit, Roy Lichtenstein: Between Sea and Sky, on view through Oct. 12. Museum hours: Monday-Friday-Saturday, 11 a.m. to 5 p.m.; Sunday, 12 p.m. to 5 p.m158 Main St., East Hampton.
  • YMCA East Hampton RECenter will host a Fall Festival for families on Oct. 10, 9 a.m. to 2 p.m., featuring a pumpkin hunt, an inflatable slide, face painting and a petting zoo. Pre-registration required at 631-329-6884 or sondra.vecchio@ymcali.org. 2 Gingerbread Lane, East Hampton.


  • Indian Wells Tavern is offering fall football specials on Sunday and Monday, for those who like tasty nibbles and pours with their pigskin. A special snacks menu (did someone say moules frites?) is offered on Sunday nights, while a special drinks menu (hello, pumpkin ale) is featured on Mondays. 177 Main Street, Amagansett.


  • Mon-Tiki, Montauk’s charter catamaran helmed by Capt. David Ryan, will be running a full schedule of public, private and corporate trips through September and into October. The vessel was built on the East End; read a related Hampton Bee story here. Visit the Mon Tiki site or call 631-668-2826. 59 Star Island Rd, Montauk.
  • Montauk Chamber of Commerce hosts the 34th Annual Fall Festival, a family-oriented event on the Green, Oct. 10 and 11. The event features a (renowned) clam chowder contest, live music from Gene Casey and the Lone Sharks, Long Island beers and wine, Octoberfest foods and offerings from the Montauk Farmers Market. More details here.


  • Ashawagh Hall hosts the 10th anniversary of the Plein Air Peconic exhibition, featuring painters and photographers whose work showcases land preserved by the Peconic Land Trust. Opening reception is Oct. 10, 5 p.m to 8 p.m.; the exhibit is on display the entire Columbus Day weekend. 780 Springs Fireplace Road, East Hampton.


  • Southampton Farmers’ Market continues through Oct. 11, with local vendors offering vegetables, fruits, pickles and more, 9 a.m. to 2 p.m. 25 Jobs Lane, Southampton.

Got something to add? Please email thehamptonbee@gmail.com


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