Fall Festival at Good Ground Park
When: Friday, October 17th, 2025
4pm – 6pm
Where: Good Ground Park, 9 Squiretown Rd, Hampton Bays, NY
Bring your pre-carved pumpkin and enter to win the coveted prize for funniest or scariest pumpkin! There will be lawn games, a food truck, pumpkin decorating, a costume parade, and more!
BookHampton: An Evening with Caroline Sutton
When: Saturday, October 18th, 2025
6pm
Where: BookHampton, 41 Main St, East Hampton, NY
Natural history writer Caroline Sutton will discuss her latest collection of essays, Eyes in the Soles of My Feet, with naturalist Carl Safina. The essays explore the secrets of the natural world, perfect for nature lovers.
Shelter Island’s 26th Annual Fall 5K Run/Walk
When: Saturday, October 18th, 2025
11am – 2pm
Where: Crescent Beach, 35 Shore Road, Shelter Island, NY
Walk or run with your family and friends, all in honor of Breast Cancer Awareness month! The 5K course will kick off at Crescent Beach!
32nd Annual Landmarks Luncheon
When: Saturday, October 18th, 2025
11:30am – 2:30pm
Where: Maidstone Club, 50 Old Beach Ln, East Hampton, NY
The Landmarks Committee of the Ladies’ Village Improvement Society (LVIS) will host its annual Landmarks Luncheon at the Maidstone Club, bringing attention to a deeply significant chapter in East Hampton’s history: the story of Freetown.
Amber Waves’ Oktoberfeast
When: Saturday, October 18th, 2025
2pm – 5pm
Where: Amber Waves, 367 Main St, Amagansett, NY
Enjoy an autumn afternoon with seasonal dishes made with locally grown ingredients, live music and dancing, and fun family games for adults and kids!
Cab Franc Forward Winemaker’s Dinner
When: Sunday, October 19th, 2025
5pm
Where: The Pridwin, 81 Shore Rd, Shelter Island, NY
Enjoy a spectacular evening with a multi-course menu concocted by Executive Chef Todd Ruiz, pairing perfectly with Cabernet Sauvignon, New York State’s premier red wine.
Bridgehampton Chamber Music BCM Autumn: Brooklyn Rider
When: Saturday, October 18th, 2025
5pm – 6:30pm
Where: Bridgehampton Presbyterian Church, 2429 Montauk Highway, Main St, Bridgehampton, NY
The string quartet will return to Bridgehampton with an incredible program featuring pieces by Haydn, Matana Roberts, Beethoven, and more.
Wolffer’s Candlelight Fridays
When: Friday, October 17th, 2025
4pm – 7pm
Where: The Tasting Room, 139 Sagg Road, Sagaponack, NY
A perfect date night at Wolffer with live music, seasonal pairings, and light bites.
Like No One Exhibition in East Hampton
When: Fri, October 17th – Sun, Oct 19th, 2025
Where: Ashawagh Hall, 780 Springs Fireplace Road, East Hampton, NY
Renowned fine artist Michael McDowell, known for his figurative and plein air works, will exhibit at Ashawagh Hall. The opening reception will be on Saturday, October 18th, from 4 pm to 8pm.
