The October Hamptons Issue
Here's the monthly guide to what's happening in October Out East. There's some fantastic fall festivals and lively Halloween events, plus my favorite recipe for pumpkin muffins..
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SouthamptonFest 2025: Friday, October 3 through Sunday, October 5. This weekend-long celebration highlights local life, community, and culture with food vendors, live entertainment, family activities, and arts events throughout the village.
Wölffer Estate Annual Harvest Party: Saturday, October 11, from 12–4 p.m. at The Wine Stand in Sagaponack. Enjoy live music, food and beverage stations, barrel-rolling, grape-stomping, hayrides, and more. Tickets are required (rain date: October 12).
44th Annual Montauk Fall Festival: Saturday, October 11 and Sunday, October 12, from 11 a.m. to 5 p.m. Enjoy local food, live music, and family-friendly activities. Highlights include the Clam Chowder Contest, farmers’ market vendors, kids’ games, and more. Admission is free.
Amber Waves’ Oktoberfeast Fundraiser: Saturday, October 18, from 2–5 p.m. This autumn event features farm-to-table food, live music, dancing, and farm tours, benefiting education, food access, and farmer training.
CMEE’s Halloween Bash: Friday, October 24, from 4–6 p.m. Designed for families with children ages 2–8, the event features spooky crafts, games, prizes, and a costume contest. Reservations are strongly encouraged.
East Hampton Library Halloween Celebration: Saturday, October 25, from 10 a.m.–3 p.m. Festivities include a costume contest; baking and pumpkin carving/decorating contests; crafts; games; a glow walk; spooky stories; movies; face painting; and historical talks. Prizes awarded. Sign-up required for contests.
Haunted Village at the Southampton History Museum: Saturday, October 25, from 11 a.m.–4 p.m. Experience a fun, historical Halloween event featuring trick-or-treating, a costume contest, 19th-century music, and chilling Long Island folklore.
Sag Harbor Pumpkin Trail: Friday, October 31, from 3–5 p.m. on Sag Harbor’s Main Street. Children in costume can trick-or-treat at Chamber-member stores displaying a Pumpkin Trail sign.
Sag Harbor Ragamuffin Parade: Sunday, October 26, at 1 p.m. Participants should line up on Nassau Street near the laundromat before the parade steps off. The procession will continue down Main Street to the Custom House lawn, featuring games, activities, and dance music for all ages.
Autumn Golf Outing Benefit at The Maidstone Club supporting the East Hampton Historical Society: Wednesday, October 15, starting at 11:30 a.m. Includes lunch, practice on the range and green, followed by a reception and awards. Foursomes and individual tickets available.
Shelter Island Fall 5K Run/Walk: Saturday, October 18, starting at 11 a.m. (rain or shine) at Crescent Beach. Proceeds support breast and women’s cancer charities. Post-race BBQ, raffles, awards, and team options included.
Hamptons International Film Festival: East Hampton’s premier film event returns Friday, October 3 to Monday, October 13, showcasing narrative and documentary features and shorts from around the world.
It’s a great time to visit the farms! We love Fairview Farm at Mecox for the corn maze and pumpkin picking, Seven Orchards for apple picking, and of course, Hank’s Pumpkintown for all the entertainment, check out my Hamptons Farm guide for a comprehensive guide of all the farms
If you’re planning on spending Thanksgiving Out East, I highly recommend ordering your turkey from Mecox Bay Dairy (available for preorder now). Everyone in our family agrees: it’s the best turkey we’ve ever had!
I have kids who get carsick, and we try to avoid too much screen time. I cannot recommend the Yoto Mini player enough. Truly, it’s game changing for car rides, bedtime and quiet time. It offers the best stories and book series like The Gruffalo, The Chronicles of Narnia, Beatrix Potter, BrainBots, and so so much more. But don’t forget the headphones!
With the chilly weather ahead, I’m eyeing one of these portable fire pits for our backyard. I have grand visions of big s’mores parties with these perfect sticks and boxes.
I love a seasonal bake, so every October and November, we religiously bake these pumpkin muffins. They’re super easy, and my kids think they’re delicious.
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