Hamptons International Film Festival: East Hampton’s premier film event returns October 2–12, marking its 34th year, with screenings and events across East Hampton, Sag Harbor, and Southampton. Public tickets are on sale now.
Amber Waves’ Oktoberfeast: Saturday, October 3, from 2–5 p.m. This year’s theme celebrates the International Year of the Woman Farmer. Enjoy casual, community-style farm feasting, live music, dancing, and farm tours, with proceeds supporting education, food access, and farmer training (rain date: October 4). Tickets: $75–$100 for adults, $30 for kids.
SouthamptonFest returns for its 14th year on Saturday, October 3 (rain date Sunday, October 4), with festivities kicking off the evening before at the Southampton Rotary Club's kickoff party on Friday, October 2. Southampton Village comes alive with a chowder contest, a petting zoo, a bouncy house, circus acts, sidewalk sales, live music, and family-friendly activities throughout the day.
Wölffer Estate Annual Harvest Party: Saturday, October 10, from 12–4 p.m. at The Wine Stand in Sagaponack — the 35th annual! Enjoy live music, food and beverage stations, barrel-rolling, grape-stomping, hayrides, and more. Tickets are required (rain date: October 11).
Montauk Fall Festival: Saturday, October 10 and Sunday, October 11, 11 a.m.–5 p.m. — the 45th annual! Enjoy local food, live music, and family-friendly activities. Highlights include the Clam Chowder Contest (Saturday only), farmers’ market vendors, kids’ games, and more. Admission is free.
ARF Hamptons’ Stroll to the Sea Dog Walk: Saturday, October 10, gates open at 9 a.m. at Mulford Farm in East Hampton. The Hamptons’ biggest dog event — hundreds of pups and their humans walk to Main Beach and back, with contests, a photo booth, and a silent auction, all benefiting ARF’s shelter and rescue work.
CMEE’s 19th Annual Golf Outing at The Maidstone Club: Thursday, October 15, 11:30 a.m.–7:30 p.m. Golfers enjoy brunch, a 1:30 p.m. shotgun start, and cocktails and hors d’oeuvres on the veranda afterward, benefiting the Children’s Museum of the East End. This event is sold out, but worth inquiring about the waitlist.
Shelter Island Fall 5K Run/Walk: Saturday, October 17, starting at 11 a.m. at Crescent Beach. Now in its 27th year, proceeds support the North Fork Breast Health Coalition, The Coalition for Women’s Cancers, and Lucia’s Angels. There will be post-race BBQ, raffle prizes and more.
If you're only going to catch one art show before it closes, make it LA Monumental at The Ranch in Montauk. It’s three massive outdoor sculptures, including a striking piece built from twelve decommissioned shipping containers, sprawled across the private horse farm's grounds. On view through November 15.
Sag Harbor Ragamuffin Parade: Sunday, October 25, 1:30–2:30 p.m. Participants line up on Nassau Street near the laundromat before the parade steps off, continuing down Main Street to the Whaling Museum lawn, where a carnival hosted by Bridgehampton School's Drama Club wraps things up with games, activities, and music. Dress to impress!
CMEE's Halloween Bash: Friday, October 23, from 4–6 p.m. Designed for families with children ages 2–8, the event features spooky crafts, games, prizes, and dancing. Reservations are strongly encouraged. $5 for members, $25 for non-members.
East Hampton Library Halloween Celebration: Saturday, October 24, from 10 a.m.–3 p.m. Festivities include a costume contest, baking and pumpkin carving/decorating contests, crafts, games, a glow dance party, spooky stories, Halloween movies (including Hocus Pocus), face painting, and historical talks. Prizes awarded. Sign-up required for contests.
Sag Harbor Pumpkin Trail: Saturday, October 31, from 1:30–3:30 p.m. Children in costume can trick-or-treat at Chamber-member stores displaying a Pumpkin Trail sign.
No better 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
For all the farm visits, this barn jacket couldn’t be more perfect with my favorite bandana scarf.
Stay tuned for a bigger Halloween round-up, but if you’re hitting up those pumpkin patches early, give them a little decoration!
We always have a million bags when we’re driving back-and-forth for the weekend, and this could be a nice little upgrade (love the bow!) for the car, would make for a great diaper bag, too.
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!
Do you know that Round Swamp does Thanksgiving? A perfect option for those who aren’t interested in cooking but still want something delicious (linked menu option from 2025)
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. And, I also have big dreams for outdoor pizza parties with this pizza oven.
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