Fall on the East End: Your Guide to Long Island's Best Autumn Events
Updated: Sep 17
Happen to be house hunting this season? Every festival, fair, and fall celebration below is a great excuse to explore a neighborhood, grab a coffee, and then swing by a nearby open house to see what's for sale. Think of it as a weekend built around discovery — of new traditions, new favorite spots, and maybe, just maybe, your new home.
Here's what's happening around Long Island this fall.
Weekend of September 20
The Cooperage Inn 27th Annual Fall Festival Kick off the season with live music from Slingshot, family fun, and the kind of outdoor gathering that makes fall feel official. 📍 Cooperage Inn, Baiting Hollow | 🕐 1:00 PM
5th Annual Family Country Festival Pumpkin patch, hay rides, a petting zoo, and a beer garden for the grown-ups — this one has something for every member of the family. 📍 Bay Gardens, East Moriches | 🕐 11:00 AM
Longwood Fair A full day of craft vendors, food trucks, a beer garden, historical reenactments, and hands-on crafts for the kids. 📍 Longwood Estate, Longwood and Smith Roads, Ridge | 🕐 10:00 AM–6:00 PM | 💵 $5 | islandfairs.com
Weekend of September 26–27
Fall Antiques, Fine Art and Craft Fair Browse fine art, photography, antiques, silver, jewelry, pottery, and handmade treasures while live music plays in the background. 📍 Southold Historical Society, 55200 Rte. 25, Southold | 🕐 9:00 AM–4:00 PM | 💵 $5 | oldtownartsguild.org
Hallockville Country Fair and Craft Show Step back in time with tours of historic homes and outbuildings dating from 1765 to 1937, plus artisan vendors, food trucks, live music, children's games, and traditional craft demonstrations. 📍 Hallockville Museum Farm, 6038 Sound Ave., Riverhead | 🕐 10:00 AM–4:00 PM | 💵 $12 | hallockville.org
Wading River – Shoreham Chamber of Commerce Fall Festival A community favorite with local vendors and family-friendly fun. 📍 The Shoppes at East Wind, Wading River | 🕐 11:00 AM
October 2–12
Hamptons International Film Festival One of the region's marquee events, bringing acclaimed films, filmmakers, and film lovers to the East End for ten days of screenings and celebration. 📍 Locations throughout the Hamptons
Weekend of October 3–4
Fall Fine Art, Crafts & Antiques Fair A charming stroll through historic Cutchogue, filled with fine art, photography, jewelry, pottery, and handmade wood items. 📍 Cutchogue Village Green Historic Buildings, Main Road, Cutchogue | 🕐 9:00 AM–4:00 PM (rain date Oct. 4) | 💵 $3 | oldtownartsguild.org
SouthamptonFest Live entertainment, food, art, and a farmers market fill Southampton Village. Kick things off the night before at the Rotary Kick Off Party. 📍 Southampton Village | 🕐 Noon–6:00 PM (rain date noon–4:00 PM Oct. 4) | 💵 Free (Kick Off Party is ticketed) | scc-arts.org
Weekend of October 10
Fall Festival Over 60 vendors, food trucks, live music, a bounce kingdom, a petting zoo, aerialists, and a farmers market line Main Street for a day the whole family will remember. 📍 Main Street (Library Ave. to Moniebogue Lane), Westhampton Beach | 🕐 10:00 AM–5:00 PM (rain date Oct. 12) | 💵 Free | westhamptonchamber.org
Weekend of October 17-18
Port Jefferson Harvest Festival Two full days of seasonal, family-friendly fun with activity passes available throughout the village. 📍 Port Jefferson Village | 🕐 12:00 PM–5:00 PM
Weekend of October 24
Bats, Barnacles & Broomsticks Halloween Party Trick-or-treating, vendor tables, games, and prizes make this a spook-tacular way to celebrate Halloween a little early — plus, it's included with aquarium admission. 📍 Long Island Aquarium, 431 E. Main St., Riverhead | 🕐 10:00 AM–4:00 PM | 💵 Aquarium admission: $52.50 adults, $37.50 ages 3–12, $38.50 ages 62+ (half price for costumed kids 3–12 with a paying adult)
Make It Part of Your House-Hunting Weekend
If you're currently searching for a home on Long Island, why not turn your open house tour into a full day out? Visit a listing in the morning, then head to a nearby fair or festival in the afternoon. It's a great way to get a real feel for a neighborhood — its restaurants, its community events, its energy — not just the house itself. After all, you're not just buying a home, you're buying a lifestyle, and fall on the East End is a pretty wonderful preview.
However you spend your weekends this fall, we hope you get outside, try something new, and make a few memories along the way. And if any of these outings happen to end with you falling for a neighborhood — or a house — give me a call. I'd love to help you find your way home. Reach out to Ted anytime to start the conversation about buying or selling on Long Island.
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