Festivals
Long Island's festival circuit — village street fairs, harbor festivals, harvest fests, beer + wine festivals, food truck rallies.
Editor's Pick Northport Fall Festival
Northport Village's signature street festival shuts Main Street down for a full Saturday of food trucks, live music on the harborfront stage, kids' rides, and 100+ local vendors. Park on Bay Avenue by 10:30 AM — the main lot fills by 11. The food vendor lineup at the village green is the highlight; line up by noon for the first wave before the lunch rush.
- When
- Where
- Northport Village, Northport
Editor's Pick Oyster Bay Oyster Festival — 200K Visitors, One Weekend
Long Island's biggest single annual event — 200,000+ visitors descend on Theodore Roosevelt Park in Oyster Bay over a mid-October weekend for $1 oysters, 100+ food vendors, 250+ craft stalls, multi-stage live music, a tall ship in the harbor, and the working-fishing-village atmosphere that the Hamptons don't have. Free admission. Forty-plus years of history. The LI fall event of the year.
- When
- Where
- Theodore Roosevelt Memorial Park, Oyster Bay
Greenport Maritime Festival — North Fork Harbor Weekend
Greenport's annual Maritime Festival turns the working harbor village into a regional weekend destination — tall ships in the harbor, oyster shucking competitions, traditional whaleboat races, food + craft vendors along Front Street, live music throughout. Free admission. The locals' East End fall favorite.
- When
- Where
- Greenport Village Harbor, Greenport
Editor's Pick 7 in Heaven Singles Speed Dating Age B 34-48 Roslyn
7 in Heaven hosts speed dating at Mim's in Roslyn Heights for the 34-48 crowd—actual face-to-face rounds instead of swiping. Starts at 7:30 PM on a Friday night. Roslyn Road has street parking but it fills up fast, so the municipal lot behind the strip is your better bet.
- When
- Where
- Mim's Restaurant, Roslyn Heights
- Price
- See ticket page
Editor's Pick 7 in Heaven Singles Zip-lining and Obstacle Course Ages 40's 50's 60's +
Same Adventure Park zipline course as the younger singles group, but this one's geared for 40s-60s+ and starts an hour earlier at 1:30 PM. 7 in Heaven runs it as a mixer while you're clipped into harnesses navigating tree platforms. Parking's easy in the dedicated Adventure Park lot off Colonial Springs.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
Editor's Pick Singles ages 20's 30's 40's Fall Twilight Ziplining @ Adventure Park
7 in Heaven organizes a singles meetup at the Adventure Park's aerial course, timed for sunset so the tree obstacles are lit as dusk falls. This session targets 20s-40s and starts at 2:45 PM. Colonial Springs Road is tucked behind the Westfield South Shore Mall if you're GPS hunting.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
Harbes Family Farm — Pumpkin Picking + Winery Weekend
Harbes Family Farm in Mattituck combines a working farm + pumpkin patch + corn maze + on-site winery — making it the locals' pick for an East End fall day-trip with both kid-friendly farm activities and adult winery tastings. Open daily mid-September through Halloween.
- When
- Where
- Harbes Family Farm, Mattituck
- Price
- See ticket page
7 in Heaven Singles Fun Food/Drink Pub Crawl + Speak Easy Farmingdale
This singles pub crawl hits three spots on Farmingdale's Main Street—appetizers at one, drinks at another, dessert at the last. Starts at Tap House at 7pm and everything's walkable from there. Good setup if you're tired of dating apps and want to meet people while trying new places.
- When
- Where
- Tap House Farmingdale, Farmingdale
- Price
- See ticket page
7 in Heaven Singles Fun Food/Drink Pub Crawl + Speak Easy Farmingdale
This singles pub crawl kicks off at Tap House on Main Street and hits multiple Farmingdale spots for food, drinks, and dessert. Parking can be tight on Friday nights, so arrive early or use the municipal lot on Front Street. Ages and group size vary, but expect a casual bar-hopping vibe with built-in conversation starters at each stop.
- When
- Where
- Tap House Farmingdale, Farmingdale
- Price
- See ticket page
Long Island Fall Festival — Pumpkin Picking + Cider Weekend
Long Island's farm trail comes alive in October with pumpkin picking, hayrides, cider donuts, and corn mazes across two dozen working farms in Nassau and Suffolk. The Wednesday + Thursday before peak weekends are dramatically less crowded. Bring cash for many farm stands; not all take cards.
- When
- Where
- Long Island Farm Trail (multiple locations), Long Island
- Price
- See ticket page
Create a Beautiful Fall Centerpiece Planter with Toni & Holly!
You'll collage and plant a vintage truck planter at this workshop on Northport's Main Street. Toni and Holly walk you through making a fall-themed centerpiece you take home that night. Street parking along Main or the lot behind the storefronts.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
Appreciating the Virtues of the Autumn Garden: Lecture and Walk
Vincent Simeone leads a lecture and walk through Landcraft's gardens, focusing on plants that actually shine in fall—late-blooming perennials, ornamental grasses, and trees with good color. October 24 is prime time for North Fork foliage, so you'll see these varieties at their peak. Starts at 10 AM with parking at the foundation.
- When
- Where
- The Landcraft Garden Foundation, Mattituck
- Price
- See ticket page
7 in Heaven Speed Dating Lunch Singles Ages 44-59 Hauppauge
Speed dating over lunch at Simplay brings together singles in their 40s and 50s (women 44-57, men 47-59) for quick, face-to-face conversations. The venue's off Commerce Drive in Hauppauge's office park area, so parking's easy. Seven-minute rounds mean you'll meet a dozen people without committing your whole Sunday.
- When
- Where
- Simplay, Hauppauge
- Price
- See ticket page
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