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
Speed dating at Mim's in Roslyn Heights for singles 34 to 48, structured rounds so you actually talk to people instead of swiping. The restaurant's on Roslyn Road with its own lot, and the event runs about two hours with breaks between rotations. Easier than another month of apps.
- 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 +
This singles meetup for the 40-plus crowd takes on the aerial obstacle courses and ziplines at Adventure Park, with harnesses and guides handling the safety logistics. The tree-based course runs about two hours depending on your group's pace, and the Wheatley Heights location keeps things central for most of the Island. Earlier time slot means you'll finish before dark.
- 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
Singles in their 20s through 40s tackle ziplines and aerial obstacle courses as the sun sets at Adventure Park in Wheatley Heights. The tree-lit course adds some atmosphere while you're clipped in 30 feet up, and the group setup makes it easier to chat between challenges. Colonial Springs Road location has its own lot off the Southern State.
- 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 multiple spots along Farmingdale's Main Street, starting at Tap House at 7pm. Expect rotating stops for drinks, food, and dessert as you meet other unattached locals. Farmingdale's got solid parking in the municipal lot behind Main, so you won't waste time circling.
- 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 up a vintage truck planter at this hands-on workshop at Nest on Main in Northport. Toni and Holly walk you through turning it into a fall centerpiece you actually take home. Main Street parking can be tight on a Wednesday evening, so give yourself extra time.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
Appreciating the Virtues of the Autumn Garden: Lecture and Walk
Vincent Simeone walks Landcraft's gardens pointing out which plants actually shine in fall—asters, ornamental grasses, late-blooming shrubs that most people overlook. It's part lecture, part stroll through 10 acres in peak autumn mode. Bring your own notebook if you want to remember plant names.
- 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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