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
Editor's Pick Sayville Summer Family Fair
Sayville Village's annual summer family fair on Main Street. Carnival rides for kids 3-12, food trucks, live family music, free face-painting + crafts, fire-truck climb-on, beer garden in a separate adults-only zone. Free admission, ride wristbands $20. The South Shore family Saturday at its peak.
- When
- Where
- Downtown Sayville Main Street, Sayville
Editor's Pick 7 in Heaven Singles Speed Dating Age C+ 50-65 Roslyn
Speed dating for singles 50-65 at Mim's in Roslyn Heights, starting at 4pm. It's the in-person alternative to endless swiping—structured rounds that actually get you talking to real people in the same room.
- When
- Where
- Mim's Restaurant, Roslyn Heights
- Price
- See ticket page
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 Speed Dating for Long Island Singles Ages 40-55 Hauppauge
Speed dating in Hauppauge for singles 40-55 (women 40-53, men 42-55) at Simplay on Commerce Drive. Structured face-to-face meetings—no profiles, no messaging back and forth for weeks before meeting.
- When
- Where
- Simplay, Hauppauge
- 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 X-Treme Bowling & Mixer Ages 50's 60's + Levittown
Casual bowling mixer for singles 50s-60s and up at Levittown Lanes on Tanners Lane, 7pm start. Low-pressure, non-competitive games—more about meeting people than your score.
- When
- Where
- Levittown lanes, Levittown
- Price
- See ticket page
7 in Heaven Singles Forks & Flirts: Cozy Dinner Party 40s 50s 60s+ Mineola
Italian dinner party for singles in their 40s, 50s, and 60s at Eric's Italian Bistro in Mineola. Tables are organized by age groups, so you're eating and talking with people in your range. It's on East Old Country Road, easy to find with parking out front.
- When
- Where
- Eric's Italian Bistro, Mineola
- Price
- See ticket page
7 in Heaven Singles Speed Dating Age B 34-48 Lindenhurst Village
Speed dating for singles 34-48 at The Green Door in Lindenhurst, where you'll cycle through short conversations instead of swiping through profiles. The bar's on North Wellwood Avenue in the village, with street parking nearby. Beats another night scrolling through apps.
- When
- Where
- The Green Door, Lindenhurst
- Price
- See ticket page
7 in Heaven Singles Events Speed Dating Age C 44-59 Hicksville
Speed dating for the 44-59 crowd at Vitality Lounge in Hicksville. You'll meet other singles face-to-face in timed rounds—actual conversations, no profiles. The lounge is on South Broadway near Broadway Mall.
- When
- Where
- Vitality Lounge, Hicksville
- 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
NEW! Lemon Topiary Making Class - Hosted by All Set By Gabrielle
All Set By Gabrielle shows you how to build a faux lemon topiary in a chinoiserie ginger jar from the ground up. You'll arrange, wire, and style the whole thing yourself, then bring it home as table decor. Nest on Main is on Northport's Main Street with easy street parking nearby.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
Create a Beautiful Fall Centerpiece Planter with Toni & Holly!
Collage a vintage pickup truck planter into a seasonal centerpiece using fall florals and whatever else Toni and Holly have lined up. This is at Nest on Main in Northport, walkable from the harbor if you're grabbing dinner before or after.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
7 in Heaven Singles Zip-lining and Obstacle Course Ages 40's 50's 60's +
This zipline and aerial obstacle session is tailored for singles in their 40s, 50s, and 60s, starting at 3:45 PM before the younger crowd arrives. You'll tackle tree-to-tree platforms and ziplines with people in a similar age range, all looking to meet someone while clipped into a safety harness. Adventure Park is off Colonial Springs Road in Wheatley Heights.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
Singles ages 20's 30's 40's Twilight Ziplining @ Adventure Park
A singles mixer for the 20s-through-40s crowd happens on the tree-lit zipline and obstacle courses at Adventure Park after 4:45 PM. You'll clip in alongside other unattached people navigating aerial platforms as the sun sets. It's part social event, part adrenaline—expect to actually talk to strangers while suspended in harnesses.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
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