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 Learn How to Save Seeds!
Learn which vegetable and flower seeds are worth saving from this year's garden to plant next season. This free workshop at the Patchogue library covers practical techniques for harvesting, drying, and storing seeds that'll actually germinate. Saves you money and keeps your favorite varieties going year after year.
- When
- Where
- Patchogue-Medford Library, Patchogue
Editor's Pick Singles Dine & Dance Sit-Down Dinner Party Patchogue
This sit-down dinner at Ristegio's on Medford Avenue seats singles by age group before a live band kicks off around 7pm. Doors open at 5:30pm on Saturday night. Patchogue's walkable downtown means you can easily bar-hop before or after if the vibe's right.
- When
- Where
- Ristegio's Restaurant & Lounge, Patchogue
- Price
- See ticket page
Editor's Pick 7 in Heaven Singles Events Speed Dating Age C+ 50-65 Hicksville
Speed dating for the 50-65 crowd happens at Vitality Lounge on South Broadway in Hicksville this Sunday at 4pm. Structured rounds mean you'll actually talk to people instead of swiping through profiles all weekend.
- When
- Where
- Vitality Lounge, Hicksville
- 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 Speed Dating Age A+ 30-44 Bay Shore Downtown
Speed dating at Fire Island Vines in downtown Bay Shore for singles 30-44. You'll rotate through quick conversations over drinks—way faster than endless messaging. Main Street has metered parking, or use the municipal lot behind the strip.
- When
- Where
- FIV Fire Island Vines, Bay Shore
- Price
- See ticket page
7 in Heaven Singles Fun Food/Drink Pub Crawl + Speak Easy Farmingdale
A pub crawl through downtown Farmingdale hitting multiple spots for food, drinks, and dessert with other singles. Starts at Tap House on Main Street and moves from there—Farmingdale's walkable bar scene makes this easy. Street parking or use the LIRR lot if you're training in.
- When
- Where
- Tap House Farmingdale, Farmingdale
- Price
- See ticket page
7 in Heaven Speed Dating Lunch Singles Ages 44-59 Hauppauge
Speed dating over lunch in Hauppauge for singles roughly 44-59. Meet people face-to-face at Simplay instead of scrolling through profiles all weekend. The venue is in a commercial plaza off Vets Highway with easy parking.
- When
- Where
- Simplay, Hauppauge
- Price
- See ticket page
7 in Heaven Singles Speed Dating Age B 34-48 Roslyn
Speed dating at Mim's in Roslyn Heights for singles 34-48. Quick, structured conversations with real people instead of another night on the apps. Parking lot on-site, and you're near the Roslyn village strip if you want to walk around before or after.
- When
- Where
- Mim's Restaurant, Roslyn Heights
- Price
- See ticket page
7 in Heaven Singles Zip-lining and Obstacle Course Ages 40's 50's 60's +
This singles event takes you through treetop obstacle courses and ziplines at The Adventure Park in Wheatley Heights. Aimed at people in their 40s through 60s who'd rather meet someone while clipped into a harness than swiping on their couch. The park is off Route 110, with parking on-site.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
Singles ages 20's 30's 40's Fall Twilight Ziplining @ Adventure Park
The Adventure Park's zipline and obstacle courses stay open past sunset with tree lighting for this singles meetup geared toward 20s-40s. Meet at 2:45pm at 75 Colonial Springs Road in Wheatley Heights to get harnessed up before the climbs start.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- 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!
Toni and Holly show you how to turn a vintage pickup truck planter into a fall centerpiece using fresh seasonal plants and decor. It's a collage-style workshop where you build your own arrangement to take home. Nest on Main is on Northport's Main Street with easy street parking after 6 PM.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
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