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 visits Pan Am Museum Art + Wine/Cheese Live ♫ Nassau
Wine, cheese, live music, and Pan Am artifacts at the Cradle of Aviation—this singles mixer actually gives you things to talk about beyond the usual small talk. Browse the museum exhibits between conversations. Free parking at the museum off Lindbergh Boulevard.
- When
- Where
- Cradle of Aviation Museum, Garden City
- Price
- See ticket page
Editor's Pick 7 in Heaven Speed Dating for Long Island Singles Ages 34-48 Hicksville
Speed dating at Vitality Lounge in Hicksville for singles in their late 30s and 40s—women 34-47, men 36-48. Seven-minute rotations starting at 6:30pm on a Saturday night. South Broadway has street parking and a few lots within walking distance.
- When
- Where
- Vitality Lounge, Hicksville
- Price
- See ticket page
Editor's Pick 7 in Heaven Singles Speed Dating Age C 44-59 Lindenhurst Village
Speed dating for singles 44-59 at The Green Door in Lindenhurst. Seven-minute rotations give you enough time to actually get a read on someone without the endless messaging back and forth. Sunday afternoon timing means you can grab dinner after at one of Wellwood's spots if things click.
- When
- Where
- The Green Door, Lindenhurst
- 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
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 Speed Dating Healthcare & Educators Speed Dating Age A 25-38
Speed dating exclusively for healthcare workers and educators ages 25-38. If you're tired of explaining shift work or why you can't text back during class, this crowd gets it. Simplay in Hauppauge hosts, right off Vets Highway.
- When
- Where
- Simplay, Hauppauge
- Price
- See ticket page
Singles Band Jam Sunset Boat Cruise Dinner / Dance- All Ages
A singles-only sunset cruise out of Babylon with a live band, dinner, and dancing on The Moon Chaser. All ages welcome, departing from the Ocean Parkway dock at 7pm. Expect a bay cruise with a party vibe—this isn't a quiet harbor tour.
- When
- Where
- The Moon Chaser, Babylon
- Price
- See ticket page
Long Island Speed Dating for Singles Age 30s/40s ♥ Rockville New York
Pre-Dating brings structured speed dating to Churchills in RVC—you'll meet up to 12 people in one night, all in their 30s and 40s. South Park Avenue is walkable from the LIRR if you're coming from the city or other towns.
- When
- Where
- Churchills, Rockville Centre
- Price
- See ticket page
7 in Heaven Singles Zip-lining and Obstacle Course Ages 40's 50's 60's +
Aerial adventure course for singles 40s-60s+ at the Adventure Park in Wheatley Heights. The ziplines and tree obstacles are legitimately challenging without being crazy intense—ground harnesses mean you're clipped in the whole time. Starts earlier than the younger crowd's session, wrapping before sunset.
- 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
Ziplines and aerial obstacle courses light up at dusk for this singles meetup (20s-40s) in Wheatley Heights. Way less awkward than sitting across from someone at a bar, and you'll find out pretty quickly who keeps their cool under pressure. Sessions run about two hours.
- When
- Where
- The Adventure Park at Long Island, Wheatley Heights
- Price
- See ticket page
7 in Heaven Singles Speed Dating Age C+ 50-65 Roslyn
Speed dating for singles 50-65 at Mim's in Roslyn Heights, where you'll rotate through seven-minute conversations instead of swiping through profiles. The format keeps things moving—you'll meet everyone in the room, then let the organizers know who you'd like to see again. Parking lot is right behind the restaurant on Roslyn Road.
- When
- Where
- Mim's Restaurant, Roslyn Heights
- Price
- See ticket page
7 in Heaven Speed Dating for Long Island Singles Ages 40-55 Hauppauge
Speed dating night at Simplay in Hauppauge for singles in their 40s and early 50s—women 40-53, men 42-55. You'll cycle through short one-on-one conversations with everyone there, then exchange contact info with mutual matches afterward. Commerce Drive has ample parking right at the venue.
- When
- Where
- Simplay, Hauppauge
- 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 walk you through collaging a vintage pickup truck planter into a fall centerpiece you can use through Thanksgiving. You'll work with real materials to create a finished piece, not a kit to take home and finish later. Nest on Main is on Northport's Main Street with street parking nearby.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
NEW! Lemon Topiary Making Class - Hosted by All Set By Gabrielle
All Set By Gabrielle teaches you how to build a faux lemon topiary in a chinoiserie ginger jar from the ground up. This is hands-on crafting, not a demo—you'll leave Nest on Main with a finished piece. Northport's Main Street has metered parking and plenty of cafes if you want to grab lunch before or after.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
Browse by category
Looking for free events? See free events →