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 memorabilia at the Cradle of Aviation Museum in Garden City. This singles mixer lets you wander the exhibits between conversations, which beats standing around a bar. Free museum parking off Charles 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 night at Vitality Lounge in Hicksville for singles 34-48. Seven-minute rotations let you meet a dozen or more people in one evening without the back-and-forth of apps. Starts at 6:30pm on South Broadway near the LIRR station.
- 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 a quick read on compatibility without the endless texting. Street parking on Wellwood fills up fast on Sundays, so budget extra time.
- 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 night specifically for healthcare workers and educators ages 25-38. If you're tired of explaining your job to people who check out after two minutes, this field-specific mixer at Simplay in Hauppauge might actually deliver some common ground.
- When
- Where
- Simplay, Hauppauge
- Price
- See ticket page
Singles Band Jam Sunset Boat Cruise Dinner / Dance- All Ages
The Moon Chaser cruises out of Babylon at 7pm for a singles-only sunset sail with a live band, dinner, and dancing. All ages welcome, though you must be single to board. The boat leaves from the dock at 3500 Ocean Parkway—arrive 20 minutes early for check-in.
- 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 +
Zipline and treetop obstacle course session for singles 40s-60s+ at Adventure Park. Earlier start time at 3:45 PM means you'll tackle the aerial courses in full daylight. Harness fitting takes about 15 minutes, so show up early.
- 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
Twilight ziplining and aerial obstacle courses for singles in their 20s through 40s at Adventure Park in Wheatley Heights. The tree-lit courses stay open past dusk, and honestly, navigating rope bridges together is a better icebreaker than small talk over drinks.
- 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 at Mim's for singles 50-65 who'd rather meet people over drinks than through an app. Seven quick dates, one evening, actual conversation. Roslyn Heights has street parking plus a municipal lot off Powerhouse 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 at Simplay in Hauppauge for singles roughly 40-55 (women 40-53, men 42-55). Seven mini-dates in one night, face-to-face instead of endless texting. Commerce Drive is right off the LIE with free lot parking.
- 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 show you how to collage and fill a vintage pick-up truck planter into a fall centerpiece. You'll leave with a finished piece ready for your table. Evening class means easier parking on Northport's Main Street than weekend workshops.
- 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 walks you through building a faux lemon topiary in a chinoiserie ginger jar from the ground up. It's at Nest on Main in Northport, right on walkable Main Street where you can grab lunch before or after. Expect to leave with a finished piece that looks way more expensive than whatever this costs.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
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