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
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 visits Pan Am Museum Art + Wine/Cheese Live ♫ Nassau
Singles gather at the Cradle of Aviation Museum for a Pan Am-themed evening with wine, cheese, live music, and access to the exhibits. The event starts at 5 PM, so you'll get golden hour over the museum grounds in Garden City. Parking is free in the museum lot 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 at Vitality Lounge on South Broadway in Hicksville—women 34-47, men 36-48. You'll cycle through seven-minute conversations with other singles instead of burning another Saturday swiping. Check the organizer's site for exact pricing and what time to arrive.
- 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 Village, a casual bar on Wellwood Avenue. Expect structured rounds of quick conversations designed to make in-person connections. Street parking along Wellwood or the municipal lot behind Sunrise Highway.
- When
- Where
- The Green Door, Lindenhurst
- 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 Speed Dating Healthcare & Educators Speed Dating Age A 25-38
This speed dating night at Simplay in Hauppauge is specifically for healthcare workers and educators ages 25-38. The organizers are banking on shared professional values to spark connections. Simplay is off the Nesconset Highway in a commerce park with plenty of lot parking.
- When
- Where
- Simplay, Hauppauge
- Price
- See ticket page
Singles Band Jam Sunset Boat Cruise Dinner / Dance- All Ages
This singles-only boat cruise departs from Babylon at 7 PM for an evening of dinner, dancing, and live music on the water. The Moon Chaser leaves from the marina on Ocean Parkway—open to all ages, so expect a wide range of crowds. Parking available at the marina lot.
- When
- Where
- The Moon Chaser, Babylon
- Price
- See ticket page
Long Island Speed Dating for Singles Age 30s/40s ♥ Rockville New York
Pre-Dating runs structured speed dating at Churchills in RVC—you'll meet up to 12 people in your age range (30s and 40s for this one) through timed conversations, then submit your matches afterward. South Park Avenue has municipal lots within a block if street parking's tight.
- 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 +
Singles in their 40s through 60s can tackle ziplines and treetop obstacles at The Adventure Park's aerial course in Wheatley Heights. It's a different approach to meeting people—less small talk over drinks, more figuring out who can handle a 30-foot platform. Park is off Colonial Springs Road with its own lot.
- 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
Singles in their 20s through 40s tackle the zipline and treetop obstacle course at Adventure Park as the sun sets and the course lights come on. This is the outdoor aerial park off Colonial Springs in Wheatley Heights, just south of the LIE. Expect a physically active crowd and bring closed-toe shoes.
- 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 the 50-65 crowd at Mim's in Roslyn Heights—actual face-to-face conversations instead of swiping through profiles. The setup gives you a few minutes with each person before rotating, so you'll meet a dozen potential matches in one evening. Mim's is on Roslyn Road with parking in back.
- 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 in Hauppauge for singles 40-55, with women 40-53 and men 42-55 rotating through quick conversations at Simplay on Commerce Drive. Same concept as the apps but you get actual voice, eye contact, and gut reaction. Easier to spot chemistry—or lack of it—in person.
- 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
NEW! Lemon Topiary Making Class - Hosted by All Set By Gabrielle
All Set By Gabrielle is showing you how to build a faux lemon topiary in a chinoiserie ginger jar—the kind of coastal prep decor you see all over the North Shore. You'll make the entire thing from scratch and take it home. This one's at Nest on Main in Northport on a Sunday afternoon.
- When
- Where
- Nest on Main, Northport
- Price
- See ticket page
7 in Heaven Singles Speed Dating Age 40-55 Roslyn
Speed dating for singles 40-55 at Mim's in Roslyn Heights. Seven-minute conversations rotate through the evening—standard format, straightforward setup. The restaurant's on Roslyn Road near the LIRR station if you're taking the train in.
- When
- Where
- Mim's Restaurant, Roslyn Heights
- Price
- See ticket page
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