Long Island food + drink date nights
North Fork wine tasting Saturdays, brewery yards in summer, restaurant week prix-fixe weeknights, Heckscher Museum art + cocktails Thursdays.
11 matching events
Farmingdale Spring Bar Crawl
A bar crawl through downtown Farmingdale starting at Dark Horse Tavern on Main Street. Teams compete in bar games as they move between stops, with prizes and drink specials throughout. Main Street has metered parking and municipal lots within a block.
- When
- Where
- Dark Horse Tavern, Farmingdale
- Price
- TBD
North Fork Wine Trail — Saturday Tasting Hours
20+ North Fork vineyards open for tasting Saturday 11 AM – 6 PM. We'd start at Macari (best Cab Franc on the island), grab lunch at Lenz's outdoor garden, swing through Bedell, end at Pellegrini for sunset. Designated driver, ride share, or the Wine Tour Bus — please don't drive yourself between tastings.
- When
- Where
- North Fork Wine Trail (20+ vineyards), Cutchogue
- Price
- TBD
The Cookery — Seasonal Cooking Classes Long Island
The Cookery (Northport) runs hands-on cooking classes weekly — Italian, French, Mediterranean, seasonal seafood. 2-3 hour sessions, you eat what you cook, BYOB. The locals' move for a date night or small-group celebration that doesn't feel like 'going out to dinner.'
- When
- Where
- The Cookery, Northport
- Price
- TBD
North Meets South Festival
Great South Bay Brewery hosts an outdoor festival with craft beer, food vendors, local artisans, and live music. Early bird general admission is $10, and the Drexel Drive location in Bay Shore puts you close to the waterfront if you want to walk around before or after.
- When
- Where
- Great South Bay Brewery, Bay Shore
- Price
- TBD
Governor's Comedy Club — Saturday Standup
Governor's is the dedicated comedy club on Long Island. Levittown location, every weekend brings 3 to 5 acts (a feature, a middle, a headliner) in classic 90-minute comedy-club format. Touring acts mix with regional + NYC comics workshopping new material.
- When
- Where
- Governor's Comedy Club, Levittown
- Price
- TBD
Famous Food Festival - June 19-21 2026 - Deer Park, NY "Taste The World"
More than 120 vendors serving international food set up at Tanger Outlets for a three-day festival with live music and rides. The Deer Park location means easy parking and access off the LIE.
- When
- Where
- Tanger Outlets - Deer Park, Deer Park
- Price
- TBD
Long Island Restaurant Week — Spring + Fall Editions
Long Island Restaurant Week runs twice a year — 11 days in late April and late October — with 175+ participating restaurants offering 3-course prix-fixe menus at $30, $40, $50 price points. The locals' move to try the destination restaurants without committing to a full-price weekend night.
- When
- Where
- 175+ Long Island Restaurants, Long Island
- Price
- TBD
Long Island Comedy Festival — Three Nights, Three Venues
Long Island Comedy Festival is a three-night October showcase across Governor's Comedy Club Levittown, The Paramount Huntington, and the Suffolk Theater Riverhead. 12+ touring acts including former SNL writers, late-night regulars, and rising NYC comics. The locals' move for serious comedy in a single weekend.
- When
- Where
- Multiple Venues (Governor's + Paramount + Suffolk Theater), Long Island
- Price
- TBD
Surf Lodge Tuesday — DJ Sunset Set in Montauk
Montauk's Surf Lodge is the East End summer nightlife reference standard — outdoor deck overlooking Fort Pond, DJ sets at sunset Tuesday through Sunday, a scene that has launched a thousand magazine think-pieces. The Tuesday slot is the locals' move (Wednesday and Friday are the chaos).
- When
- Where
- The Surf Lodge, Montauk
Long Island Brewery Trail — Summer Saturday Tour
Long Island has 20+ active craft breweries — Greenport Brewing, Blue Point in Patchogue, Long Ireland in Riverhead, Six Harbors in Huntington, Brickhouse in Patchogue, and the East End cluster. The Brewery Trail passport gets you a tasting + free pint at each participating brewery. Designated drivers + Uber budget required.
- When
- Where
- Long Island Brewery Trail (20+ breweries), Long Island
- Price
- TBD
West End Friday Night — Long Beach Bar Strip
The Long Beach West End strip — three blocks of bars, restaurants, and outdoor seating — comes alive every Friday + Saturday summer night. Minus5 Ice Lounge, Sloppy Tuna, Joe's, and the boardwalk-adjacent rooftops are the regulars. LIRR direct from Penn means car-free city escape.
- When
- Where
- Long Beach West End, Long Beach
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