Long Island outdoor date nights
Sunset paddles, Caumsett sound-side trails, Sands Point bluff walks, Montauk lighthouse + Camp Hero. The LI date moves the locals do.
12 matching events
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
Editor's Pick Jones Beach Summer Concert Series — Opening Night
Jones Beach Theater kicks off the 2026 summer concert season with a headliner under the stars. Park at the West End lot by 6:30 PM — the main lot fills fast on opening night. The amphitheater holds 15,000 and the back lawn is the locals' move: cheaper, breezier, you can still hear everything. Bring a sweater; ocean wind off the Atlantic comes in cool after sundown.
- When
- Where
- Northwell Health at Jones Beach Theater, Wantagh
- Price
- TBD
Editor's Pick Jones Beach Theater — Summer Season Opener
Northwell Health at Jones Beach Theater opens its 2026 summer concert season at the iconic open-air amphitheater on the Atlantic. The 15,000-seat venue has hosted Long Island's signature summer concert moments since 1952. Tickets $45-175 depending on artist + seating tier.
- When
- Where
- Northwell Health at Jones Beach Theater, Wantagh
- Price
- TBD
Sunken Meadow State Park — Saturday Morning Trail Run
Free public trail loop, 5K and 10K options. Volunteer-organized, not a race — pace your own. Meet at the Lot 3 pavilion 8:30 AM, head out 9:00 sharp. Park admission is $8 vehicle (free if you walk in). Trail is mixed flat sand + light hills, dog-friendly on leash, kids 12+ with adult.
- When
- Where
- Sunken Meadow State Park, Kings Park
Billy Joel at Jones Beach Theater — Hometown Show
Billy Joel's annual Jones Beach Theater hometown show — the most-sacred concert ritual on the Long Island calendar. The Hicksville-raised, Cold Spring Harbor-resident Billboard Hall of Fame inductee returns to the 15,000-seat amphitheater on the Atlantic for a single summer night. The LI deep-cuts come out. The crowd is the most-LI crowd you'll see at any concert. The sunset over Bay Parkway during the opener is structurally perfect. Forty years of LI summer history in one show.
- When
- Where
- Northwell Health at Jones Beach Theater, Wantagh
- 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). This is the LI summer nightlife primer — what the East End scene actually is, how to plan around it, what to skip.
- When
- Where
- The Surf Lodge, Montauk
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
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
Shinnecock Inlet Sunset Paddle
Guided kayak + paddleboard sunset tour of Shinnecock Inlet. 90 minutes, all levels welcome (instructor on every trip), launches from Ponquogue Beach. The inlet at sunset is one of the prettiest stretches of Long Island shoreline.
- When
- Where
- Shinnecock Inlet (Ponquogue Beach launch), Hampton Bays
- Price
- TBD
Heckscher Museum — Summer Art + Cocktails Evening Series
The Heckscher Museum of Art's summer Thursday evening series — adult-focused, gallery open after-hours, light cocktails, occasional curator talks. The Huntington-village location + summer evening setting make it an easy date or small-group plan.
- When
- Where
- Heckscher Museum of Art, Huntington
- 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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