Long Island outdoor activities for friend groups
Sunken Meadow trail run mornings, Shinnecock paddle, Caumsett group hike, Long Beach boardwalk + brunch days — the group-of-4-6 LI outdoor playbook.
12 matching events
Editor's Pick Montauk Point Lighthouse — Summer Tours Open
Montauk Point Lighthouse (1796, second-oldest in NY State) opens its summer climbing season Memorial Weekend. Tickets $12 adults, $4 kids 6-15, under-6 free. The 110-foot climb to the top is one of LI's signature summer experiences — and the State Park around the lighthouse has the most-dramatic LI scenery.
- When
- Where
- Montauk Point Lighthouse, Montauk
- Price
- TBD
Editor's Pick Old Westbury Gardens — Summer Open Season
Old Westbury Gardens is one of Long Island's most underappreciated cultural treasures — a 200-acre English landscape estate with formal gardens, the Phipps mansion, and weekly summer concerts on the West Pond. Family-friendly, golden-hour-perfect, and the kind of LI experience that makes out-of-state visitors reconsider Long Island.
- When
- Where
- Old Westbury Gardens, Old Westbury
- Price
- TBD
Editor's Pick Long Beach Boardwalk Concert Series — Memorial Weekend Kickoff
Long Beach's 2026 summer Thursday-night boardwalk concert series opens Memorial Weekend with a free concert at the National Boulevard bandshell. The 2.2-mile boardwalk is at its summer-evening best — sunset over the Atlantic, free LIRR-accessible parking-not-required, and the West End bar strip 4 blocks back for post-show drinks.
- When
- Where
- Long Beach Boardwalk — National Bandshell, Long Beach
Sayville Memorial Weekend Classic Car Show
Sayville Village's annual Memorial Saturday classic car show fills downtown Main Street with 150+ pre-1990s cars — muscle cars, woodies, hot rods, classic Mustangs, vintage Cadillacs, a working 1962 Checker cab from the Sayville Cab Company that's been doing the show since 1958. Free admission, family-friendly, walkable from the LIRR Sayville stop, and the unofficial South Shore summer-kickoff scene that locals plan their Memorial Weekend Saturdays around.
- When
- Where
- Downtown Sayville, Sayville
Tanger Outlets Deer Park — Summer Kickoff Weekend
Memorial Day weekend extended hours, food trucks at the central plaza, kids' bounce houses at the south end Saturday + Sunday 11-3, and the season's first sidewalk sale across most stores. Free entry, free parking. Skip the south lot — north lot is closer to where the food trucks set up.
- When
- Where
- Tanger Outlets Deer Park, Deer Park
Heckscher Museum Spring Open House
Free admission to the permanent collection plus a curator-led tour of the spring exhibition. The Hudson River School room is the highlight — most visitors blow past it for the contemporary wing. Free parking, family-friendly, indoor. A solid rainy-Sunday option.
- When
- Where
- Heckscher Museum of Art, Huntington
Long Island Children's Museum — Toddler Tuesday
Weekly Tuesday morning program for ages 18 months to 3 years. Toddler-pace activities, music circle 10:30, free play in the toddler-only space until noon. Included with general admission. The 9:30 opening slot is the quietest; the museum starts to fill by 11.
- When
- Where
- Long Island Children's Museum, Garden City
- Price
- TBD
Sayville Farmers Market — Saturday Mornings
Best South Shore farmers market. 30+ local farms + bakers, free parking, 8 AM start. Get there by 9 to beat the after-yoga crowd. Coffee at Common Ground first, market browse 9-11, breakfast sandwich from the market itself.
- When
- Where
- Downtown Sayville, Sayville
Patchogue Alive After Five — Opening Night
Downtown Patchogue's summer Friday-night street festival opens June 5 and runs every Friday through August. Main Street shuts down 5-10 PM. Four music stages, 30+ food vendors, beer gardens at three corners, family activities at Roe Park, and the highest Friday-evening foot traffic of any South Shore downtown. 8,000+ attendees on opening night. Free admission. The South Shore's signature summer ritual.
- When
- Where
- Downtown Patchogue (Main Street), Patchogue
Editor's Pick Old Westbury Gardens — Family Picnic Sundays
Old Westbury Gardens' summer Sunday picnic concerts on the West Pond lawn. Family-pricing ($15 adult, $10 ages 4-15), classical + swing acts rotating weekly, abundant lawn space for blankets, the Children's Garden + maze 3 minutes from the music. The LI family Sunday-afternoon default.
- When
- Where
- Old Westbury Gardens, Old Westbury
- Price
- TBD
Maker Faire Long Island 2026 — The Greatest Show & Tell on Earth
Maker Faire Long Island's annual STEM-meets-art-meets-family festival lands at Stony Brook University's Student Activities Center for a full Saturday in June. 200+ exhibits across robotics, 3D printing, electronics, traditional crafts, and DIY science demos. Kid-perfect — engineered for ages 6-13 attention spans. The LI family-festival anchor that explains why Long Island raises so many engineers.
- When
- Where
- Stony Brook University, Student Activities Center, Stony Brook
- 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
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