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.
11 matching events
Caumsett State Park — Fall Hike + Private Beach Day
Caumsett is the Lloyd Harbor peninsula state park reached by a 1.5-mile walk through mature forest to a private (no parking, no crowds) beach on Long Island Sound. Free, family-friendly, dog-leash-allowed. Fall foliage peak is mid-October. The 'private beach' aspect is real — most visitors don't make the walk.
- When
- Where
- Caumsett State Park, Lloyd Harbor
Sands Point Preserve — Fall Mansion Tours + Trail Walks
Sands Point Preserve is the Port Washington-adjacent peninsula with three Gilded Age mansions, 5 miles of trails, and Long Island Sound shoreline. Fall mansion tours run Friday-Sunday September through November. The Hempstead House mansion is famously the supposed inspiration for Gatsby's mansion.
- When
- Where
- Sands Point Preserve, Sands Point
- Price
- See ticket page
Editor's Pick Islanders vs. Rangers — Battle of New York
The Islanders host the Rangers at UBS Arena in Belmont — the regular-season opener of the most-watched rivalry in NYC-area pro sports. UBS Arena is the modernized 17,000-seat home of the Islanders since 2021. Plan extra time for parking + the Belmont Park access road traffic on game nights.
- When
- Where
- UBS Arena, Belmont Park
- Price
- See ticket page
Long Beach Marathon + Half — Boardwalk Sunday
Long Beach's annual fall marathon + half-marathon along the 2.2-mile boardwalk + neighborhood streets. The boardwalk loop is genuinely one of the prettiest urban race courses in metro NYC. Spectator-friendly — most of the course is visible from the boardwalk.
- When
- Where
- Long Beach Boardwalk, Long Beach
- 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
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
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
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
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
- See ticket page
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
- 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
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