67 Things to do near Middle Island, NY 11953
first prev 1 2 3 4 next lastShowing results within 50 miles Distance miles of Middle Island, NY 11953, USA City, Zip, or Address
Prosser Pines
Middle Island, New York
1.1 miles SMajestic white pines tower in hushed silence over this Long Island 'forest cathedral,' where sweet pine scent fills the air and a strong breeze creates an almost mystical mood.
Cross-country Ski
True Skatepark
Port Jefferson Station, New York
6.7 miles NWA street-course-focused skate park in Port Jefferson Station with quarterpipes, banks, a pyramid, and flat bars — pads required, membership fee, and a skate shop right on site.
Skateboard
Sans Souci Preserve
Sayville, New York
10.9 miles SWMostly singletrack trails in Sayville with a few hills and tight wooden bridges over swamps in the back section — new signage on the way.
Mountain Bike
Hidden Pond Park
Hauppauge, New York
12.6 miles WDecent climbs, some technical singletrack, and shared terrain with hikers and horses make this beginner-to-intermediate mountain bike trail at Hidden Pond Park worth the trip near Hauppauge, New York.
Mountain Bike
Meadowlark Park
Fort Salonga, New York
18.9 miles WTight, technical singletrack with lots of logs and log-hopping — a still-developing trail in a small wooded enclave surrounded by suburbia.
Mountain Bike
Edgewood Preserve
Deer Park, New York
20.6 miles WMostly wide singletrack and doubletrack on a flat beginner loop, with newer intermediate-to-advanced diamond sections adding steep climbs and off-camber challenge.
Mountain Bike
Jennings Beach Skatepark
Fairfield, Connecticut
23.6 miles NWA 16-foot mini ramp spines into a street course with a big pyramid, ledges, quarter pipes, flatbanks, and grind boxes — a well-equipped YMCA skatepark in Fairfield requiring pads and a small fee.
Skateboard
Fairfield University
Fairfield, Connecticut
25.1 miles NWOpen hilly terrain with mowed fairways, mature trees, a beautiful lake hole, and challenging slope baskets — guests welcome on this private Connecticut university course.
Disc Golf
Compo Beach Skatepark
Westport, Connecticut
26.6 miles NWAn outdoor street course with quarterpipes, a fly box, a funky quarter-bowl, spines, launch ramps, and every type of rail imaginable at this Westport, Connecticut skatepark right at Compo Beach.
Skateboard
High Plains Disc Golf Course
Orange, Connecticut
27.3 miles NBuilt entirely on a shale rock mountain with unique topography, great views, tight shots, elevation, casual streams, and an OB log wall — dual tees add variety on 5 holes.
Disc Golf
Manetto Hills
Woodbury, New York
27.6 miles WA short, advanced-beginner singletrack surrounded by suburbia in Woodbury, NY — tight switchbacks, some technical climbs, and easy bailing access make it a great local gem.
Mountain Bike
Park City Disc Golf Course at Veteran's Park
Bridgeport, Connecticut
27.7 miles NWChallenging and scenic with elevated tees, expansive fairways, fast greens, rock outcroppings, open meadows, small streams, and mature forest.
Disc Golf
Caumsett State Park
Lloyd Harbor, New York
27.8 miles WA multi-trail network in Lloyd Harbor at Caumsett State Park — all two-way routes including fire roads, single track, and double track for cyclists of varied abilities.
Mountain Bike
Trail View State Park
Woodbury, New York
28.0 miles WA 6-to-8-mile south-running trail from Woodbury toward Bethpage State Park — mostly easy, with a technical stretch between the two parkways and a few road crossings.
Mountain Bike
Stony Creek Quarry Preserve
Branford, Connecticut
28.7 miles NA network of trails at Stony Creek Quarry Preserve in Branford, primarily marked with painted or reflective colored blazes — a solid mountain biking destination in Connecticut.
Mountain Bike
Bethpage State Park
Bethpage, New York
28.8 miles WA beginner-to-intermediate trail network in Bethpage with mixed singletrack and fire roads — marked trails that are manageable for most riders with connections to the paved Massapequa path.
Mountain Bike
Pequonnock River Valley State Park / Trumbull
Trumbull, Connecticut
28.9 miles NWTrumbull is Connecticut's premier mountain bike destination — a valley park with XC singletrack, drops from 2 to 20 feet, a 30-foot roller called the Green Monster, and four marked trails.
Mountain Bike
Brickyard
Bethpage, New York
28.9 miles WRutty, highly technical singletrack on the eastern side of the park — more demanding than the western half and a solid challenge for skilled riders.
Mountain Bike
Oyster Shell Park
Norwalk, Connecticut
29.0 miles NWA short free disc golf course tucked between I-95 and Norwalk Harbor, with roads and water as out-of-bounds — bring the map, no tee signs.
Disc Golf
Supply Ponds
Branford, Connecticut
29.6 miles NSteep hills, rocks, and at least one known fallen tree across the trail — a short but physical mountain bike ride that keeps you alert.
Mountain Bike
