Trail Running calendar near Hauppauge 2025-2026

Hit the trails at NJ Trail Series SOMO Winter 3 in South Orange with 5K, 10K or a half marathon on looped trails through South Mountain Reservation. Enjoy rolling hills, single track and fire roads, friendly aid stations and a giveaway at t..

Join the Frosty Fat Sass on Jan 31 in West Orange for a rugged trail fat ass fundraiser supporting South Mountain Conservancy. Choose a 5K, or timed 3 hour or 6 hour loop challenge with a rucking division and enjoy technical winter trails.

Try snowshoe racing at Mountain Creek on January 31, 2026 with a scenic ridge 5k or a relaxed one mile finish. Ride the lift to the top, bring your own snowshoes, and enjoy a fun winter run for all abilities.

Celebrate Valentine's Day in a cozy onesie at the Squatchy Onesiefest 5K in Mahwah Feb 14. Enjoy a flat scenic trail loop around Scarlet Oak Pond with a fun run option, handcrafted finisher medal and a limited field for a festive race vibe.

Febapple Frozen invites you to a winter trail challenge at South Mountain Reservation on Feb 21, 2026, with 10 mile loops and distances from 10 miles to 50 miles. Aid stations, official timing, event swag and awards for top finishers add ra..

Enjoy rugged woodland trails at the Mahlon Winter Donut Trail Run & Hike in Lake Hopatcong, NJ on March 1, 2026. Choose a 5 mile or 10 mile route through the Mahlon Dickerson Reservation for a true trail challenge in any weather.

Squatchapple in West Orange, NJ on March 7, 2026 offers 11, 20, 50K and 50 mile trail races over three scenic loops in South Mountain. Expect rugged singletrack, big climbs, handcrafted wood finisher medals and a fun trail festival vibe.

Run the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park on March 8 2026 for a scenic trail 5K across grassy polo fields and winding soft trails. Family friendly with a kids run, virtual race and refreshments.

Enjoy a scenic 5K around Osprey's Dominion Vineyards in Peconic, NY on a two lap cross country style course for runners and walkers. Finishers get a shirt, bottle stopper medal, shatterproof wine glass and a wine pour.

Tackle the Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT on March 29, 2026 with 25K and 50K options across rugged singletrack and big climbs. Expect steep scrambles, more than 3,000 feet of gain per loop, cupless aid s..

Join the Morris County Empanada Trail on March 29 in Morris Plains NJ with 5K and 10K runs over scenic mixed terrain. Entry includes a long sleeve shirt, finisher medal and an empanada with proceeds benefiting the Arthritis Foundation.

Run rugged trails at Big Bear Squatch North in Harriman State Park on April 4, 2026 with half marathon, 10K and ruck divisions. Expect steep climbs, scrambling terrain and sweeping Hudson Valley and NYC skyline views.

Join the Bunny Trail 5K at Bethpage State Park for a family friendly run starting on a grassy polo field and winding onto scenic soft trails. In person and virtual entries plus a free kiddie run support the Never Stop Running Foundation.

Find your pace at the Spring SOMO Timed Trail Races in April at South Mountain Reservation, NJ, with options from a single 3K loop to 6 Hour timed runs. Enjoy a scenic 1.88 mile loop of single track, pavement and fire road.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Join Run for the Rescue on April 11, 2026 for a scenic 5K through Blydenburgh County Park with on site and virtual options. Tackle varied trails, enjoy post race refreshments, and support Last Chance Animal Rescue.

Join the John Jay Community Trail Race on Sunday April 12 2026 in Cross River NY for a scenic 5k on wooded trails, a 4k community walk and a 200 meter kids dash on the track. Early preregistered participants get race shirts.

Run the Shore2Shore on April 18, 2026 in East Islip, NY, a scenic point to point along the Long Island Greenbelt Trail from Sunken Meadow to Heckscher State Park. Choose 25K or 50K with well stocked aid stations and finish swag.

Tackle rugged trails at Penwood State Park in Bloomfield CT with the Traprock race, offering a single loop 17K or a three loop 50K on scenic, rocky Metacomet Trail. Hosted by CT Trailmixers, this cupless trail run supports local land trusts..

Celebrate spring at the Brooklyn Cider House Spiked Apple 5K on April 19 in New Paltz, a scenic two lap run through vineyards and orchards. Enjoy a cider pour, fresh donut, finisher medal and commemorative shirt.