Trail Running calendar near Rocky Point 2025-2026

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..

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..

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.

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 the John Jay Community Trail Race in Cross River NY for a scenic hilly 5k, family friendly 4k walk and Kids Jay Dash on the track. Finish on the contest field, enjoy community built trails and snag a race shirt by registering early.

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 women and non binary runners at the Lake Mohegan Women’s Trail Race on April 25, 2026 with scenic trails around the lake. Pick a 5K, 10K or a 4 hour loop to challenge yourself and earn a finisher medal.

Run the 52nd Jack Bristol Lake Waramaug Ultra in Kent CT on April 26 2026 for scenic, mostly flat loops around the lake with 100K, 50 Miler and 50K options. Expect stocked aid stations, finisher swag and lakeside views to inspire.

Tackle a scenic 10k trail at Leatherman's Loop in Cross River NY on April 26, 2026 for a lively, USATF sanctioned race through Reservation Road. Entry is by lottery with registration opening January 2, 2026 so mark your calendar.

Challenge yourself at VCP50k, a scenic but rugged 50k ultramarathon in the Bronx on May 2, 2026. Ten loops of classic cross country trail bring rocks, roots and rolling climbs with stocked aid stations, a custom finisher singlet and post ra..

Tackle rugged, technical single track with steep climbs and exposed sections at Breakneck Point in Beacon NY, choosing 14.5 mile or 26.4 mile distances with big elevation gain. Entry includes post race food, a Patagonia Cap Cool shirt, and..

Blue 2 Blue Challenge is a demanding 50K on May 3, 2026 in New Haven, Connecticut, across rugged blue blazed trails with steep, technical climbs. Entry is by waitlist and requires a recent qualifying trail 50K, so come prepared.

Run The Farm is a scenic 5 miles trail race at Muscoot Farm in Katonah, NY, with kids races and a festive farm market finish. Enjoy trails, local treats, and community spirit in spring and fall editions.

C'mon Armageddon brings technical trail running to Norvin Green Park in West Milford, NJ with 50K, 10 mile and 5 mile routes through boulder fields, river crossings and steep climbs. Expect rugged singletrack and a raw mountain challenge.