Trail Running calendar near Ansonia 2025-2026

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.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

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.

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.

Tackle rugged singletrack, cliffs and glacial ledges on the Shawangunk Ridge in this scenic mountain trail race offering 25K and 10 mile courses. Proceeds support Run Wild's campaign to protect Verkeerder Kill Falls.

Wawayanda Trail Fest in Hewitt New Jersey offers distances from a half marathon to a 100K through rhododendron tunnels, marsh bridges and winding single track. Aid stations and on site camping make for a friendly, challenging trail weekend.

XTERRA New Jersey at Wawayanda State Park is a weekend off road race festival with trail runs, mountain and gravel biking, triathlons and a paddle triathlon. Camp lakeside and soak up live beach music between races.

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.