Trail Running calendar near Roxbury 2025-2026

Join Pond Fest Winter Trail Runs and Snowshoe at Chenango Valley State Park during the Pond Festival for scenic looped trails from 10k to 50k and a kids race. Crowds and aid at the start and finish make for a lively, supportive day.

Hit the trails at the YETI OR NOT Snowshoe Invasion at Mountain Creek on January 31, 2026. Ride the lift to the top for a scenic 5k or untimed last mile welcoming runners, walkers and first time snowshoers. Bring your own snowshoes.

Try the Fire and Ice Winter Run at Gilbert Lake State Park for scenic snowy loops on forest, gravel and road with options for 10K, 25K or 50K and snowshoes welcome. Warm aid, coffee and fireplaces at the Briggs cabin and proceeds support a..

Tackle technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

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.

Join the 10K Run for the Osprey at Lacawac Sanctuary on Sunday April 19 2026, with a scenic 10K trail run and a family friendly 5K walk supporting sanctuary conservation. Expect wooded trails, osprey sightings, and awards for top finishers.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 serves up technical singletrack on the Shawangunk Ridge with 25K and 10 mile options, big climbs and sweeping Catskill views. This rugged trail event also supports protection of..

Wawayanda Trail Fest brings spring trail running to Wawayanda State Park NJ with rhododendron tunnels, marsh bridges and scenic single track. Distances include a new 100K plus 50 mile, 50K and half marathon, with aid stations and on site ca..

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

Recharge your trail legs with a small group spring camp in Oliverea, NY, in the Catskills. Tackle technical scrambles and big climbs while getting on trail coaching and mental performance work to sharpen your skills and confidence.

IronHike Series Spring 26 takes place June 4 to 7 at Mohawk Mountain, CT, with solo and team endurance options from 15 to 152 miles. This non competitive FlexRelay invites crews to self manage pacing, rest and night trekking.

Challenge Plattekill Mountain on June 7, 2026 in Roxbury NY with a brutal 6.5 mile climb up 3500 ft or a thrilling 5k that opens with a big climb and finishes fast downhill. Awards and finisher swag await.

The Norbrook Farm Brewery Trail Festival will take place in Colebrook on Saturday 13 June 2026. You can run between 5 and 4 hours.

Manitou’s Revenge is a rugged 53 mile ultramarathon through the Catskill Mountains on June 20, 2026, featuring roughly 15,000 ft of climbing and technical, often remote terrain. Expect limited aid and a true test of endurance and trail skil..

Notchview Ultra invites runners July 10 to 13, 2026 in Windsor, MA, offering formats from 100.7 miles down to 6 hour on a scenic 1.9 mile loop. Enjoy frequent aid, camping, swag, and proceeds supporting local conservation.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Tackle scenic ski area trails at Belleayre Mountain in Climb It For Climate, a community trail race offering challenging 25K and shorter 8K options. Proceeds support The Catskill Center and registration includes a zero carbon travel offset.