Trail Running calendar near Ashford 2025-2026

Take on the Tower Tag Challenge at Sleeping Giant State Park, running as many 3.3 mile out and back laps as you can in 4 or 8 hour formats. Enjoy climbs to the Observation Tower while supporting the Sleeping Giant Park Association.

Join Trail Animals Running Club Winter Classic at Middlesex Fells for scenic but rugged Skyline Trail loops with 8, 32, and 40 mile options. Expect rocky climbs, limited aid, cupless racing, and a friendly sold out vibe.

Join the Frosty Forest 5K in Stratford CT on December 13 for a festive off road run through Roosevelt Forest. Run, jog, hike or walk in holiday costumes, enjoy winter trails, and support local causes.

Join the Mount Hood Nutcracker Challenge in Melrose for a festive 3.5 mile cross country race or 2 mile walk on the Mount Hood golf course. Enjoy nutcracker trophies, pasta lunch and fundraising for local families and Melrose High XC.

Join the 8th Annual Taco Trials in Rocky Hill CT: eat a taco then run a one mile loop, repeat ten times for fun and trophies. All proceeds benefit the Connecticut Forest and Park Association and the event is full with a waitlist.

Seth’s Fat Ass 50K at Forest Park in Springfield on December 20 invites runners to tackle between one 5K loop and the full ten loop 50K in a festive, low key winter setting. Enjoy scenic roads and trails, event swag and a seven hour limit.

The Dar Snowshoe Scramble will take place in Goshen on Sunday 25 January 2026. You can run 10 kilometers.

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

Join Ramsey's Run, a scenic 5k trail run through the woods in Kingston MA on Saturday March 14, 2026. This memorial event honors a Class of 2023 student and raises funds for a scholarship established by the family.

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 the scenic single track loop at Hale Reservation in Westwood, MA with 3.5 mile or 6 hour options. Trails, pond views and wood bridges await while proceeds support land conservation.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

Take on the Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT. Choose 25K or 50K two loop options over rugged, rocky singletrack with 3,000 feet of climbing; aid stations are cupless so bring your own bottle.

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

The Merrimack River Trail Race will take place in Andover on Saturday 11 April 2026. You can run 10 miles.

Hit the trails at Wompatuck State Park in Hingham MA with 5K, 5 mile and 8 hour lap options for all abilities. Expect muddy April trails, on course aid and a community feed, with registration closing April 10 and a 50 runner cap for the 8 h..

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.

Take on rugged Traprock at Penwood State Park in Bloomfield CT on April 18, 2026 with 17K one loop or 50K three loop options. Expect rolling, technical single track and rocky trails; bring your own cup for this cupless, chip timed race.

TARC Spring Classic in Weston MA on April 25, 2026 offers 10K, half, marathon and 50K trail races plus a free youth fun run on a smooth scenic 10K loop. This cupless, multi lap event fills fast so register early as parking and aid are limit..

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.