Trail Running calendar near Sterling 2026-2027

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A limited-field 6 hour trail ultra at Roosevelt Forest in Stratford CT with a 50K option on a 2.3 mile loop through roots, rocks and rolling hills.

A roughly 16 mile out and back on the Nipmuck Trail in Union CT with minimal aid stations, blue blazes, and proceeds supporting local trail stewardship.

A point to point 123 mile ultramarathon across Connecticut on April 3, 2027, featuring trail and road sections, aid stations, five intermediate cutoffs and a 36 hour limit.

Trail races on a 25K loop at Sleeping Giant State Park featuring technical singletrack, steep rock scrambles, and an optional second loop for the 50K.

An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.

The Merrimack River Trail Race will take place in Andover on Saturday 10 April 2027. You can run 10 miles.

Trail event in Bloomfield CT with 17K and 50K loop courses featuring technical Metacomet Trail single track and rocky forest terrain.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A looped hill endurance event in Cumberland Rhode Island where participants run or hike as many laps as possible within a 12 hour period. The top male and female who cover the greatest distance are named King and Queen of the Hill.

Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.

The inaugural F.I.T. 50k in Cumberland, Rhode Island is a 50k trail ultramarathon with equal parts smooth non technical and moderately technical terrain. The event includes a generous cutoff time and a $65 registration fee.

Timed 5K trail run at Coogan Farm in Mystic CT through meadows, woods and fields, capped at 150 runners with tiered fees and youth pricing.

A 20 miles single loop hike through Wompatuck State Park near Boston on June 5, 2027 with aid stations, a finisher medal and a personalized certificate.

An iterated loop endurance race in West Greenwich RI where runners repeat a 3.8 mile loop with 450 ft of climb and must complete each loop within 60 minutes until only one runner remains ready to continue.

A two day Spartan obstacle event at Carter & Stevens Farm near Barre MA featuring Sprint 5 km, Super 10 km and kids races across wooded trails and open pastures.