Trail Running calendar near Pomfret 2025-2026

Brave winter trails at Hale Education in Westwood, MA for the TARCtic Frozen Yeti on Feb 7 to 8, 2026, a scenic tri loop course that returns to the lodge. Choose a 30 hour ultra or a single 15 mile lap and test your winter trail skills.

The Ramsey's Run will take place in Kingston on Saturday 14 March 2026. You can run 5 kilometers.

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

TARC To Hale and Back features a scenic 3.5 mile loop through woods and shoreline with roots, rocks and a few modest hills. Pick a timed 6 hour challenge or the single loop and enjoy a friendly aid station and strong volunteer support.

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.

Event details The Sleeping Giant Trail Runs take place March 29, 2026 at Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT. The event offers these distances: 25K 50K (two loops of the 25K loop) Registration closes March 27. Entry f..

Run Across CT 123 is a scenic 123 mile ultramarathon across Connecticut from East Thompson to Southport, weaving through forest trails and backroads. Enter as a timed solo or relay team and challenge yourself to finish within the 36 hour cu..

The Merrimack River Trail Race is a USATF-sanctioned 10-mile out-and-back trail run held in Andover, Massachusetts, starting from the DoubleTree by Hilton Hotel parking lot. The course features water stations at miles 2, 4, and 8, with a mi..

Event overview Spring Fever takes place Saturday, April 11, 2026, at Wompatuck State Park campgrounds in Hingham, MA (204 Union St). Registration closes Friday, April 10 at 11:59 PM ET. The event offers the following distances: 5K 5M 8-Hou..

Run scenic singletrack at Penwood State Park in the Traprock 17 km and 50 km Ultramarathon, a friendly community race with short and long course options. Race day is the Saturday before the Boston Marathon.

Event overview The TARC Spring Classic is a trail race held at Jericho Town Forest in Weston, Massachusetts (start/finish: 292 Concord Road). Distances offered are 10K, Half Marathon, Marathon, and 50K, plus a free youth fun run and discoun..

Join the 52nd Jack Bristol Lake Waramaug Ultra Races in Kent CT on April 26, 2026 for 50K, 50 mile or 100K loops around scenic Lake Waramaug. Expect friendly aid stations, post race food and classic New England views.

Event overview The Blue 2 Blue Challenge is a 50K trail event in New Haven, CT on May 3, 2026. It is held as an out-and-back that starts at West Rock Playground and follows the blue-blazed trail system. Organizers report a slightly over 80%..

The Dandelion Dash will take place in Hadley on Sunday 3 May 2026. You can run 5 kilometers.

TARC Wapack and Back in Ashburnham MA on May 9 2026 features 21.5, 43 and 50 mile runs along the rugged Wapack Trail with big elevation and wide views to Boston and surrounding ranges. Expect technical terrain and backcountry challenge.

Forgotten Forest 9-Hour Ultra : May 16, 2026 The Forgotten Forest 9-Hour Ultra takes place at Roosevelt Forest in Stratford, CT (GPS address: 700 Peters Lane). The event is limited to 50 participants. Registration is final; there are no ref..

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those..

IronHike Series Spring '26 at Mohawk Mountain June 4 to 7, 2026 offers solo and team FlexRelay options with repeat climbs by day and night to amass mountain level elevation. Expect on course support and finisher medals.

The Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run will take place in Fitzwilliam on Saturday 6 June 2026. You can run 5 miles.