Trail Running calendar near Burlington 2026-2027

A spring trail event at Muscoot Farm featuring a *5 mile* race plus two kids races by age group; participants receive Farm Bucks for the farmers market and shirts are available by pre-order. Service dogs only; no other dogs permitted.

Run Like The Wind 5K in Ellenville winds along the base of the Shawangunks and a scenic stretch on the Rail Trail. Finish in Aroma Thyme Bistro's garden with beer, wine and food while supporting food pantries and youth scholarships.

A new Soapstone Mountain Half Marathon debuts in 2026 alongside the Jerry Stage 6K. Both are trail races in Shenipsit Forest starting at Reddington Rock Riding Club, organized by the Shenipsit Striders with proceeds to trail stewardship gro..

Annual May trail races on the Ashuwillticook Rail Trail including a marathon, half marathon, 8K and a free kids Mo Mile, with proceeds supporting trail maintenance in Pittsfield and event perks for participants.

A *3.5 mile* trail run/walk at Woodtick Recreation Area in Wolcott, CT on May 17, 2026. Proceeds support the Wolcott Cross Country Teams and participants receive a free entry to the CT Food Truck Battles Festival.

Run or walk the Never Stop Running Foundation Long Island Lemonade Trail 5K on May 23, 2026 at Blydenburgh County Park, with an in person or virtual option. Free Kiddie Dash and proceeds benefit the foundation.

A road half marathon in Roxbury, Connecticut on May 24, 2026 that features mixed pavement and dirt sections, notable climbs including a 250 foot gain near the halfway point, and a post race celebration at Mine Hill Distillery.

A multi day endurance series at Mohawk Mountain in Connecticut offering solo and team trail events from 15 to 152+ miles with timed formats up to 84 hours. Tenting, support stations, and personalized bibs and medals are provided.

A point-to-point ultramarathon on the New England Trail offering 112-mile and 50-mile options to Guilford. Entrants must make a donation to the Connecticut Forest and Parks Association and arrange their own crew and navigation.

A scenic 10 km run starting and finishing at historic Rockwood Hall in Rockefeller State Park Preserve. The event includes a separate kids race for ages 12 and under and directs proceeds to carriage road maintenance.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

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

A six hour trail run at Ansonia Nature Center on June 13, 2026, run as counterclockwise loops of about 1.9 miles on moderately technical singletrack with roughly 170 feet of gain per loop. Entry is limited to 69 runners.

A trail running event at Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new 5K course entirely inside the park. Proceeds support Connecticut trail stewardship groups.

Manitou's Revenge is a 53 mile ultramarathon across the Catskills with about 15,000 ft of climbing, rocky and steep terrain, limited aid stations, and long self supported stretches between services.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Twelve hour timed run on a 4.25 mile loop with about 500 feet of gain per loop in Hamden, CT. Options include marathon via six loops, 50K via eight loops, and a 50 mile target; proceeds support the Brooksvale Gift Fund.

Trail racing at Red Wing Recreation Area with 15K, 30K, and 60K options on a 15k loop featuring varied terrain, aid stations, lap support for 60K runners, and post race food and drinks.

Notchview Ultra in Windsor MA runs multiple timed events on a 1.9 mile loop with an on-course aid station, campsite options, and beneficiaries including the Trustees of Reservations and Baypath Humane Society.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.