Trail Running calendar near Cheshire 2026-2027

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24 with chip timing and commemorative towels for finishers. Entry is limited to 250 runners and parking carries a 10 USD per car fee.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12-hour timed loop event in Hamden, CT on a 4.25 mile course with 500 feet of gain per loop. Options include marathon, 50K, and 50 mile attempts, with proceeds supporting the Brooksvale Gift Fund.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit the Pawling Recreation Department.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

The Red Wing Trail Challenge in Lagrangeville, NY on July 5, 2026 offers 60K, 30K and 15K trail races with substantial elevation gain. The event includes aid stations, an interactive course map, on course fuel and post race food and drinks.

Notchview Ultra in Windsor, MA runs July 10-13, 2026 on a 1.9 mile loop with multiple time and distance options, an aid station, campsite planning, event SWAG, and proceeds benefiting local organizations.

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

A new 1.776 mile loop trail race at Putnam Memorial State Park in Redding, CT, run mainly on carriage trails with some singletrack. Entry fees are listed between $50 and $80 and registration opens December 19, 2025.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

Two trail-focused races at Beartown State Forest in Great Barrington, MA: a 5-mile loop around Benedict Pond and a roughly 13.5-mile half with significant climbing and technical terrain. The event is cupless with limited parking and shuttle..

A third annual cross country event in Warwick, NY on July 25, 2026 featuring a 5k mass start race and a free 400 m kids dash where all youth finishers receive a ribbon.

A 5.5 mile trail race at Soapstone Mountain with six ascents and about 1500 feet of climb. The field is capped at 50 runners for parking reasons and online registration is required.