Trail Running calendar near Southington 2026-2027

Notchview Ultra in Windsor Massachusetts offers multiple timed and distance events on a 1.9 mile loop with an on-course aid station and camping options. Proceeds support the Trustees of Reservations and Baypath Humane Society.

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.

New for 2026 at Putnam Memorial State Park, The Revolution is a timed trail event run on a 1.776 mile loop that passes Revolutionary War sites. Runners choose 12 hour, 6 hour, or 3 hour formats and carry their own hydration.

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 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; 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 5.5 mile trail race at Soapstone Mountain with six steep ascents, a cupless water stop, strict parking limits and online registration capped at 50 runners; the course is technical and not recommended for novices.

A trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.

The Muddy Dash - Boston will take place in Charlton on Saturday 1 August 2026.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

An 8 hour track ultramarathon at Clapp Park in Pittsfield on a certified 0.355 mile dirt and cinder loop with chip timing, a bottle drop aid system, age group awards, and proceeds benefiting the AYJ Fund.

A 2.5 mile trail run at Wildwood State Park on August 8, 2026. The rain or shine event offers live results and free finish line photos and benefits the Friends of Wildwood State Park.

A short trail 5K through recently developed forested trails at Bridgewater Town Park on August 9, 2026. The third annual race is organized by The Bridgewater Land Trust and the Bridgewater Recreation Commission and includes participation gi..

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

A community potluck and trail run in Tolland, CT on August 15, 2026. Participants run 5K loops during an eight hour period, earn raffle tickets per loop, and receive a 50th anniversary gift after completing a loop.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K and a 5.5-mile option across mixed dirt roads and single track. On-course aid and post-race meal included; proceeds support park conservation.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.