Trail Running calendar near Tolland 2026-2027

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

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.

A lap-based 100-mile trail event at Roosevelt Forest in Stratford, CT, with a 33-hour cutoff and a field limited to 50 runners. The course features New England single and double track, a single pavilion aid station, and pacer rules.

A 12 hour timed event at Brooksvale Park in Hamden CT on a 4.25 mile loop with 500 feet of gain per loop. Multiple-loop options cover marathon and 50k distances and an aid station is available each loop.

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.

A trail event at Red Wing Recreation Area on July 5, 2026 offering 60K, 30K and 15K on a 15k loop with mixed surfaces, aid stations, lap-support for 60K runners, and awards for top finishers.

Notchview Ultra runs July 10-13, 2026 at Notchview in Windsor, MA using a 1.9 mile loop with an aid station and bathrooms. Multiple timed and distance formats are offered, with campsite options and beneficiaries including local conservation..

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.

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

Experience a historic trail run at Connecticut's Putnam Memorial State Park. Choose between 3, 6, or 12 hour options on a 1.776 mile loop that passes through former Revolutionary War encampments.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.

A 12 hour trail event in Lawrence Woods, Medford, MA featuring an about 5 mile loop that stays in the woods, a minimal aid station, and the option for participants to set up personal support near the start area.

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..

The Soapstone Assault will take place in Somers on Sunday 26 July 2026. You can run 6 miles.

Experience the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Anchor Down Ultra presents a series of timed ultra-marathons on the coast of Rhode Island. Runners can choose a 6, 12, or 24 hour challenge within Colt State Park.