Trail Running calendar near Guilford 2026-2027

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.

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.

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.

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.

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.

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 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.

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.

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.

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

The third annual Tappen Brook 5K in Bridgewater, CT, uses newly opened trails through Bridgewater Town Park with packed dirt and natural paths and views of Lake Lillinonah. Participants receive a race-day gift and top finishers earn prizes.

A community eight hour trail event of roughly 5K loops at Crandall's Park in Tolland, CT on August 15, 2026. The day includes a potluck, raffles per loop with prizes, and a 50th anniversary gift for runners who complete at least one loop.

Trail races at Fahnestock State Park near Cold Spring NY offer three distances on mixed runnable dirt roads and technical single track. Multiple aid stations and a post race meal are provided and 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.