Trail Running calendar near Guilford 2026-2027

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.

A seaside set of timed ultra-marathon events at Colt State Park in Bristol, Rhode Island, offering 6 hour, 12 hour, and 24 hour formats with separate entry periods and fees.

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.

A scenic 2.5 mile trail run and walk at Wildwood State Park on August 8, 2026, with live results, free finish line photos, and personalized bibs for early registrants. Proceeds benefit the Friends of Wildwood State Park.

The 3rd Annual Tappen Brook 5K in Bridgewater, CT on August 9, 2026 runs on the new Bridgewater Town Park trails through woodlands near Lake Lillinonah, with participation gifts and awards for top finishers.

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.

An evening 3.6 mile trail run through Forest Park in Queens that visits 543 acres of wooded trails with rolling hills. After the run a festival area has music, vendors, food trucks and awards with participant tees provided.

An eight-hour trail event in Tolland, Connecticut where participants run repeated ~5K loops from Crandall's Pavilion. The day includes music, a potluck with pancakes and burgers, and proceeds that support Connecticut trail stewardship.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026 with 50K, 25K and a 5.5 mile option, multiple aid stations, a post race meal and proceeds supporting 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.

Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont, MA features a 4.2 mile loop through woods, fields and an apple orchard. Participants run as many 4.2 mile laps as they choose within six hours and receive award..

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A multi event ultramarathon in West Greenwich, Rhode Island featuring a repeated 10 mile loop with desert, pavement and trail sections. Chip timed events include aid stations, a finisher sweatshirt and a buckle for 100 mile finishers.

A 50K looped trail race in Forest Park, Queens on August 29, 2026. Runners complete twelve 2.5 mile laps on the Orange Trail with about 300 ft of climb per lap and an 8 hour cutoff.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

A family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

An unsupported, end-to-end group run of about 56 miles along the Farmington Canal Heritage Trail from West Suffield to New Haven, organized as a fundraiser for Mental Health Connecticut with a 14 hour completion limit and required self-supp..

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.