Trail Running calendar near Wolcott 2026-2027

A free community trail event in Farmington offering shoe demos and short runs on local trails. Options include about 5 km, 1.7 mile, and 1 mile routes, with snacks and drinks afterwards.

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

A six hour looped trail run at Ansonia Nature Center on roughly 1.9 mile counterclockwise singletrack loops with about 170 feet of gain per loop. Field capped at 69 runners; no crews or pacers; early signup includes a shirt and swag.

A low key trail event in Ashfield, MA on June 13, 2026 that showcases local trails and preserved lands. It offers 50 km, 30 km and 10 km distances and raises funds for the Franklin Land Trust.

A loop based endurance race near Big River Management Area in West Greenwich, RI where runners must complete each circuit within 60 minutes to continue; laps repeat at one hour intervals until only one runner remains.

A community 5K at Van Cortlandt Park on June 13, 2026 with in-person and virtual options plus a kid’s mile; proceeds support local charities and all finishers receive a medal.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A community 5K and untimed 1-mile family walk at Camp Edey in Bayport supporting Girl Scouts of Suffolk County. The day includes family activities, finisher medals, event shirts, and awards while raising funds for scholarships and programs.

A mixed-surface 5 km race and one-mile fun run at Hampshire Regional High School in Westhampton on June 13, 2026. The 5 km combines paved roads and wooded trails; awards, refreshments, restrooms and parking are provided.

Trail races in Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new in-park 5K, with varied terrain, marked courses, and proceeds benefiting Connecticut trail stewardship groups.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A 53-mile Catskills ultramarathon with about 15,000 feet of climb, technical trail sections, nine aid stations and a 23-hour cutoff. The point-to-point route starts near Windham and finishes in downtown Phoenicia.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

Operation WOODSTOCK on June 20, 2026 in Elka Park, NY is a 14.5 mile load bearing event with 5,210 ft elevation gain and a 20 lb dry pack. Entry is listed at $105 plus $7.35 tax.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

A loop-format trail run in Adams, MA, offering one to three loops and a separate 5 km meadow option on varied singletrack and hiking trails; proceeds support Thunderbolt Ski Runners trail stewardship around Greylock Glen and Mt. Greylock.

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.

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.