Trail Running calendar near Farmington 2026-2027

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Trail races at Monastery Trails in Cumberland, RI on March 14, 2027 offer distances from a 1 mile kids run to a 100K 12 hour ultra. Team ultra entries and a multilap 5 hour option are available and all finishers receive a medal.

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A six hour trail ultra at Roosevelt Forest in Stratford, CT on March 20, 2027, offering a 50K option on a 2.3 mile loop of roots, rocks and rolling hills, with a capped field of 50 entrants and on-course food and hydration.

A 5K trail run and free kiddie fun run at Bethpage State Park featuring soft, scenic trails, on-site refreshments and a virtual option with a one-week window to log results.

A trail run in Union, CT on March 28, 2027 offered as a 16 Miler along the Nipmuck Trail through Yale-Myers Forest. Organized by Shenipsit Striders with limited parking, no race day registration, and minimal aid stations.

A community 5K run/walk at Bethpage State Park with a free kiddie run and a virtual option, held on grassy polo fields and winding soft trails. Live results, finish-line photos, and proceeds benefit the Never Stop Running Foundation.

A 123.2 mile point to point ultramarathon across Connecticut from East Thompson to Southport with mixed trail and road terrain, aid stations and medical support, a 36 hour limit, plus 100K and relay options.

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY. The route uses sand, dirt roads, hard packed trails and pavement, supports Last Chance Animal Rescue, and is dog friendly with leash rules.

An obstacle course race in Cumberland, Rhode Island featuring a 3.2 miles course with about 1,000 feet elevation, multiple wave formats including elite and age group competition, multilap sessions, and a 12 hours ultra option.

Trail races of 50K and 17K at Penwood State Park in Bloomfield, CT on April 17, 2027. The loop course features rocky single track on the Metacomet Trail and a nine hour cutoff for the 50K.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.