Trail Running calendar near Old Lyme 2026-2027

A 3 x 2 mile cross country relay at Sunken Meadow State Park in Kings Park, NY, marking the 47th running of the event. The program includes a youth division, a costume contest with prizes, post race refreshments and multiple age categories.

Looped hill races at Sunken Meadow State Park where the most distance in a three hour loop crowns the King and Queen, and a separate one hour event crowns the Prince and Princess.

This 5K trail run at Bethpage State Park offers a scenic, mostly flat course through the park's soft trails. Participants receive a themed shirt and can enjoy post-race refreshments, including a free beer for those 21+. The event supports t..

Run or walk a 5K through the scenic Osprey's Dominion Vineyards in Peconic. Registration includes a wine glass, a medal that works as a wine stopper, and a pour of wine. The event is open to all ages and even welcomes leashed dogs.

A low key out and back trail race in Union, Connecticut, following the Nipmuck Trail for about 16 miles of technical, hilly terrain with minimal aid stations and a cap of 100 runners. Proceeds support local trail stewardship.

Course and Distances The Sleeping Giant Trail Runs take place at Sleeping Giant State Park in Hamden, Connecticut. The event offers two distances: 25 km: A single loop with over 3,000 feet of vertical gain. 50 km: Two loops of the 25 km co..

Run the perimeter of Heckscher State Park on smooth trails. Choose a 7-mile or 14-mile loop for a cupless, manually timed race. All finishers get a wooden medallion and a bucket hat.

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

A 5K run and walk at Bethpage State Park on April 4, 2026 with a free kiddie run and a virtual 5K window, trail terrain, on-site amenities, and proceeds benefiting the Never Stop Running Foundation.

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique *6.55-mile* quarter marathon on the scenic paved trails of West Hartford Reservoir. This small event, limited to 150 participants, features two loops and professional timing. Race day registration is available with a $25 cash f..

A *5K* trail run/walk through Blydenburgh County Park on April 11, 2026 with in-person and virtual options, on-site refreshments and hydration, dog-friendly rules, and proceeds supporting Last Chance Animal Rescue.

A community trail event in Cross River, NY on April 12, 2026 featuring a 5k trail race, a 4k walk that skips part of the hill loop, and a 200 meter kids dash on the track.

A spring event at the Stamford Museum and Nature Center on April 12 2026 featuring a scenic 5K through farm and woodland and a 0.3 mile kids run past farm animals. Proceeds support the museum and nature center.

A point to point trail event on the Long Island Greenbelt Trail with 50K and 25K options, fully stocked aid stations, required two hours of volunteer trail work, and a finish at Heckscher State Park with a shirt and finisher award.

Trail races at Penwood State Park offer a 50K (three loops) and a 17K (one loop) over primarily single-track and double-track terrain, with a nine hour cutoff for the 50K. The event is cupless and organized by the CT Trailmixers.

Two trail races on April 19, 2026 at Brookhaven State Park in Wading River: a 15K and a 4 mile course through single track, fire trails, sandy sections and woodlands, run as a cupless event with age group awards and charity support.

The Lake Mohegan Women's Trail Race is a women's-only trail event in Fairfield, CT. Runners can choose from a 5K, 10K, or a 4-hour challenge on the runnable trails around the lake. The event aims to welcome both newcomers and experienced tr..

A three-race 5K series at White Barn Farm in Wrentham, MA, held across spring, summer and fall. Each trail event reflects seasonal conditions and a Grand Prix combines results for awards and a gift bag at the final race.

The Radish Rambler 5k is a trail run, walk, or hike through scenic conservation land and White Barn Farm in Wrentham. Held on April 25, 2026, it kicks off the farm's season and the Farm to Trail Series. Proceeds support local agriculture an..