Trail Running calendar near Simsbury 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.

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 classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

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..

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

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..

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 fast, point-to-point half marathon descending from Slingerlands to the Hudson River in Albany. The course features paved rail trails and offers amenities like live tracking, gear check, and a post-race celebration. A free shuttle bus mana..

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 5K race winds through Heckscher Farm and forest trails at the Stamford Museum and Nature Center. Children can join a short fun run past friendly farm animals. The event offers a unique running experience surrounded by nature.

A community trail event in Irvington on April 12, 2026 featuring a 5k trail run and a 0.6 mile kids 1K for ages 10 and under, with a portion of proceeds supporting the Irvington Bulldog Booster Club.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

The Traprock 50 features a rugged 50K and a 17K trail race on the rocky, rolling loops of Penwood State Park. It's a cupless event with chip timing, organized by volunteers to benefit local conservation groups. Runners should be prepared fo..

The final Conquer the Trail Race is a 7.5 km run on the flat Croton Aqueduct Trail. This special edition supports Mercy University's Mav Market and celebrates the school's 75th anniversary. The event offers awards, raffles, and free parking..

Run or walk a 5K through the orchards of Brooklyn Cider House. Registration includes a cider glass, donut, and finisher medal. The event is open to all ages and welcomes dogs and strollers.

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

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..