Trail Running calendar near Kingston 2025-2026

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants..

Take on the Tower Tag Challenge at Sleeping Giant State Park in Hamden, CT, and run as many 3.3 mile laps as you can in 8 hour or 4 hour formats on a scenic climb to the Observation Tower. Aid station snacks and a finisher medal await while..

Event overview The Frosty Forest 5K takes place in Roosevelt Forest in the Town of Stratford, Connecticut on Saturday, December 13, 2025. The event is a trail run over a 5K distance. Participants may wear holiday costumes during the event...

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Run Seth's Fat Ass 50K on Saturday December 20 2025 at Forest Park in Springfield MA, a friendly looped ultra offering one to ten 5K laps with a seven hour cutoff. Relaxed vibe, easy parking and race day registration welcome runners of all..

Event overview The West Rock Winter Fat Ass Extravaganza is scheduled for December 28, 2025 in Hamden, CT near Lake Wintergreen. The event is an eight-hour looped run using a 1.6-mile loop around Lake Wintergreen with about 65 feet of eleva..

Join the Frosty Fat Sass at South Mountain for scenic yet rugged trail running and hiking with a 5K or 3 and 6 hour options on rocky, rooty singletrack. This self supported fundraiser benefits the South Mountain Conservancy.

Run the Squatchy Onesiefest trail 5K on Feb 14, 2026 at Ramapo Valley, a flat scenic loop around Scarlet Oak Pond. Dress in your best onesie for a handcrafted finisher medal and costume awards in a playful community run.

Enjoy rugged woodland trails at the Mahlon Winter Donut Trail Run & Hike in Lake Hopatcong, NJ on March 1, 2026. Choose a 5 mile or 10 mile route through the Mahlon Dickerson Reservation for a true trail challenge in any weather.

Event details Squatchapple takes place on March 7, 2026 in West Orange, New Jersey at the Tulip Springs Trailhead on Cherry Lane. The event offers the following distances: 50 miler 50K 20 Miler 11 Miler Registration closes on March 6 at 1..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

Run the Morris County Empanada Trail at Central Park in late March, choose a scenic 5K or 10K over mixed terrain and hills. Finishers get a long sleeve shirt, medal and an empanada with vegetarian options.

Run scenic, rugged trails at Sleeping Giant State Park with 25K or 50K looped options featuring steep scrambles, runnable singletrack, and a climb to the Observation Tower. Proceeds support the park.

Big Bear Squatch North at Harriman State Park offers a rugged half marathon or 10K over technical trails with steep climbs and scrambling on April 4, 2026. Proceeds support the New York New Jersey Trail Conference and trail care.

Run the John Jay Community Trail Race in Cross River on Sunday April 12, 2026 for a scenic 5k through wooded, hilly school trails and a family friendly 4k walk. Kids can sprint the 200 m Jay Dash on the track and celebrate a student built c..

Join the Connecticut Traprock trail ultramarathon for community spirit and scenic challenge with 17 km and 50 km options. Held the Saturday before the Boston Marathon at Penwood State Park, this festive race draws trail runners of all level..

Squatchywaska Mountainfest offers rugged mountain trail racing with 10 mile and 25K options on technical singletrack. Limited field and charity focus make it ideal for runners who love tough trails and conservation driven events.

Wawayanda Trail Fest in Hewitt NJ offers distances from a half marathon to 100K on a scenic 26 mile loop of single track, gravel roads and rhododendron tunnels. Expect good aid support, camping and finisher awards for a true trail festival..

Join the 52nd Jack Bristol Lake Waramaug Ultra Races in Kent CT on April 26, 2026 for 50K, 50 mile or 100K loops around scenic Lake Waramaug. Expect friendly aid stations, post race food and classic New England views.

Leatherman's Loop is a scenic spring trail 10k in Cross River, NY, welcoming runners of all levels to enjoy winding park trails on April 26, 2026. Entry is by lottery and the fee includes park admission.