Trail Running calendar near Brookfield 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..

Join the Tower Tag Challenge at Sleeping Giant State Park for a scenic timed loop to the Observation Tower, with 4 hour and 8 hour options. Run repeated 3.3 mile laps on a smooth carriage road with aid station support and finisher medals.

Run a timed 50 miles or 50 kilometers in Prospect Park on a scenic looped course near Lincoln Road. Community aid with Skratch Labs hydration and a potluck style aid station keeps you fueled across the day.

Tough Cookie 8K at Sunken Meadow State Park offers scenic cliffside views of the Long Island Sound, festive cookie stops and a post race cookie fest. All paces welcome and proceeds support local charities.

Take on SRC Presents: A Backyard Ultra on Dec 13 to 14, 2025 at Blydenburgh Park, where runners do 4.167 mile laps each hour until one remains. A 1 Lapper runs alongside and proceeds benefit the Long Island Greenbelt Trail Conference.

Join the NJ Trail Series SOMO Winter 2 on Saturday December 13 in South Orange for scenic looped trail races through South Mountain Reservation. Choose 5K, 10K or 13.1 mile and enjoy hilly single track, a giveaway and day of registration.

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.

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.

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.

Run the Last Supper 100k in Roxbury NJ on Dec 27, starting at Horseshoe Lake. Choose solo or relay teams up to 10 and tackle scenic trails and lakeside roads for a winter ultramarathon adventure.

Join the West Rock Winter Fat Ass in Hamden CT on Dec 28, 2025 for eight hour loop fun around Lake Wintergreen. Run repeated 1.6 mile laps with aid and snacks in a 50 runner field while supporting Make a Wish and the American Cancer Society..

Join the Frosty Fat Sass on Jan 31 in West Orange for a rugged trail fat ass fundraiser supporting South Mountain Conservancy. Choose a 5K, or timed 3 hour or 6 hour loop challenge with a rucking division and enjoy technical winter trails.

Try snowshoe racing at Mountain Creek on January 31, 2026 with a scenic ridge 5k or a relaxed one mile finish. Ride the lift to the top, bring your own snowshoes, and enjoy a fun winter run for all abilities.

Dress in your best onesie and tackle scenic trails at Squatchy Onesiefest in Ramapo Valley. Choose a fun 1.6 mile loop or a two lap 5K, enjoy trail support and a handcrafted finisher medal while supporting the NY NJ Trail Conference.

Febapple Frozen invites you to a winter trail challenge at South Mountain Reservation on Feb 21, 2026, with 10 mile loops and distances from 10 miles to 50 miles. Aid stations, official timing, event swag and awards for top finishers add ra..

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.

Squatchapple in West Orange, NJ on March 7, 2026 offers 11, 20, 50K and 50 mile trail races over three scenic loops in South Mountain. Expect rugged singletrack, big climbs, handcrafted wood finisher medals and a fun trail festival vibe.

Take on the Livingston Oval Ultra in Livingston NJ on March 7, 2026 with 1, 3, 6 or new 12 hour timed lap options on a fast, flat USATF certified course. Friendly aid stations, custom awards and a loop made for high mileage await.

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Run under the pines at the Enchanted Forest Ultra Run in Roosevelt Forest, Stratford CT, offering a 6 hour or 50K timed trail challenge on rugged trails. Only 50 entries, costumes welcome, with pizza, aid stations and medals.