Trail Running calendar near Burlington 2026-2027

Trail races in Upton State Forest include a 10.5K loop and a 13.1 mile half marathon run as two laps. Aid stations are spaced about every 3 miles and post race offerings include fire pits, hot soup and hot chocolate.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half and marathon on technical single track with significant elevation. Finisher medals, awards and a cash bonus for fast half marathoners.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

A trail half marathon in Roosevelt Forest featuring eight laps of a 1.64 mile wooded loop with roots, rocks, and rolling terrain. The event includes a book drive, costume prizes, event swag, and podium awards for top finishers.

A trail event at YMCA Camp Sloper on November 21, 2026, offering a 400 minute timed loop option and a two mile two lap race, with chip timing, a central aid station, and proceeds supporting local organizations.

A community Thanksgiving event featuring a 3.5 mile run and walk around Scoville Reservoir in Wolcott CT, with multiple start waves, post race yoga for participants, finisher medals, volunteers supporting refreshments, and proceeds to EndoF..

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.

Repeat a 3.3 mile out and back up the Tower Trail to the Observation Tower at Sleeping Giant. Runners choose a four hour or eight hour format, carry their own hydration, and complete as many laps as they can within the time limit.

A forest trail 5K in Roosevelt Forest, Stratford, CT on December 19, 2026, where participants may run, jog, hike, or walk in costume. Awards go to the three fastest men and women and all finishers receive a commemorative item.

A onesie-themed 5K at Ramapo Valley County Reservation on February 14, 2027, run on a flat scenic loop around Scarlet Oak Pond. The event is capped at 200 participants, has no cutoff, offers adaptive support, and includes a finisher medal.

A 5K trail run and walk at Bethpage State Park with a free kiddie run and virtual option. On-course hydration, post-race refreshments, age-group recognition, and proceeds support the Never Stop Running Foundation.

A spring trail out-and-back on the Nipmuck Trail near Bigelow Hollow, advertised as 16 miles on technical, blazed singletrack with minimal aid and limited parking; proceeds support local trail stewardship.

A community 5K run and free kiddie run on the soft trails of Bethpage State Park, supporting the Never Stop Running Foundation. The event includes in-person and virtual options, refreshments, bib mailing, and age-group recognition.

A 123-mile point-to-point ultramarathon across Connecticut combining roughly 57 miles of trails with paved backroads, a 36-hour cutoff, relay options, aid stations, on-course medical support, and finish awards including a buckle and event s..

A mountain trail event at Harriman State Park on April 3, 2027 offering a half marathon, a 10K and a 10K ruck on rugged technical trails with significant elevation gain. Entry is capped at 400 and proceeds support trail maintenance.

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 5K trail run and walk at Blydenburgh County Park in Smithtown, NY with mixed trail surfaces, dog friendly rules, on site amenities, live results and proceeds supporting Last Chance Animal Rescue.

A women only trail race at Lake Mohegan in Fairfield CT offering 5K, 10K and a 4 hour loop option. The event features finisher medals, podium awards, post race food and supports a local non profit.

Two trail events, 25K (about 17 miles) and 10 miles, on technical singletrack and crushed gravel around the Shawangunk Ridge near Ellenville NY. Routes feature steep climbs, two aid stations, a six hour cutoff and a 150 runner cap.

Squatchywaska Mountainfest in the Shawangunk Ridge on April 24, 2027 features a technical 25K and a 10 mile lollipop course with steep climbs, rocky singletrack, two aid stations, and a six hour cutoff.