Trail Running calendar near Forest Park 2025-2026

Take on the rugged Traprock trail at Penwood State Park with a single 17K loop or three loops for the 50K for a true trail challenge. Expect rocky, technical single track, rolling terrain and great forest views.

TARC Spring Classic at Jericho Town Forest in Weston on April 25, 2026. Run 10K, half, marathon or 50K loops on smooth scenic trails, plus a free youth fun run in a relaxed cupless event.

Celebrate trail running at the Lake Mohegan Women’s Trail Race, welcoming women and non binary runners to scenic loops in Fairfield, CT. Pick a 5K, 10K or a 4 hour loop challenge and finish with medals, podium prizes and great community vib..

Run the 52nd Jack Bristol Lake Waramaug Ultra in Kent CT on April 26 2026 for scenic, mostly flat loops around the lake with 100K, 50 Miler and 50K options. Expect stocked aid stations, finisher swag and lakeside views to inspire.

Tackle a scenic 10k trail at Leatherman's Loop in Cross River NY on April 26, 2026 for a lively, USATF sanctioned race through Reservation Road. Entry is by lottery with registration opening January 2, 2026 so mark your calendar.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

Blue 2 Blue Challenge is a demanding 50K on May 3, 2026 in New Haven, Connecticut, across rugged blue blazed trails with steep, technical climbs. Entry is by waitlist and requires a recent qualifying trail 50K, so come prepared.

Run the scenic but rugged Wapack Trail in Ashburnham, MA with 21.5, 43 or 50 mile options. Expect rocky single track, big climbs, solid aid support and a true trail challenge for experienced runners.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

Take on Ragged Mountain near Berlin CT in a last person standing race. Run a 3.11 mile loop each hour and keep finishing within the hour until only one runner completes a loop and wins.

Run the Forgotten Forest 9 hour Ultra at Roosevelt Forest in Stratford CT, a timed trail on a scenic 2.2 mile loop with roots, rocks and rolling climbs. Limited to 50 runners for an intimate, rugged day on the trails.

Take on the scenic Mine Hill Half Marathon on May 25 in Roxbury, CT, starting and finishing at Mine Hill Distillery. Enjoy a challenging climb, a fast downhill second half, a finisher medal and post race food and drinks.

Challenge yourself at Mohawk Mountain in early June 2026 with timed endurance events from 12 hour to 84 hour and distances up to 152 miles. Race solo or with Trail Buddy or Trail Family teams, tackle night sections and enjoy base support an..

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Run or ride scenic farm trails at Norbrook Farm Brewery in Colebrook CT, with options from a 5K and 10K to a 4 hour trail challenge, duathlon and competitive mountain bike races. Finishers get custom medals and entrants 21 plus receive a fr..

Take on a scenic 15.7 mile trail run on the Nipmuck Trail in Mansfield CT, following the Fenton River through woods, fields and small bridge crossings. Organized by the Shenipsit Striders, proceeds support local trail stewardship.

Run the Centurion Ultra at Roosevelt Forest in Stratford CT, a timed 100 mile trail test through classic New England terrain with a 33 hour cutoff. Limited to 50 runners, buckles await 100 mile finishers.

Join the Stonington Cross Country 5K in Pawcatuck CT on Wednesday August 12 2026 for a free community race that blends one track loop, quiet campus roads and scenic trails. A children's 1/2 mile for ages 10 and under also finishes on the sc..

Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.