Trail Running calendar near Charlestown 2025-2026

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.

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..

TARCtic Frozen Yeti brings winter trail racing to Hale Education in Westwood, MA on Feb 7 and 8, 2026. Choose a rugged 30 hour endurance challenge or a scenic 15 mile loop and tackle snowy trails under starlight.

Join Ramsey's Run, a scenic 5k trail run through the woods in Kingston MA on Saturday March 14, 2026. This memorial event honors a Class of 2023 student and raises funds for a scholarship established by the family.

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.

Run TARC To Hale and Back on March 21, 2026 at Hale Education in Westwood MA, a scenic 3.5 mile trail loop with woods, ponds and boardwalks. Limited spots often sell out so register early.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Take on rugged singletrack, a steep headwall scramble and 3,000 feet of climbing at Sleeping Giant Trail Runs, with 25K and 50K options. At Sleeping Giant State Park in Hamden CT on March 29, proceeds benefit the park and finishers get meda..

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

Spring Fever brings scenic early spring trail racing to Wompatuck State Park in Hingham on April 11, with 5K, 5 mile, and an 8 hour multi lap challenge. Expect muddy trails, on course aid, and a friendly campground finish line vibe.

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.

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.

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 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..