Deep River
Trail Running Calendar near Deep River 2026-2027
Explore the top trail runs near Deep River for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Trail event at Alice Newton Street Park in Woodbridge CT offering a 4 mile trail run and a 2 mile woodland walk, with shirts, refreshments and awards.
Trail races at YMCA Camp Sloper featuring a 400 minute multi-loop event and a 4 mile two-lap race, with chip timing, an aid station, and limited fields.
Inaugural Stride for the Knights 5K at Southington High School features a wooded cross-country course with a track finish, a kids fun run, and awards from Fleet Feet.
Off-road 5 km and 5 mile run plus a 5 km ruck in South Glastonbury on November 28, with a kids fun run and a post-event chili, s'mores and brewery beverages.
December 2026
Timed trail event at Sleeping Giant State Park with repeated 3.3 mile out and back laps on the Tower Trail and 4 hour or 8 hour options.
A ten-loop, one mile per loop event in Deep River, CT totaling 10 miles, with taco rules, medals per loop, trophies, and proceeds to the Connecticut Forest and Park Association.
An 8 hour loop event at Lake Wintergreen in Hamden CT with 1.6 mile loops, one aid station, on course snacks and a 50 runner limit. Proceeds support Doctors Without Borders.
March 2027
A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027 with a cross country grass course, wine pour, race shirt, cup, and medal.
April 2027
Timed trail races at Deer Lake Outdoor Center in Killingworth CT include a roughly 5 mile course with about 500 ft of elevation gain and a new timed 1 mile kids run.
May 2027
Twelve hour trail endurance run on a scenic 5K loop at Chatfield Hollow State Park with individual and relay options and a 100 runner limit.
A Last Person Standing trail race on Ragged Mountain near Berlin CT with roughly 3.11 mile loops repeated hourly until one runner remains.
June 2027
A 5K trail and obstacle run on the 400-acre Gaylord Specialty Healthcare campus in Wallingford, CT supporting adaptive sports and hospital fundraising.
July 2027
A scenic 5K at Pindar Vineyards in Peconic with a post race party featuring live music, food trucks and award winning wine.