Essex
Trail Running Calendar near Essex 2026-2027
Explore the top trail runs near Essex for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.
November 2026
A chip timed two lap cross country 5k at Stonington Vineyards with race swag, age group awards, and a charity partnership with the Connecticut Alzheimer’s Association.
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.
Eight hour loop event on 1.6 mile laps around Lake Wintergreen in Hamden CT with one aid station, food, a 50 runner limit and proceeds benefiting Doctors Without Borders.
March 2027
A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.
April 2027
Trail races at Deer Lake Outdoor Center in Killingworth CT include a timed 5 mile course and a timed 1 mile kids course on technical, well-marked trails.
May 2027
A Last Person Standing trail race on Ragged Mountain in Berlin, CT using repeat one-hour 3.11-mile loops until one runner remains; field limited to 55.
June 2027
Timed 5K trail run at Coogan Farm in Mystic CT through meadows, woods and fields, capped at 150 runners with tiered fees and youth pricing.
July 2027
A scenic 5K at Pindar Vineyards in Peconic with a post race party featuring live music, food trucks and award winning wine.