Essex
Trail Running Calendar near Essex 2026-2027
Explore the top trail runs near Essex for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A community 5K in Bolton, CT on 10/17/2026 along the Hop River rails to trails, with a $30 entry donated to Project Purple to support pancreatic cancer awareness.
Trail 5K and a kids one mile fun race on a 33 acre campus in Middlefield CT with breakfast treats and finisher medals.
An off‑road 50k through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.
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 Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.
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 race on 1.6 mile laps around Lake Wintergreen in Hamden, CT, with one aid station, food provided, a 50 runner limit, and proceeds to 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 with an approx 5 mile course, about 500 ft of elevation gain, and a timed 1 mile kids run.
May 2027
Last Person Standing trail race on Ragged Mountain near Berlin CT with repeated one hour 3.11 mile loops until a single 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.