Trail Running Calendar Connecticut 2026-2027

A road half marathon around Mine Hill Distillery in Roxbury CT featuring mixed paved and dirt roads, a long climb in the first half and a mostly downhill return. Three aid stations support a cupless hydration policy and finishers receive a..

A timed 5K trail race at Coogan Farm in Mystic, running through meadows, woods, and fields, with limited entry, tiered fees, an awards ceremony, and opportunities to meet Nature Center animal ambassadors.

A weekly Tuesday evening cross country series at Waveny Park with varied distances and formats, including predicted time races, relays, handicaps, a luminaria finish, and age-graded awards.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

A trail festival at Norbrook Farm Brewery with running races, a run and bike duathlon, and mountain bike events on farm road and single track trails. Participants 21 and over receive one free beer ticket and there are finisher medals and aw..

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

Six hours of looped trail running at Ansonia Nature Center on Saturday June 13, 2026. The course uses roughly 1.9 mile singletrack laps with about 170 feet of elevation gain per lap and is limited to 69 runners.

Trail races at Mansfield Hollow State Park: a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K trail loop. Proceeds support Connecticut trail stewardship groups.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12-hour timed loop event in Hamden, CT on a 4.25 mile course with 500 feet of gain per loop. Options include marathon, 50K, and 50 mile attempts, with proceeds supporting the Brooksvale Gift Fund.

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.

New for 2026 at Putnam Memorial State Park, The Revolution is a timed trail event run on a 1.776 mile loop that passes Revolutionary War sites. Runners choose 12 hour, 6 hour, or 3 hour formats and carry their own hydration.

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

A 5.5 mile trail race at Soapstone Mountain with six ascents and about 1500 feet of climb. The field is capped at 50 runners for parking reasons and online registration is required.