Trail Running calendar near Wilbraham 2026-2027

A trail run of roughly 3 miles through farms and vineyards at Westport Rivers Vineyard & Winery on June 7, 2026. The event includes dinner, wine, live music, and a souvenir wine glass for race participants.

A community event at Stanley Park on June 7, 2026 featuring a 5K trail run or a one mile accessible route. Proceeds support renal medullary carcinoma awareness and related programs.

A flat, non technical trail 5K at Schodack Island State Park on June 7, 2026, with kids races, post race music and a BBQ. Entry fees rise by registration period and kids races cost five dollars each.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

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.

Trail event in Dunstable, MA featuring a 5 mile loop with about 600 feet of elevation gain. Choose a single 5 mile race or a 6 hour race to run as many loops as possible.

A six hour timed trail run at Ansonia Nature Center in Connecticut, raced on repeated 1.9 mile counterclockwise singletrack loops with about 170 feet of climb per loop. Entry is limited to 69 runners and refunds are not offered.

Trail races of 50k, 30k and 10k through western Massachusetts hill towns on single track and dirt roads, held in partnership with Franklin Land Trust and featuring aid stations, first aid and locally produced awards.

A Last Human Standing trail race near Big River Management Area in West Greenwich, RI. Runners repeat the same loop each hour and must complete each lap within 60 minutes to remain in the field until only one athlete remains.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13 featuring mixed single-track and carriage-road terrain, water stations, finish-line food and music, and proceeds supporting local conservation.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

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..

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

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 event at Brooksvale Park in Hamden CT on a 4.25 mile loop with 500 feet of gain per loop. Multiple-loop options cover marathon and 50k distances and an aid station is available each loop.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit the Pawling Recreation Department.

A trail event at Red Wing Recreation Area on July 5, 2026 offering 60K, 30K and 15K on a 15k loop with mixed surfaces, aid stations, lap-support for 60K runners, and awards for top finishers.