Trail Running calendar near Upton 2026-2027

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.

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.

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.

Part of the Grit Series, this Dublin NH trail event offers a 10K and a half marathon with substantial elevation gain and views of Mount Monadnock. Registration runs from May 3 to June 6, 2026.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

Muddy Princess Boston is a women only 5K obstacle mud run at Kimball Farm in Haverhill on June 21, 2026. The course has 18 plus obstacles and is open to women aged 7 and up who may run, jog or walk.

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.

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.

Notchview Ultra in Windsor, MA runs July 10-13, 2026 on a 1.9 mile loop with multiple time and distance options, an aid station, campsite planning, event SWAG, and proceeds benefiting local organizations.

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.

A 12K trail race on the Blue Hills Skyline Trail with about 2,300 feet of climbing, rocky steep terrain, and minimal aid. The route follows Skyline blazes from the Blue Hills Ski Area parking lot and requires participants to carry 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 12-hour loop event in Lawrence Woods within the Middlesex Fells Reservation near Medford, MA. The course is an approximately five mile loop with a minimal aid station; participants commonly set up personal spots near the start and aid are..

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.

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

A trail run in Bedford, New Hampshire on July 30, 2026 offering separate 5 km categories for adults, youth, and kids. Online registration is available and participants can add donations or purchase merchandise to support the Rotary Club of..

Muddy Dash in Charlton on August 1, 2026 is a few miles of muddy obstacles with mud pits up to waist deep, Value and VIP registration options, free spectator access and packet pick up at the venue the day before.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.