Trail Running Calendar near Sturbridge 2026-2027

November 2026

Road Race Trail Run 5 km

A multi terrain 5K, a scenic 2 mile walk and a kids loop at Old Sturbridge Village on November 15, 2026 with awards and participant shirts.

Nov

21

Sa

The Hopkinton Turkey Trot

Hopkinton | 30 mi from Sturbridge

Road Race Trail Run 5 km 10 km

The Hopkinton Turkey Trot on November 21 in Hopkinton, MA offers 10K, 5K and a Little Locals 1K with proceeds supporting Family Reach and Hopkinton High School.

Nov

26

Th

Hopedale Fire & Police 5K Gobble Wobble

Hopedale | 27 mi from Sturbridge

Road Race Trail Run 5 km

An annual 5 km run and walk in Hopedale, MA that raises funds for local fire and police equipment and community programs.

March 2027

Mar

28

Su

Northern Nipmuck Trail Race

Union | 10 mi from Sturbridge

Trail Run 16 mi

A roughly 16 mile out and back trail race on the Nipmuck Trail in Union, CT with technical terrain, minimal aid stations, and parking at Bigelow Hollow State Park.

April 2027

Apr-May

30-1

Fr - Sa

Run Across CT

Thompson | 13 mi from Sturbridge

Trail Run 100 km 200 km

A 123 miles point to point ultramarathon across Connecticut from East Thompson to Southport, with trail and road sections, a 36 hour cutoff, and relay and 100K options.

June 2027

Jun

26-27

Sa - Su

New England Spartan Event Weekend

Barre | 21 mi from Sturbridge

Obstacle Run 5 km 10 km

A weekend of Spartan obstacle races on a working dairy farm in Barre MA with Sprint 5 km, Super 10 km, kids races, wooded single track, and a muddy climb.

October 2027

Oct

16

Sa

Tackle the Trail - Pomfret, CT

Pomfret | 15 mi from Sturbridge

Trail Run 6 mi 13 mi 26 mi

Trail races on the Airline Trail in Northeast Connecticut with marathon, half marathon, 10K and an up to five person marathon relay; proceeds support local students.