Trail Running calendar near Brewster 2025-2026

The Wayland / HFC Striders XC Festival, held in Wayland, Massachusetts, is a vibrant cross-country running event featuring three youth 3K races and two open 5K races for adults. The course winds through scenic fields and wooded trails, offe..

ORR Alumni Trail Race is a 5k run/walk held in Marion, Massachusetts, on the Washburn Park cross-country course. The event invites supporters to back the Old Rochester Regional cross country and track and field teams, with all proceeds dire..

Join United We Move at Fall River Bioreserve on Oct 18 for scenic runs, rides and walks across trails and gravel roads. Enjoy live music, family fun and a food and drink ticket included with registration.

Carry your chosen load and tackle the 2.5 mile out and back on the WWII Veterans Memorial Trail in Mansfield, aiming to complete as many laps as you can in a six hour window. Each lap adds to your pound mile score for overall placement.

The Ravenswood Trail Race, part of the North Shore Trail Series, takes place in Ravenswood Park, featuring a scenic course through single track and carriage roads amid peak fall foliage. This classic fall trail race offers a challenging and..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods,..

Pumpkin Pacer 5k @ White Barn Farm is a 5K off-road trail run/walk held at White Barn Farm, 431 South Street, Wrentham, MA 02093. It’s the final race in the Farm To Trail 5K Series and is open to all ages and abilities. The course weaves th..

Womp Romp on October 25 at Wompatuck State Park in Hingham MA features a scenic 10 mile and a rugged 50K across single track, wide trails and some pavement. Expect mud, friendly aid stations, runnable loops and standout finisher swag.

Enjoy crisp fall trails at the Powisset Farm Trail Run in Dover on October 26, 2025, with distances from 1.5 to 8.3 miles through Powisset Farm and Noanet Woodlands. Family friendly fun, cider donuts and post race food make it a great autum..

The TARC Stone Cat Trail Festival is a renowned trail running event held annually in Ipswich, Massachusetts, within Willowdale State Forest. Offering a variety of distances including 10K, half marathon, marathon, 50-mile, and 100K races, pl..

Join the TARCkey Trot, a six hour timed challenge at Wright Locke Farm on November 15, 2025, running multiple 5K trail loops over rocky rollers. Tackle as many laps as you like while supporting land conservation.

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a rugged outdoor event held in Berkley, Massachusetts, honoring military personnel, first responders, and their K-9 partners. Participants can run, ruck with weighted packs, or walk a challen..

Turkeywacker 5K is a Thanksgiving morning trail run held in Wrentham, Massachusetts, at the William Rice Recreation Complex (54 Emerald Street). Now in its ninth year, the scenic 5K course winds through the complex’s trail system, welcoming..

Event details The TARC Winter Classic takes place Saturday, December 6, 2025, at Middlesex Fells Reservation in Stoneham, Massachusetts. Distances offered are: 8 mile 32 mile 40 mile Online registration closes at the beginning of race wee..

The Mount Hood Nutcracker Challenge is an annual cross-country running event held at the Mount Hood Golf Club in Melrose, Massachusetts. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating f..

Brave winter trails at Hale Education in Westwood, MA for the TARCtic Frozen Yeti on Feb 7 to 8, 2026, a scenic tri loop course that returns to the lodge. Choose a 30 hour ultra or a single 15 mile lap and test your winter trail skills.

Event overview Spring Fever takes place Saturday, April 11, 2026, at Wompatuck State Park campgrounds in Hingham, MA (204 Union St). Registration closes Friday, April 10 at 11:59 PM ET. The event offers the following distances: 5K 5M 8-Hou..

Event overview The TARC Spring Classic is a trail race held at Jericho Town Forest in Weston, Massachusetts (start/finish: 292 Concord Road). Distances offered are 10K, Half Marathon, Marathon, and 50K, plus a free youth fun run and discoun..

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those..