Trail Running calendar near Sterling 2026-2027

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

A stadium stair-climb at Gillette Stadium where participants run, walk, or roll through about 5,184 steps in support of Homes For Our Troops. The event offers team and wheelchair waves, optional fundraising, and spectator registration.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

A stadium obstacle race weekend at Fenway Park on November 7-8, 2026 featuring a 5 km Stadion with 20 obstacles, a kids race, and spectator access inside and around the historic ballpark.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A looped 3.1-mile trail course at White Barn Farm in Wrentham MA with distances from 5K to 50K and a central aid station. Runners complete repeatable laps and may stop after any finished loop.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

Trail races in Upton State Forest offer 10.5K and half marathon options over technical, hilly single track and forest roads. The event has a 250 runner cap and aid stations spaced roughly every three miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.

Trail races at YMCA Camp Sloper in Southington CT offering a timed 400 minute loop challenge and a two lap four mile option, chip timing, a main aid station, and proceeds benefitting local organizations.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.