Trail Running calendar near Westwood 2025-2026

We have found 45 Trailruns within 80 miles of Westwood. See below where and when you can find the races.

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

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..

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.

December 2025

Take on the TARC Winter Classic at Middlesex Fells with 8, 32 and 40 mile Skyline Trail loops featuring roots, climbs and occasional Boston skyline views. Limited spots, cupless aid and winter trail conditions make this a true test for expe..

Tackle the Mount Hood Nutcracker Challenge through much of the Mount Hood Golf Club with a scenic 3.5 mile cross country race or a 2 mile walk. Limited field, team and individual entries, nutcracker awards, pasta lunch and charity support.

Run Seth's Fat Ass 50K on Saturday December 20 2025 at Forest Park in Springfield MA, a friendly looped ultra offering one to ten 5K laps with a seven hour cutoff. Relaxed vibe, easy parking and race day registration welcome runners of all..

February 2026

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.

March 2026

Join Ramsey's Run, a scenic 5k trail run through the woods in Kingston MA on Saturday March 14, 2026. This memorial event honors a Class of 2023 student and raises funds for a scholarship established by the family.

Lace up for a scenic 3.5 mile wooded loop at Hale Education in Westwood, with a timed 6 hour challenge or a shorter lap option. Expect roots, boardwalks and ponds; proceeds support land conservation and the event is cupless so bring your ow..

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.

April 2026

Run the Tortoise and the Hare Trail Races on April 4, 2026 at Lions Park in Salisbury with 10K, 5K and a fun 1 mile color run. Family friendly trails, music and post race treats with proceeds supporting Salisbury Parks and Recreation.

Run Across CT 123 is a scenic 123 mile ultramarathon across Connecticut from East Thompson to Southport, weaving through forest trails and backroads. Enter as a timed solo or relay team and challenge yourself to finish within the 36 hour cu..

The Merrimack River Trail Race is a USATF-sanctioned 10-mile out-and-back trail run held in Andover, Massachusetts, starting from the DoubleTree by Hilton Hotel parking lot. The course features water stations at miles 2, 4, and 8, with a mi..

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..

Run the scenic trails of Jericho Town Forest in Weston, MA with distances from 10K to 50K on a fast, smooth loop. Welcoming to youth, adaptive athletes, and volunteers; note the event is cupless so bring your own hydration.

May 2026

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

TARC Wapack and Back is a rugged ridge trail race on the Wapack Trail with 21.5, 43 and 50 mile options over rocky, technical terrain and big climbs. Expect minimal markings and serious elevation so seasoned trail runners only.

Experience the 9th annual Wildcat 5K Trail Run, Walk and Wag on May 30, 2026 in Boxford, a scenic 5K around Stiles Pond through Wildcat State Forest. Runners, walkers and their dogs will enjoy trails, prizes and a festive post race celebrat..

June 2026

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Enjoy the Nipmuck South Trail Race in Mansfield CT, a 15.7 mile out and back along the Fenton River that winds through woods, fields and over small bridges. Organized by Shenipsit Striders, proceeds benefit local trail stewardship.