Trail Running calendar near Westwood 2025-2026

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

Join the Tortoise and the Hare Trail Races in Salisbury on April 4, 2026 for trail 10K, 5K and a fun 1 Mile Color Run. Enjoy custom tech shirts, post race music and snacks while supporting Salisbury Parks and Recreation.

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..

Spring Fever brings scenic early spring trail racing to Wompatuck State Park in Hingham on April 11, with 5K, 5 mile, and an 8 hour multi lap challenge. Expect muddy trails, on course aid, and a friendly campground finish line vibe.

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.

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 scenic, rugged trail race in May on the Wapack Trail between Massachusetts and New Hampshire, offering 21.5, 43 and 50 mile options. Expect technical terrain, big climbs, limited aid, and a tight knit trail communi..

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

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..

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.

Take on a scenic 15.7 mile trail run on the Nipmuck Trail in Mansfield CT, following the Fenton River through woods, fields and small bridge crossings. Organized by the Shenipsit Striders, proceeds support local trail stewardship.

Join the Stonington Cross Country 5K in Pawcatuck CT on Wednesday August 12 2026 for a free community race that blends one track loop, quiet campus roads and scenic trails. A children's 1/2 mile for ages 10 and under also finishes on the sc..

Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

Tackle a scenic 5K through Oswegatchie Hills Nature Preserve, winding past Clark Pond on root and rock strewn trails; hikers welcome. This fourth annual run benefits preserve maintenance and finishes with local pub awards and camaraderie.

Enjoy scenic 1 Mile and 5K trail runs and hikes at the Annual Trail Challenge on Mount Agamenticus in York, Maine Saturday September 19. Proceeds support conservation and education and a community raffle makes the day festive.

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

Run the Midstate Massive Ultra Trail on October 10 to 11, 2026 across central New England, a UTMB Index point to point ultramarathon along the Midstate Trail. Choose 100 mile, 50 mile or 50K courses that wind through mountains, fields and r..