Trail Running calendar near Westport 2025-2026

Make Thanksgiving morning active at the Turkeywacker 5K in Wrentham, a festive trail run at Rice Recreation Complex with donuts, cider and raffle prizes. Awards for top finishers across ages ensure competition and family fun.

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.

Join Trail Animals Running Club Winter Classic at Middlesex Fells for scenic but rugged Skyline Trail loops with 8, 32, and 40 mile options. Expect rocky climbs, limited aid, cupless racing, and a friendly sold out vibe.

Take on the scenic Mount Hood golf course in Melrose with a 3.5 mile cross country race or 2 mile walk, limited to 250 entrants. Enjoy varied terrain, nutcracker awards and post race pasta while supporting local schools and Housing Families..

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

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.

Run the scenic single track loop at Hale Reservation in Westwood, MA with 3.5 mile or 6 hour options. Trails, pond views and wood bridges await while proceeds support land conservation.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

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.

The Merrimack River Trail Race will take place in Andover on Saturday 11 April 2026. You can run 10 miles.

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.

TARC Spring Classic in Weston MA on April 25, 2026 offers 10K, half, marathon and 50K trail races plus a free youth fun run on a smooth scenic 10K loop. This cupless, multi lap event fills fast so register early as parking and aid are limit..

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 3 mile trail through farmland and finish among the vineyard vines at Westport Rivers Winery, then enjoy wine, BBQ, live music and a souvenir glass. Race entry is 21 and over while BBQ options welcome families.

Run the rugged Flat Rock Trail Race in Dunstable MA on June 13, 2026. Choose a single 5 mile loop or take on a 6 hour loop challenge across rocky climbs, old railroad bed and an arched bridge while supporting the Humane Society for Greater..

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.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

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.