Trail Running calendar near Upton 2026-2027

Snow or no snow, join the NHTI Lynx on January 10 in Concord for a spirited snowshoe race on scenic college cross country trails with 2 mile, 4 mile and kids events. Proceeds support NHTI Athletics and awards go to top finishers.

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

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 the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Join Ramsey's Run in Kingston MA on March 14, 2026 for a scenic 5k trail run through the woods, timed by a professional company. Honor a class of 2023 member and support a family scholarship with every entry.

Run scenic singletrack loops around ponds and woodlands at Hale Education in Westwood, with a 6 hour endurance option or a 3.5 mile loop. Bring your own bottle for this cupless event and enjoy a laid back aid station at the start.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

Join CT123 on April 4, 2026, a point to point 123 mile ultramarathon across Connecticut that blends trails and backroads for a challenging spring adventure. Solo and relay entries welcome and 200K finishers earn a commemorative belt buckle.

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.

Join the Merrimack River 10 miles on April 11 for a USATF sanctioned out and back trail race starting behind the DoubleTree in Andover. Enjoy water stops, post race bagels and a raffle while supporting local trail maintenance.

Explore wooded trails at Wompatuck State Park in Hingham with 5K, 5 mile and 8 Hour options on April 11. Expect mud, climbs, aid stations and community snacks plus custom finisher awards and bonus swag for early registrants.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Run the Traprock 50 at Penwood State Park in Bloomfield CT on Apr 18, 2026, choosing 50K or 17K looped courses over technical single track and rocky terrain. Chip timing, cupless aid, and proceeds support local conservation.

Enjoy smooth loop trails in Jericho Town Forest with distances from 10K to 50K and a free youth run. This cupless race often sells out so register early and bring your own hydration for vegan friendly aid.

Tackle the rugged Seven Sisters Trail Race on May 2, 2026 along the Holyoke Range ridgecrest in Amherst, MA. This 12 mile out and back packs over 3,500 ft of climbing on technical singletrack with steep, rocky ledges for a true trail challe..

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

Run the Mount Archer Trail Race Sunday May 3 2026 in Lyme CT with a scenic 9.2 mile loop or a 3 mile option for runners and walkers. Chip timing, aid stations, and proceeds support Lyme emergency services.

Hit the trails at the Cape Cod Trail Race on May 3, 2026, with 10K, 20K and 30K options through the scenic Frances A. Crane Wildlife Management Area. Register soon for a community focused day of challenging trails and postrace camaraderie.

TARC Wapack and Back in Ashburnham MA features 21.5, 43 and 50 mile out and back runs on the classic Wapack Trail. Rugged rocky singletrack, big climbs and sweeping views, plus aid stations and headlamp requirements for longer distances.

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.