Trail Running calendar near Brookline 2025-2026

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

Homecoming Chargers 5k Run/Walk is a community event in Blackstone, Massachusetts, scheduled for Saturday, September 27, 2025, at 175 Lincoln Street. The 5k Run/Walk uses Blackstone-Millville Regional's home cross-country course, offering a mix of grass and pavement with a finish on the track. The e..

Ocean State XC Invitational features the Ocean State 5K Trail Run, held at Goddard Park in Warwick, Rhode Island (1095 Ives Road). The 5K course winds through bay-side trails and grasslands, described as a fast, flat off-road route with the start and finish near the clubhouse for the public golf cou..

The Vermont 50 Ultra Run is part of the Vermont 50 endurance weekend held at Ascutney Outdoors in West Windsor, Vermont. It includes a 50‑mile Ultra Run and a 50K Run, plus related relay options and other activities that showcase a challenging yet scenic Vermont landscape. Runners traverse the hills..

The Moosup Valley 5K and 10K All Trail Race takes place in Moosup, Connecticut, on the newly restored Moosup Valley State Park Trail. This event features a 5K, a 10K, and a Kids Fun Run, all held on a 100% trail course that crosses only one dead-end road. The race starts and finishes at the Griswold..

Run for Nature in Lowell, Massachusetts returns to Shedd Park at 453 Rogers Street as a fundraiser hosted by the Lowell Parks and Conservation Trust. The event offers a 5K Run/Walk, a 10K Trail Run (no walk option), and a Kids 1-Mile Fun Run/Walk, a course through park trails and riverfront scenery...

Race for the Refuge takes place at Assabet River National Wildlife Refuge in Sudbury, starting at the Visitor Center. The event includes a 1-mile Walk, a 10K (one loop), a 30K (three loops), plus 3- and 6-hour timed races. The course uses double-track trails with ~2.5 miles of pavement per loop and..

The Bobcat Ridge 25k is a 25k trail race held on the trails of the Edwin L. Smith Preserve in Kennebunkport, Maine. The event takes place on Saturday, October 4, 2025, at the Edwin L. Smith Preserve Trailhead on Guinea Road. All proceeds from the race go directly to the Kennebunkport Conservation T..

The Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

NipMuck Trail Marathon, in Ashford, CT, features two options: the original NipMuck Trail Marathon (26.4 miles) and a two-person NipMuck Relay. The race uses a 13-mile middle segment of the Nipmuck Trail, running south to Route 44, back to the start, then north to Boston Hollow before finishing at Pe..

Trust Trail Fest takes place on October 5, 2025 at the Kennebunkport Conservation Trust headquarters, 57 Gravelly Brook Road, Kennebunkport, ME. Participants can choose a trail 5k or 10k course that winds through the KCT trail system and finishes at the headquarters. The courses are on forest trail..

Groton Town Forest Trail Races, held at 163 West Main Street, Groton, MA, offer two trail distances: 9.5 miles and 3.4 miles. The courses are well-marked and feature a scenic loop through Groton Town Forest with no road crossings, combining narrow dirt roads and single-track trails over roots, rocks..

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds more challenging rolling singletrack and elevation. Runners..

Blackhawk Blaze is a trail running event held in Plainfield, New Hampshire (Meriden area), at 92 Bonner Road, near Plainfield School. This sixth annual Plainfield tradition offers two races: a 5K Trail Race on the famed French's Ledges trail and a 1 Mile Fun Run. The course showcases rugged terrain..

Stairs4RTroops 2025 at Gillette Stadium in Foxboro, Massachusetts is a stair climb, walk, or run up the stadium stairs and around the lower concourses. Held on October 5, 2025, the event features multiple waves roughly every 15 to 30 minutes, including a special Firefighter Wave. The first 2,000 reg..

The Midstate Massive Ultra Trail is a multi-distance, point-to-point trail race organized by New England Race Events in New Ipswich, New Hampshire, with routes extending into nearby Massachusetts and Rhode Island. It offers 100-mile, 50-mile, and 50-kilometer options, tracing the historic Midstate T..

The Wayland / HFC Striders XC Festival, held in Wayland, Massachusetts, is a vibrant cross-country running event featuring three youth 3K races and two open 5K races for adults. The course winds through scenic fields and wooded trails, offering a challenging and enjoyable experience for runners of a..

Vulcan's Fury Trail Race in Nottingham, New Hampshire offers two rugged courses—the Half Marathon and the 5 Miler—set on hiking trails through a once volcanic landscape at Pawtuck. The course is described as technical and scenic, featuring a massive boulder field, dense forest, single-track switchba..

The North Face Race to the Summit is a mountain-top running event held at Stratton Mountain in Stratton, Vermont. The course covers about 2.18 miles with a 2,003-foot vertical climb, delivering a steep uphill challenge amid alpine terrain. The race is timed with live results and leaderboards, with o..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.