Trail Running calendar near Freeport 2025-2026

The Moxie's Memorial will take place in Oxford on Sunday 28 September 2025. You can run 5 kilometers.

The Bobcat Ridge 25k will take place in Kennebunkport on Saturday 4 October 2025. You can run 25 kilometers.

Bubba's Backyard Ultra, held in Center Conway, New Hampshire, is a unique endurance running event featuring the Last Person Standing format. Participants run a 3.5-mile loop primarily on forest singletrack, with some snowmobile trails, fields, and logging roads, including about 250 feet of elevation..

The Little Duck 50k is a trail running event held in Windham, Maine, at the scenic East Windham Conservation Area. Scheduled for October 5, 2025, it offers two race distances: a challenging 50k ultra-marathon consisting of five 6.5-mile loops with nearly 1,000 feet of elevation gain per loop, and a..

Trust Trail Fest, held at the Kennebunkport Conservation Trust headquarters in Kennebunkport, Maine, offers participants a choice between a 5k walk/run and a 10k run through scenic forest trails. The courses feature natural terrain with rocks, roots, and possible mud, providing a challenging and imm..

The Vulcan's Fury Trail Race, held in Nottingham, New Hampshire, offers a challenging and scenic trail running experience inspired by the area's volcanic history. Participants can choose between a half marathon and a 5-mile race, both featuring rugged terrain including massive boulder fields, dense..

The Land of Light 100k is a unique human-powered race held in Norway, Maine, featuring a combination of running and cycling across six distinct trail systems. The event covers a total of 100 kilometers, with 25k of running and 75k of cycling, starting at Virgil Parris Preserve. Participants navigate..

The Randolph Ramble is a challenging 10-kilometer trail race held in the mountain town of Randolph, New Hampshire, nestled in the Great North Woods at the base of the Northern Presidentials. Known for its rugged terrain, the race emphasizes self-sufficiency, with no aid stations along the course and..

The Thorne Head Trail Run is a community-focused 4k trail race held at Thorne Head Preserve in Bath, Maine. Hosted by the Kennebec Estuary Land Trust, this event features a mix of fun single-track and wider trails with scenic water views. Designed to be inclusive for both first-time trail runners an..

The Big Brad Ultras, held in Pownal, Maine, offers challenging trail races featuring a 16.5-mile loop through Bradbury Mountain State Park, including Tryon Mountain and Snowman's loop. The course is rugged with hills, rocks, roots, and minimal flat terrain, plus a short stretch of paved and dirt roa..

The Blackout 5k/10k is an exciting mountain race held at Cranmore Resort in North Conway, New Hampshire. This nighttime event features 5K and 10K distances run on a course combining access roads and ski trails, marked with reflective flagging and LED lanterns to guide participants. Headlamps are man..

The Holistic Hustle 5K/10K is an annual running event held at the scenic Emmons Preserve in Kennebunkport, Maine. The 4th edition, scheduled for November 1, 2025, features timed 5K and 10K run/walk races alongside a kids' half-mile fun run for participants aged 13 and under. The event offers a livel..

The Jackson 5k Turkey Trot & Kids Fun Run is a Thanksgiving morning event held in Jackson, New Hampshire. It features a 5k trail run through scenic routes including the Jackson Nordic Trails and Eagle Mountain House golf course, starting at Jackson Falls Bridge. There is also a 1k Kids Fun Run for c..

The Back Cove Backyard Ultra is a unique endurance running event held in Portland, Maine, on the scenic Back Cove Trail. Participants run a 4.167-mile loop every hour on the hour, continuing until only one runner remains. The course features a mostly flat, non-technical 3.5-mile gravel loop along a..