Trail Running calendar near Freeport 2025-2026

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. D..

Randolph Ramble is a 5.7-mile trail race on Randolph Mountain Club lands in New Hampshire’s Northern Presidentials. The course climbs about 1,100 feet and is steep, rocky, and slippery, with occasional snow; most runners walk or power-hike..

Located at Lost Valley in Auburn, Maine, the Maine Summit Trek for Tree is a community fundraising event hosted by Lost Valley to benefit Tree Street Youth. The centerpiece is the Endurance Hiking Challenge: participants run, hike, or walk..

Join Quarry Road Trailfest in Waterville on October 26 for costume friendly trail races and a lively afterparty. Pick a 5km or a 15km single track challenge, then celebrate with music, awards and food.

Big Brad Ultras offers rugged single track trails around Bradbury Mountain with 25K, 50K and 50 mile options, limited to 75 runners per race. Expect hilly, technical terrain, well stocked aid stations and a scenic New England challenge.

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..

Run into the night at Cranmore Resort with a fun 5K or 10K mountain race under LED lanterns and reflective flags. Headlamps required, postrace pizza and apres create the perfect evening of trail racing and celebration.

Event overview The Jackson 5k Turkey Trot & Kids Fun Run is a Thanksgiving morning running event in Jackson, New Hampshire. Distances offered include: 5k Turkey Trot 1k Kids Fun Run (10 and under) Awards are given to the top three men..

Riverlands 100 & Relay is a trail ultramarathon held in Turner, Maine, on May 2–3, 2026. The event centers on a 100‑mile race with a relay option, inviting solo runners and teams to tackle the course over two days. The race information page..

Choose 24 hour, 12 hour or 6 hour timed loops at White Lake State Park in Tamworth, NH on May 2, 2026. Enjoy scenic 2 mile loops with some technical trail and beach sections; this is a cupless event so bring your own hydration.

Run the Chocorua Mountain Race, a rugged 14.2 mile course through the White Mountains with steep trails and scenic summit views. Limited to 250 runners, this challenging mountain race rewards experienced trail runners.

Hit the trails in Standish, Maine on June 13, 2026 for the Otter Pond Trail Races, featuring a scenic 10K, a lively Kids Fun Run, and a Dawn to Dusk challenge. Perfect for runners and families seeking a day of outdoor fun.

Race The Cog on June 27 sends runners up alongside the Mount Washington Cog Railway to the summit, with a 2.75 mile Summit Climb or a longer Roundtripper. Expect steep, rocky trails, sweeping alpine views, and a memorable cog train descent.

Join the Back Cove Backyard Ultra in Portland ME for a scenic, mostly flat 4.16 mile loop repeated until one runner remains. Enjoy tidal estuary views, aid at the start and finish, and a friendly volunteer crew.

Baldface Scramble in Evans Notch, NH on July 25, 2026 pits runners on exposed single track with steep ledges and scrambling across the Baldfaces. Choose a bold 29K double loop over Mount Meader or a stout 14K for epic mountain views.

Run rugged White Mountain terrain at Jigger Johnson Ultras in Waterville Valley, NH with 108, 58 and 20 mile options over technical ridgelines and high peaks. Expect remote aid stations and required mountain gear for a bold ultrarunning tes..

Firebird Trail Races : Windham, ME Firebird Trail Races offers trail events in Windham/Falmouth, Maine, with multiple distance options and a technical single-track course. Registration opens on Jan 1, 2026. Entry requires a registration fee..

Test your limits at the Last Man Standing Ultramarathon on September 5, 2026 at Pineland Farms in New Gloucester, Maine. Run repeating 4.2 mile wooded loops until a single finisher remains in this backyard ultra classic.

Experience coastal singletrack and mountaintop views at the Megunticook Trail Festival in Camden Hills State Park, Midcoast Maine. Choose 10K, 20K or a sprawling 50K and enjoy an inclusive event with Indigenous runners welcome to enter free..