Trail Running calendar near Greenwood 2025-2026

Event overview Devil's Den Ultra takes place October 11-12, 2025 in Bradford, Vermont, at 1250 Chase Hollow Rd. The event offers these race options: 30-Hour 12 Hour 6 Miler The event is capped at 100 runners. Registration closes on Octobe..

Take on a unique 100k human powered race across six Maine trail systems, blending 25k of running with 75k of cycling. Expect rugged climbs, scenic overlooks and a feel good finish while supporting local nonprofits.

Sugarloaf Uphill Climb is Maine’s toughest mountain run in Carrabassett Valley. The three-mile course climbs nearly 2,500 feet from the bottom of the SuperQuad to the resort’s 4,237-foot summit—the top of Maine’s second-highest peak—along t..

Enjoy vibrant New Hampshire foliage at the Fall Foliage Foot Races in Waterville Valley on Oct 12, 2025. Choose a flat 5K, a scenic 10 mile trail with a climb and downhill finish, or a 1 mile kids run. Limited spots remain for the 10 mile.

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..

Event overview Big Brad Ultras takes place in Pownal, ME at 528 Hallowell Rd on October 26, 2025. The event offers the following distances: 50 Miler - three laps 50K - two laps 25K - one lap Registration closes October 19, 2025. There is..

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..

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.

CircumBurke on Nov 1 at Victory Hill is an 18 mile singletrack, road and cart trail loop with short steep rocky sections that reward mountain running skills. Proceeds fund trail maintenance and the day offers aid stations, tacos and a beer.

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.

Event overview The Chocorua Mountain Race is a 23K mountain running race in the White Mountain National Forest, starting and finishing from Scott Road in Tamworth, New Hampshire. The course includes about 4,800 feet of cumulative climbing...

Conquer Cannon Mountain in the Cirque Series on June 13, 2026. This rugged 6.9 mile course climbs 3,080 ft to a 4,031 ft summit with steep rocky trails and stunning views, capped at 500 runners with swag and pro photos.

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 climbs Mount Washington via the historic Cog Railway with options to summit or run a 5.5 mile roundtrip. Tackle steep rocky trails, earn a bracelet finisher token and ride the Cog back down.

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.

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..