Trail Running calendar near Freeport 2026-2027

An annual community trail event at Mount Agamenticus offering timed **1 Mile** and **5K** courses from the summit, with proceeds supporting conservation and education and a raffle for participants.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A traditional up and down mountain race in Waterville Valley, NH on September 20, 2026 covering about 7 miles with 3000 feet of ascent; youth entry is available and day of registration is offered.

A community trail festival in Arundel, Maine offering 5k, 10k and half marathon distances on the ACT and Eastern Trail, with participant shirts and medals, a free kids' bike race, live music, and food.

A multisport festival for people who identify as women at Pawtuckaway State Park on September 26, 2026, offering triathlon, two sport, single sport and relay options on supported swim, trail bike and trail run courses.

A looped trail ultra at Wolfe's Neck Farm in Freeport, ME, on a just over 5 mile dirt loop with stairs, bridges, and about 570 feet of gain per loop. Distances include 50 mile, 30 mile, and 10 mile options.

A 21k trail race on Pleasant Mountain in Bridgton, Maine on September 27, 2026. The route includes steep climbs, technical single track, one aid station, and a postrace gathering with food, beer for 21 plus, and live music.

An eighth edition backyard ultra in Center Conway, NH on October 3rd, 2026. Runners loop a mostly forest singletrack course of about 3.5 miles with hourly laps until one person remains, with camping and meals on site.

A 25 kilometer trail race at the Edwin L. Smith Preserve in Kennebunkport on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust. Registration is capped at 100 and a shirt-included cutoff is on September 5.

A one-mile charity run at Gunstock Mountain Resort on October 4, 2026, benefiting Big Brothers Big Sisters of New Hampshire & Vermont. Online registration closes October 2; adult and teen entries are $20, children under 12 enter free.

A 5K trail race and 1-mile fun run at Tibbetts Field in Madbury, NH on October 4, 2026, featuring a 2-mile loop through Powder Major Forest over natural terrain. A portion of proceeds will support a local family in need.

The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.

A technical, rugged trail race at Pawtuckaway State Park offering a half marathon and a five mile course. New for 2026 the event features $7,500 in prize money and multiple aid stations on rocky, forested terrain.

A mixed human powered 100k in Norway, Maine combining 25 km of trail running with 75 km of biking across six preserves. Solo and duo options are available and proceeds benefit TruStrength Tomorrow and Western Foothill Land Trust.

Cranmore Mountain Race in North Conway, NH offers one and two lap up and down mountain courses on ski slopes, singletrack, and service roads, with the two lap race part of the USATF New England circuit and $7500 in cash prizes.

Trail races at East Windham Conservation Area in Windham, ME. The 50k is five 6.5 mile loops and the 10k is one loop, each loop with roughly 900 ft elevation and two aid stations offering snacks, water and electrolytes.

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

Nighttime mountain races at Cranmore Resort on November 7, 2026 featuring 5 km and 10 km courses, reflective markers, required headlamps, and post-event pizza and awards.