Trail Running calendar near Portland 2026-2027

Mile for Mentoring is a one mile community event in Gilford, NH on October 4, 2026, with adult and youth categories and a free entry for children under 12. Early registrants before September 16 receive a complimentary race shirt.

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 rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

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.

A mountain running event in North Conway, NH on October 17, 2026, featuring two race options on Cranmore Mountain and $7500 in cash prizes. The course uses ski slopes, singletrack, and service roads and includes one aid station.

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.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

A mountain race at Cranmore Resort on November 7, 2026, offering 5 km and 10 km courses on access roads and ski trails, marked with reflective flagging and LED lanterns; headlamps are required and registration is online.

A Thanksgiving morning trail event in Jackson NH featuring a 5k on the Jackson nordic trails and a 1k kids fun run for age ten and under, staged at Eagle Mountain House with proceeds supporting local youth programs.

US Snowshoe Nationals 2027 in Concord, New Hampshire features four races over two distances, separate awards including top 3 AGs, a flat course through fields and singletrack, and weekend social events.