Trail Running calendar near Jackson 2026-2027

A multisport festival at Pawtuckaway State Park offering swim, bike and run options for people who identify as women. Choose an individual triathlon, two sport combo, single sport or a relay team in a non competitive setting.

Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.

Trail-based looped ultra at Wolfe's Neck Farm in Freeport featuring a new all-trail five mile loop repeated for ten, six, or two laps depending on distance.

Bike, run, or walk on the Lamoille Valley Rail Trail in Morrisville, Vermont. Proceeds support services for healthy aging in Central Vermont including groceries, emergency fuel, prescription assistance, and exercise classes.

A 21k trail race on Pleasant Mountain in Bridgton, ME, featuring steep ridge climbs, technical single-track, one aid station, and a finish-area afterparty with food and beer.

Trail races on Paine Mountain near Northfield VT featuring a 7 mile plus summit race, a 6k Anchor Challenge with a 4 person team option, youth races and awards.

Last person standing trail ultra in Center Conway, NH on a 3.5 mile forest loop with camping, meals, swag and a beer mile the following day.

A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, ME on October 3, 2026, with proceeds benefiting the Kennebunkport Conservation Trust and registration capped at 100.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

Trail 5k in Oxford, Maine starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs; properly trained service dogs only and beer tickets for those 21 or older.

Trail event in Bradford Vermont with looped mountain course, 30 hour, 12 hour and 6 mile options, tarot themed awards and a 100 runner cap.

A community run on October 10, 2026, organized by the Lebanon Recreation, Arts, and Parks Department, following the Rail Trail from Enfield along Mascoma Lake and the Mascoma River to a finish in Lebanon. Fees change before race week and pa..

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 fully human powered 100K in Norway, Maine mixing 25k of trail running and 75k of cycling across six preserves, offered as solo and duo with charitable beneficiaries.

A coastal 5K at Hermit Island Campground supporting Marine Mammals of Maine, with timed and untimed in-person runs, a weeklong virtual 5K, a kids 1-mile fun run, raffle, and prizes for top human and canine finishers.

Trail marathon and half marathon at Trapp Family Lodge in Stowe, VT on October 17, 2026, run on a 13.1 mile loop with steep climbs and single track.

Mountain up-and-down race at Cranmore Mountain in North Conway offering 10 km and 5 km options, USATF sanctioned and $7,500 in prize money for 2026.

Trail running event in Windham, ME offering a 50k of five 6.5 mile loops and a single-loop 10k with aid stations and volunteer support.

An uphill run at Stowe Mountain Resort hosted by the Mansfield Nordic Pro Team on June 21 and October 18, 2026. The 1.7 miles course climbs from Midway Lodge to Cliff House and raises funds for the pro team.