Trail Running calendar near Bridgewater 2026-2027

A 5K trail run and 1 mile fun run at Tibbetts Field in Madbury NH on October 4, 2026, with a two mile loop through Powder Major Forest and natural trail features including roots, mud, leaves and a hay-bale hurdle.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

A trail event on Wright's Mountain in Bradford, VT, offering 30-hour, 12-hour and 10K options on a mixed-terrain 10K loop, limited to 100 runners and featuring themed tarot-card awards and milestone prizes.

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.

An October trail event at Trapp Family Lodge in Stowe, Vermont featuring a 13.1 mile loop used for both full and half marathon distances. The course mixes wide dirt roads and rugged single track with steep climbs to Round Top Mountain.

A multi format trail event on the Granite Town Rail Trail in Brookline and Milford NH on October 17 and 18 2026, featuring 7.5 mile relays, 15 mile and 30 mile races and a 30 hour ultramarathon. Proceeds support local trail conservation.

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.

A trail event in Windham, ME offering a 50k made of five 6.5 mile loops and a single loop 10k. The course follows Purple, Red, and Blue trails with aid stations and volunteer support.

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.

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A fourth annual community run at Emmons Preserve in Kennebunkport offering timed 5K and 10K races plus a kids 1/2 mile fun run, music, family activities, a wood burned finisher medal and a raffle with local prizes.

Hugs From Vets Trail 10Kish in Henniker, NH on November 1 is a trail and country road race supporting American Legion Post 78. The field is limited to 150 participants and awards recognize overall and age group finishers.

Timed running event offering several durations in New Boston, NH on a 4.0 mile loop along the New Boston Rail Trail. Chip timing, a central aid station, 100 mile buckles for individuals and teams, and specific pacer and camping rules apply.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A night mountain race at Cranmore Resort on November 7, 2026 offering 5k and 10k courses across ski trails and access roads. Headlamps are required and the event includes bib swag, pizza, apres, and awards.

A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A Thanksgiving morning trail 5k in Jackson, New Hampshire, with a 1 km kids fun run for ages 10 and under. Proceeds benefit Jackson Grammar School and Girls on the Run.