Trail Running Calendar near Rye 2026-2027

October 2026

Trail Run 5 km 10 km

A community run at Emmons Preserve in Kennebunkport featuring 5K, 10K trail and a kids fun run with medals, music, family activities and a raffle.

Oct

31

Sa

Trick or Trail 5K - Wells

Drakes Island Beach | 25 mi from Rye

Trail Run 5 km

A costumed 5K trail run at the Wells Reserve at Laudholm on October 31, 2026 supporting coastal research, with timed results, water stations, awards, and a limited shirt.

November 2026

Nov

7

Sa

TARC Stone Cat Trail Festival

Ipswich | 22 mi from Rye

Trail Run 10 km Half Marathon ... 50 mi 100 km

November trail event at Willowdale State Forest offering looped distances from a free youth fun run to a 100K with fundraising for local land trusts.

Nov

21

Sa

Powderhouse Hill Climb Challenge

South Berwick | 16 mi from Rye

Trail Run Backyard Ultra

A four hour hill climb and community fundraiser at Powderhouse Hill in South Berwick supporting the Marshwood High School Ski Team with BBQ, music, and raffles.

Nov

26

Th

Newburyport Maudslay Turkey Trot 5k

Newburyport | 14 mi from Rye

Road Race Trail Run 5 km

Thanksgiving Day 5K cross-country run/walk at Maudslay State Park supporting local charities, organized by Joppa Flats and Winners Circle Running clubs.

March 2027

Mar

27

Sa

Tortoise and the Hare Trail Race

Salisbury | 11 mi from Rye

Trail Run 3 mi 6 mi

Trail races and a 1 mile Color Run in Salisbury on March 27, 2027, featuring 10K, 5K and a non timed color run, with proceeds supporting Salisbury Parks and Recreation.

May 2027

May

8

Sa

Rescue Run: Race for Marine Mammals

Rye

Trail Run 5 km 300 mi

A chip timed 5K trail race with kids fun runs at Odiorne Point State Park to raise funds for Marine Mammal Rescue, followed by a community beach cleanup.