Trail Running Calendar near Drakes Island Beach 2026-2027

October 2026

Sanford | 13 mi from Drakes Island Beach

Road Race Trail Run 5 km

A community 5K run and walk in Springvale supporting a nonprofit that provides technology to seriously ill children, with awards, kids activities, and a post race barbecue.

Oct

31

Sa

Holistic Hustle

Kennebunkport | 4 mi from Drakes Island Beach

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

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

Mingle Jingle Run

Sanford | 13 mi from Drakes Island Beach

Road Race Trail Run 5 km

Holiday-themed event in Sanford ME featuring an in-person 5K, a kids Turkey Trot on the stadium track, and a virtual 5K plus a costume contest and raffle.

Nov

21

Sa

Powderhouse Hill Climb Challenge

South Berwick | 14 mi from Drakes Island Beach

Trail Run Backyard Ultra

Four hour community hill challenge at Powderhouse Hill in South Berwick, Maine; open format climbs, $35 entry includes long sleeve shirt and post challenge lunch.

May 2027

May

8

Sa

Rescue Run: Race for Marine Mammals

Rye | 25 mi from Drakes Island Beach

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.

July 2027

Jul

10

Sa

Back Cove Backyard Ultra

Portland | 27 mi from Drakes Island Beach

Backyard Ultra 4 mi

Back Cove Backyard Ultra in Portland, ME on July 10, 2027 has runners complete a roughly 4.16 mile loop each hour until only one runner remains, with staffed aid and free parking.