Trail Running Calendar near Wiscasset 2026-2027

September 2026

Trail Run 10 mi 30 mi 50 mi

Experience an all trail ultra marathon through the woods and coastal farmlands of Freeport Maine featuring 50 mile 30 mile and 10 mile distances on a scenic 5 mile loop.

Sep

27

Su

Phil Soule Phlail 5K Run & Walk

Brunswick | 16 mi from Wiscasset

Trail Run 5 km

A 5K held at Bowdoin College on September 27 2026 featuring a two-lap grass and dirt trail course around the Pickard Field complex with a $20 entry fee.

October 2026

Oct

10

Sa

Maguire's Midcoast Community Challenge

Wiscasset

Obstacle Run 3 mi

A 3.1 mile obstacle and fitness course in Wiscasset with at least ten moderate obstacles over uneven terrain, water and mud; pre registration available, fee $45.

Oct

11-17

Su - Sa

Ocean Commotion 5K

Phippsburg | 15 mi from Wiscasset

Trail Run 3 mi

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.

Oct

25

Su

Maine Summit Trek for Tree

Auburn | 28 mi from Wiscasset

Trail Run

Community fundraising hike at Lost Valley where participants repeat climbs over a four hour challenge to raise funds for Tree Street Youth.

Oct

31

Sa

Thorne Head Trail Run

Bath | 10 mi from Wiscasset

Trail Run 4 km 3 mi

A short 2.5 mile community trail run at Thorne Head Preserve in Bath with river views, limited to 150 runners; proceeds support the Kennebec Estuary Land Trust.