Trail Runs in Maine 2026 | Upcoming Races & Dates

There are 5 trail runs in Maine scheduled for 2026. The next is the Trail Festival at Pineland Farms in New Gloucester on May 23. Maine trail runs run primarily May through October.

Trail Festival at Pineland Farms

Sat, May 23 · New Gloucester, ME New Gloucester

Canicross 5k - CompetitiveSunset 5k5k +10

From $34 Open

Cherry Hill Farm Ultra

Sat, Sep 5 · Gorham, ME Gorham

10k Trail Race25k Trail Race50k Trail Race

From $85 Open

Last Man Standing Ultramarathon

Sat, Sep 5 · New Gloucester, ME New Gloucester

Last Man Standing UltramarathonLast Man Standing Ultramarathon Early Access

From $135 Open 59 spots left

Mt. A Trail Challenge 5K/1 Mile

Sat, Sep 19 · York, ME York

Annual Mt. A Trail Challenge - 1 MileAnnual Mt. A Trail Challenge - 5K

From $20 Open 50 spots left

Holistic Hustle 5K/10K

Sat, Oct 31 · Kennebunkport, ME Kennebunkport

Student (13 and under) Timed 5k or 1/2 mile Fun Run5K10K

From $10 Open

Trail Runs in Maine — 2026

Trail Festival at Pineland Farms

Cherry Hill Farm Ultra

Last Man Standing Ultramarathon

Mt. A Trail Challenge 5K/1 Mile

Holistic Hustle 5K/10K

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