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Trail Running Calendar near Orland 2026-2027

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Explore the top trail runs near Orland for 2026-2027! We've gathered 6 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
10
Sa

Downeast Trail Festival

Trail Run 6 km 12 km 17 km 52 km
A trail running festival in Sullivan, Maine offering 52K, 17K, 12K, and 6K courses through Baker Hill and Long Ledges while supporting the Frenchman Bay Conservancy.
Oct
17
Sa

Frost Fixed-Time Footrace

Backyard Ultra 5 km
Trail footraces at Caribou Bog Outdoor Center on 17 Oct 2026 feature a 5ish K and a 6 hour fixed time event with blue and red loop options where laps earn points for individuals and teams.
Oct
25
Su

Wildlands Summit Run

Trail Run 6 mi
A trail fundraiser featuring a 6.2 mile summit run to the 1,009 foot peak of Great Pond Mountain and a 1 mile Fun Run to the Dead River.
July 2027
Jul
3
Sa

Move Free Whoopie Mile

Road Race Trail Run
Quarter mile laps where runners eat a whoopie every lap, with solo mile, relay team, and endurance divisions on the College of the Atlantic campus.
August 2027
Aug
7
Sa

Blue Hill Mountain Trail Fest

Trail Run 5 km 10 km 25 km 50 km
Multi-distance trail race on Blue Hill Mountain, Maine, featuring looped 5k, 10k, 25k and 50k courses across wildflower fields, technical forest trails, and coastal viewpoints.
September 2027
Sep
11
Sa

Megunticook Trail Festival

Trail Run 10 km 20 km 50 km
Three trail races in Camden Maine offering a 50K, a 20k on wide trails, and a 10K with ocean views and significant elevation.
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