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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 5 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
Trail races in Sullivan, Maine on October 10, 2026 across Baker Hill and Long Ledges with distances 52K, 17K, 12K and 6K; cupless race and limited on-course support.
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
Trail races in Orland, Maine with a 6.2 mile summit route over forested single track and granite slabs, plus a 1 mile fun run to the Dead River. The event supports the Great Pond Mountain Conservation Trust.
July 2027
Jul
3
Sa

Move Free Whoopie Mile

Road Race Trail Run
A Bar Harbor event where competitors eat a whoopie pie every 0.25 mile lap, with solo, relay and endurance divisions.
August 2027
Aug
7
Sa

Blue Hill Mountain Trail Fest

Trail Run 5 km 10 km 25 km 50 km
A multi-distance trail event on Blue Hill Mountain (Blue Hill, ME) with 5k, 10k, 25k and 50k options, aid stations, and proceeds supporting local conservation and Wabanaki organizations.
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