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Trail Running Calendar near Boston 2026-2027

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Explore the top trail runs near Boston for 2026-2027! We've gathered 24 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

May 2027
May
29
Sa

Outlast Pittsburgh

Trail Run Backyard Ultra
Outlast Pittsburgh is a six hour trail challenge where participants must complete a 5K loop every hour on the hour to stay in the race and earn a finisher medal.
June 2027
Jun
6
Su

South Ridge Trail Challenge

Trail Run 4 mi 7 mi 12 mi 33 mi
Trail races on North Park's South Ridge offering 5K, 10K, 20K, 50K and a 50K relay across summer trails and varied terrain.
July 2027
Jul
11
Su

Murrysville Monster Trail Races

Trail Run 6 mi 12 mi
Trail races in Murrysville, PA on July 11 2027 through Duff Park and Pleasant Valley Park with single track, water crossings and technical obstacles.
August 2027
Aug
1
Su

Two Face 10K

Trail Run 6 mi 7 mi 13 mi
A multi-option running event in North Park, PA offering road, trail, and a combined road-and-trail challenge around the lake and on the Rachel Carson Trail.
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