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Trail Running Calendar near Wareham 2026-2027

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Explore the top trail runs near Wareham for 2026-2027! We've gathered 7 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026
Oct
24
Sa

Womp Romp

Trail Run 10 mi 50 km
Trail races in Wompatuck State Park near Hingham MA featuring a 10 Miler and a three-loop 50K with two aid stations and a cupless policy.
Oct
24
Sa

Relentless Run & Ruck Challenge

Trail Run 5 km 10 km
Timed trail event at Camp Greenough with Run or Ruck divisions on a closed 5K loop offering 5K, 10K, and a six-hour lap challenge.
Oct
24
Sa

Sheriff's Meadow Foundation Trail Run

Trail Run 3 mi
A free trail run at Caroline Tuthill Preserve on October 24, 2026 featuring a roughly 3.1 mile loop through pitch pine forest, marsh edges and a raised boardwalk.
Oct
25
Su

The Baystate Dirty Dog Trail Run-Ruck-Walk 5K

Trail Run 5 km
A rugged 5k trail run, ruck, and walk in Berkley MA on October 25, 2026 that honors military and first responder K9 teams while supporting local charities.
Oct
31
Sa

Grumpy's Cranberry Harvest 5K

Trail Run 5 km
A 5K on October 31, 2026 at AD Makepeace in Wareham MA around cranberry bogs, with on-site registration, age-group awards and a connection to the Cranberry Educational Foundation.
November 2026
Nov
14
Sa

DNRT Trail Race

Trail Run 5 km 10 mi
Trail races and a walk through Destruction Brook Woods in Dartmouth with 10 mile and 3.1 mile options, plus post race pizza, beer, and recovery services.
Nov
22
Su

"I'd Rather Be Indoors"

Trail Run 5 km
A 5K off-road run on the Mt Hope HS cross country course in Bristol with start and finish at Bristol Town Beach, with proceeds supporting Mt Hope HS indoor track.
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