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Massachusetts Trail Running Calendar 2026-2027

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Explore the best trail runs in Massachusetts for 2026-2027! Our updated list features 54 exciting races across the region. Find your next race in Massachusetts below and join the running community at these great events!

August 2026
Aug
22
Sa

Jug End Loop Ultra

Trail Run 4 mi
Aug
22
Sa

Greenbelt's Vineyard Hill Trail Run

Trail Run 5 km 10 km
Aug
23
Su

Old Goat Track Club XC Classic

Trail Run 5 km
Aug
29
Sa

All of the Above Trail Fest

Trail Run 5 km 20 km
Aug
30
Su

UltraTrax Wachusett

Trail Run 7 mi 14 mi 21 mi 28 mi
Monthly updates for Massachusetts

Get new running races (and updates) in your inbox every month.
September 2026
Sep
5
Sa

TARC Fall Classic

Trail Run 10 km Half Marathon ... 50 km 50 mi
Sep
5
Sa

Foot It for Felix 5K

Trail Run 5 km
Sep
5
Sa

Run the Dam for Davenport

Road Race Trail Run 5 km
Sep
5
Sa

Trailblaze 5 Miler

Trail Run 3 mi 5 mi
Sep
13
Su

GBTC XC Invite

Trail Run 5 km
Sep
19
Sa

Codfish Bowl

Trail Run 5 km 8 km
Sep
20
Su

Arc'teryx Run Boston

Trail Run 10 km
Sep
27
Su

Race for the Refuge

Trail Run Backyard Ultra 10 km 30 km 6 hr
Sep
27
Su

Run for Nature - Lowell

Trail Run 5 km 10 km
October 2026
Oct
3
Sa

BLS Wolfpack 5K Cross Country Run or Walk

Trail Run 5 km
Oct
3
Sa

Shrewsbury Trails 5K

Trail Run 5 km
Oct
4
Su

Groton Town Forest Trail Races

Trail Run 3 mi 10 mi
Oct
4
Su

Run Stanley

Trail Run 5 km
Oct
4
Su

Nick's 5K Run & Fitness Walk

Trail Run 5 km
Oct
4
Su

Houghton's Pond Trail Race

Trail Run 4 mi 7 mi
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