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Trail Runs found in Massachusetts

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Trail Runs in Massachusetts 2025 - 2026

The most comprehensive list of Trail Runs in and near Massachusetts in 2025 - 2026. Find your perfect race!

Race Calendar: Trail Runs found in Massachusetts

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Dash For Dane & Family Day

Dover, Massachusetts
17 May 25
Free - $38.10
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Powisset Farm Trail Run - Spring

Dover, Massachusetts
26 May 25
$22.20 - $48.70
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Tortoise and the Hare Trail Races

Salisbury, Massachusetts
19 Apr 25
$27.50 - $32.80

Tough Ruck Boston 26.2 For The Fallen

Concord, Massachusetts
20 Apr 25
$160.00 - $2,601.00

2025 Farm to Trail 5K Series @ White Barn Farm

Wrentham, Massachusetts
26 Apr 25 - 25 Oct 25
Free - $32.80

Seven Sisters Trail Race Charity Bibs

Amherst, Massachusetts
03 May 25
Free

7th Annual Cinco de Mayo 5K

Wareham, Plymouth
04 May 25
$30.00

Watuppa Trail Races

Fall River, Massachusetts
10 May 25
$27.50 - $48.70

Dash For Dane & Family Day

Dover, Massachusetts
17 May 25
Free - $38.10

4K Trail Run

Boston, Massachusetts
21 May 25 - 22 May 25
Free - $103.01

Powisset Farm Trail Run - Spring

Dover, Massachusetts
26 May 25
$22.20 - $48.70

Wildcat 5K Trail Run-Walk-Wag

Boxford, Massachusetts
31 May 25
$32.80

Friends of Holliston Trails 5K & 10K

Holliston, Massachusetts
31 May 25
$7.00 - $34.30

Greenbelt's Vineyard Hill Trail Run

South Hamilton, Massachusetts
23 Aug 25
$32.80 - $38.10

Run for Nature

Lowell, Middlesex
28 Sep 25
$6.95 - $40.00

Weir River Farm Trail Race

Hingham, Massachusetts
19 Oct 25
$38.10 - $52.94

Powisset Farm Trail Run - Fall

Dover, Massachusetts
26 Oct 25
$22.20 - $48.70

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

Berkley, Massachusetts
16 Nov 25
$16.90 - $27.50

10th Annual F.O.R 5k Trail Race

Wilbraham, Massachusetts
13 Apr 25
Free

Wheels for the World

Danvers, Massachusetts
01 Jul 25 - 03 Nov 25
Free - $54.00

Houghton's Pond Trail Races (7 Miles and 3.7 Miles)

Milton, Massachusetts
05 Oct 25
$27.50 - $32.80
Showing 1-19 of 19 results