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Trail Runs Found In Boston, Massachusetts

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Trail Runs in & near Boston, Massachusetts 2025 - 2026

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

Race Calendar: Trail Runs Found In Boston, Massachusetts

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Wheels for the World

Danvers, Massachusetts
01 Jul 25 - 24 Nov 25
Free - $54.00
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2025 Farm to Trail 5K Series @ White Barn Farm

Wrentham, Massachusetts
26 Apr 25 - 25 Oct 25
Free - $32.80
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2025 Farm to Trail 5K Series @ White Barn Farm

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

4K Trail Run

Boston, Massachusetts
24 May 25 - 26 Jun 25
Free - $103.01

4K Trail Run

Boston, Massachusetts
26 Jun 25 - 20 May 26
Free - $103.01

Wheels for the World

Danvers, Massachusetts
01 Jul 25 - 24 Nov 25
Free - $54.00

Watermelon Wobbler 5k @ White Barn Farm

Wrentham, Massachusetts
16 Aug 25
$32.80

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

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

Milton, Massachusetts
05 Oct 25
$32.80 - $38.10

Weir River Farm Trail Race

Hingham, Massachusetts
19 Oct 25
$42.34 - $59.30

Pumpkin Pacer 5k @ White Barn Farm

Wrentham, Massachusetts
25 Oct 25
Free - $32.80

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

Wildcat 5K Trail Run-Walk-Wag

Boxford, Massachusetts
30 May 26
$32.80
Showing 1-13 of 13 results