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Fall trail races near Boston (2026)
15 trail races on the calendar from September to November, starting with Womp Romp on Saturday October 24. 6 of them publish an upcoming price increase, so signing up early saves money.
All fall races5K races (90)10K races (4)Half marathons (7)Trail races (15)
By date
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Reg. closed
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from $35Goes up Oct 23
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Powisset Farm Trail Run - Fall
Sun Oct 25 · 8:00 AM · Dover · South Shore
1.5 miles5K5.6 miles8.3 milesTrail
from $20 -
from $10Goes up Oct 24
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from $40
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from $35
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from $10
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from $15
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from $25Goes up Oct 24
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Upton 10.5K and Half Marathon Trail Race
Sun Nov 8 · 9:00 AM · Upton · MetroWest & Worcester
10KHalf marathonTrail
from $30 -
Trailblaze 5 Miler
Sat Nov 14 · 9:30 AM · Westford · North Shore & Merrimack Valley
1K2.5 miles5 milesTrail
from $15 -
Danvers 7 Miler and 4K
Sun Nov 15 · 9:00 AM · Danvers · North Shore & Merrimack Valley
4K7 milesTrail
from $30Goes up Nov 14 -
Gfrc Busa Bushwhack Trail Races
Sun Nov 15 · 9:00 AM · Framingham · MetroWest & Worcester
5.3 miles10 milesTrail
from $35Goes up Nov 14 -
28th Annual Novemberfest Race for the Nashua Children's Home
Sun Nov 22 · 11:33 AM · Nashua · Southern New Hampshire
4 milesTrail
from $25 -
from $25Goes up Nov 25