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Fall trail races near Boston (2026)
Updated
15 trail races are on the calendar near Boston in fall 2026, starting with Womp Romp on Saturday, October 24 in Norwell. That covers September to November. 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
Other seasons near Boston
Quick answers
How many trail races are near Boston in fall 2026?
15 trail races are listed near Boston in fall 2026. The first is Womp Romp on Saturday, October 24 in Norwell, and the last is Turkeywacker 5K on November 26.
What is the cheapest trail race near Boston in fall 2026?
Clocker Club 5k Fundraiser on October 25 has the lowest listed entry fee: $10. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Boston?
Pumpkin Pacer 5k @ White Barn Farm: the 5K goes from $35 to $50 after October 23. 5 more of these trail races publish a later price increase.
Are there half marathons or marathons near Boston in fall 2026?
Yes: 1 half marathon and 0 marathons. The first is Upton 10.5K and Half Marathon Trail Race on November 8.