Vermont Trail Running Calendar 2025-2026

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Explore the best trail runs in Vermont for 2025-2026! Our updated list features 67 exciting races across the region. Find your next race in Vermont below and join the running community at these great events!

September 2025
Sep
6
Saturday

Groton Forest Trail Run

Trail Run 10 km 25 km 26 mi
Sep
6
Saturday

Saucony Charlotte Covered Bridge Half Marathon

5 km 10 km 13 mi
Sep
13-14
Sa - Su

Vermont Spartan Event Weekend

Obstacle Run 5 km 21 km 50 km
Sep
13
Saturday

Brain Freezer 5K

5 km
Sep
14
Sunday

Island Vines 10k

5 km 10 km
Sep
20
Saturday

Apple Harvest 10k

10 km
Sep
20
Saturday

Miles for Migraine Vermont

2 mi 5 km
Sep
21
Sunday

Trapp Cabin Trail Races

5 km 10 km 13 mi
Sep
21
Sunday

Tam Trek

Trail Run 2 mi 10 km 19 mi
Sep
27
Saturday

Westmore Mountain Challenge

Trail Run 26 mi
Sep
28
Sunday

Vermont 50 Ultra Run

Trail Run 50 mi
October 2025
Oct
5
Sunday

Leaf Peepers Half Marathon

5 km 13 mi
Oct
11-12
Sa - Su

Devil's Den Ultra

Trail Run 6 mi 12 hr 30 hr
Oct
18
Saturday

Trapp Lodge Mountain Marathon

Trail Run 13 mi 26 mi
Oct
19
Sunday

Champlain Islands Marathon

13 mi 26 mi
Oct
19
Sunday

Champlain Islands Marathon and Half Marathon

13 mi 26 mi
Oct
19
Sunday

Middlebury Maple Run

5 km 10 km 13 mi
Oct
25
Saturday

Union Bank Field House Half Marathon

5 km 10 km 13 mi
Oct
26
Sunday

Hills Are Alive Cross Country Race

Trail Run 5 km
November 2025
Nov
1-2
Sa - Su

RutFest

Trail Run 4 mi
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