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Connecticut Trail Running Calendar 2025-2026

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Explore the best trail runs in Connecticut for 2025-2026! Our updated list features 37 exciting races across the region. Find your next race in Connecticut below and join the running community at these great events!

October 2025
Oct
18
Saturday

Tackle the Trail - Pomfret, CT

Trail Run 10 km 21 km 42 km
Oct
18
Saturday

Tom Centinaro Memorial "Dam" Race

Trail Run 4 mi
Oct
19
Sunday

Bimblers Bluff 50k

Trail Run 50 km
Oct
25
Saturday

Cheshire Community YMCA 5K Harvest Trail Run

Trail Run 5 km
November 2025
Nov
2
Sunday

8 Hours At The Farm

Trail Run 4 mi 4 hr 8 hr
Nov
2
Sunday

Stonington Vineyards Wine Run Turkey Trot 5k

Trail Run 5 km
Nov
9
Sunday

Thompson Turkey Trot

Trail Run 3 km 5 km
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km 21 km 42 km
Nov
22
Saturday

Fall Fling

Trail Run 4 mi 400 min
Nov
27
Thursday

Roxbury Thanksgiving Day Charity Race

Trail Run 5 km
December 2025
Dec
6
Saturday

Tower Tag Challenge

Trail Run 3 mi
Dec
13
Saturday

Frosty Forest 5K

Trail Run 5 km
March 2026
Mar
28
Saturday

Northern Nipmuck Trail Race

Trail Run 16 mi
Mar
29
Sunday

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
April 2026
Apr
4
Saturday

Run Across CT

Trail Run 100 km 200 km
Apr
26
Sunday

Jack Bristol Lake Waramaug Ultra Races

Trail Run 50 km 50 mi 100 km
June 2026
Jun
14
Sunday

Nipmuck South Trail Race

Trail Run 16 mi
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