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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 30 exciting races across the region. Find your next race in Connecticut below and join the running community at these great events!

November 2025
Nov
16
Sunday

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
22
Saturday

Fall Fling

Trail Run 4 mi 400 min
Nov
23
Sunday

Brooksvale Trails Turkey Trot

Trail Run 5 km 10 km
Nov
23
Sunday

Hartford Track Club 8K Cross-Country Challenge

Trail Run 8 km
Nov
27
Thursday

Roxbury Thanksgiving Day Charity Race

Trail Run 5 km
Nov
27
Thursday

Soul n Body Thanksgiving 5k

Trail Run 5 km
Nov
28
Friday

Darien Depot Overstuffed Turkey Trot 5k

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
Dec
14
Sunday

Taco Trials

Trail Run 10 mi
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
11
Saturday

Hartford Track Club Quarter Marathon

Trail Run 7 mi
Apr
18
Saturday

Traprock 50

Trail Run 17 km 50 km
Apr
25
Saturday

Lake Mohegan Women's Trail Race

Trail Run 5 km 10 km 4 hr
Apr
26
Sunday

Jack Bristol Lake Waramaug Ultra Races

Trail Run 50 km 50 mi 100 km
May 2026
May
3
Sunday

The Blue 2 Blue Challenge

Trail Run 50 km
May
24
Sunday

Mine Hill Half Marathon

Trail Run Half Marathon
June 2026
Jun
4-7
Th - Su

Ironhike Endurance Series - Spring

Trail Run 15 mi 28 mi ... 100 mi 152 mi
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