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Connecticut Trail Running Calendar 2026-2027

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Monthly updates for Connecticut

Get new running races (and updates) in your inbox every month.

Explore the best trail runs in Connecticut for 2026-2027! Our updated list features 54 exciting races across the region. Find your next race in Connecticut below and join the running community at these great events!

November 2026
Nov
1
Su

8 Hours At The Farm

Trail Run 5 km 4 mi
Nov
8
Su

Stonington Vineyards Wine Run Turkey Trot 5k

Trail Run 5 km
Nov
15
Su

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
21
Sa

Storybook Half Marathon

Trail Run 13 mi
Nov
21
Sa

Fall Fling

Trail Run 4 mi 400 min
Nov
26
Th

Soul N Body Thanksgiving Trail Run

Trail Run 4 mi
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run 3 mi
Dec
19
Sa

Frosty Forest 5K

Trail Run 5 km
March 2027
Mar
28
Su

Northern Nipmuck Trail Race

Trail Run 16 mi
April 2027
Apr
3
Sa

Run Across CT

Trail Run 100 km 200 km
Apr
4
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
Apr
17
Sa

Traprock 50

Trail Run 17 km 50 km
Apr
24
Sa

Lake Mohegan Women's Trail Race

Trail Run 5 km 10 km
May 2027
May
8
Sa

Camp Mountain Laurel Color Run & Trail Run

Road Race Trail Run 5 km
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