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

August 2026
Aug
15
Sa

Shenipsit Striders Fatass

Trail Run 5 km
September 2026
Sep
12
Sa

Run for the Hills - Niantic

Trail Run 5 km
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep
15
Tu

Charlie Stavros Memorial Beach Run

Trail Run 3 mi
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
Sep
27
Su

Moosup Valley 10K All Trail Race

Trail Run 5 km 10 km
October 2026
Oct
1-4
Th - Su

IronHike Endurance Series

Trail Run 61 mi
Oct
3-4
Sa - Su

Iron Hike - Kuwohi Trail Marathon Plus Relay

Trail Run 28 mi
Oct
4
Su

Nipmuck Trail Marathon

Trail Run 26 mi
Oct
11
Su

Mohawk Mountain Race

Trail Run 5 km 10 km 13 mi 26 mi
Oct
17
Sa

Tackle the Trail - Pomfret, CT

Trail Run 10 km Half Marathon Marathon
November 2026
Nov
1
Su

8 Hours At The Farm

Trail Run 4 mi
Nov
15
Su

Tarrywile Half Marathon

Trail Run 10 km Half Marathon Marathon
Nov
21
Sa

Storybook Half Marathon

Trail Run 13 mi
Nov
26
Th

Soul N Body Thanksgiving Trail Run

Trail Run 4 mi
December 2026
Dec
5
Sa

Tower Tag Challenge

Trail Run
Dec
19
Sa

Frosty Forest 5K

Trail Run 5 km