Trail Runs in Connecticut 2026 | Upcoming Races & Dates | My Next Race

There are 13 trail runs in Connecticut scheduled for 2026. The next is the 11th Annual Flanders Field & Forest 5K Trail Run/Walk in Woodbury on June 5. Connecticut trail runs run primarily June through December.

11th Annual Flanders Field & Forest 5K Trail Run/Walk

Fri, Jun 5 · Woodbury, CT Woodbury

Flanders Field & Forest 5K Run/Walk

From $30 Open Closing Soon

Centurion Trail 33 Hour Ultra

Sat, Jun 27 · Stratford, CT Stratford

Centurion Trail 33 Hour Ultra

Closed

Run for The Hills

Sat, Sep 5 · Niantic, CT Niantic

Run for the Hills

From $25 Open

Where the Pavement Ends Single & Double Loop

Sun, Sep 20 · Ridgefield, CT Ridgefield

Where the Pavement Ends - Single LoopWhere the Pavement Events - The Double (two loops)

From $42 Open

Cockaponsett Trails to a Cure

Sun, Sep 20 · Chester, CT Chester

Cockaponsett Trails to a Cure- 4 milerCockaponsett Trails to a Cure- 9 miler

From $20 Closed

17th Annual Farmington River Run 5K Trail Race

Sun, Sep 20 · Farmington, CT Farmington

5K Trail Run

From $35 Open

Forbidden Forest 30 Hour Ultra

Sat, Oct 3 · Stratford, CT Stratford

Forbidden Forest 30 Hour Ultra

Closed

Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

Sun, Oct 4 · Norfolk, CT Norfolk

5K Trail Race10K Trail RaceHalf Marathon

From $25 Open

Tackle the Trail (TM)

Sat, Oct 17 · Northeast, CT Northeast

Individual - 10KIndividual - Half MarathonRelay Team - Marathon +1

From $45 Open 45 spots left

Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Sat, Oct 24 · Cheshire, CT Cheshire

5K Trail RaceY Cup Relay

From $17 Open

Centerville Bank Thompson Turkey Trot

Sun, Nov 8 · Thompson, CT Thompson

Thompson 3K Wobble- Walk- untimedThompson 5K Trail Run

From $25 Open

Storybook Half Marathon

Sat, Nov 21 · Stratford, CT Stratford

Storybrook Half Marathon

Closed

Frosty Forest 5k

Sat, Dec 19 · Stratford, CT Stratford

Frosty Forest 5k

Closed