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 Run for The Hills in Niantic on September 5. Connecticut trail runs run primarily September through June.

Run for The Hills

Sat, Sep 5 · Niantic, CT Niantic

Run for the Hills

From $25 Open Closing Soon

Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Wed, Sep 16 · Cheshire, CT Cheshire

5K Trail RaceY Cup Relay

From $17 Open

17th Annual Farmington River Run 5K Trail Race

Sun, Sep 20 · Farmington, CT Farmington

5K Trail Run

From $35 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 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

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

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

Hartford Track Club 8K Cross-Country Challenge

Sun, Nov 22 · West Hartford, CT West Hartford

8K Cross Country Race

From $25 Closed

Frosty Forest 5k

Sat, Dec 19 · Stratford, CT Stratford

Frosty Forest 5k

Closed

Woodland Ramble Trail Run

Sat, Jun 5 · Mystic, CT Mystic

5K Trail Run5K Trail Run

From $31 Open