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 Woodland Ramble Trail Run in Mystic on May 30. Connecticut trail runs run primarily May through December.

Woodland Ramble Trail Run

Sat, May 30 · Mystic, CT Mystic

5K Trail Run

From $31 Open Closing Soon

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

Y Cup Relay5K Trail Race

From $17 Closed

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