Trail running Race Calendar in Connecticut, United States

Iron Hike - Fall Answer the Bell Ultra Trail Marathon - Basic (Backyard Ultra Format) - 28+ Miles | 14,400'+ Elevation | 24-Hour | Run, Hike or Walk

Cornwall, Connecticut, United States

03 Oct, 2026 (Sat) – 04 Oct, 2026

Free

Trail running

Ultra

Iron Hike - Fall Double Kuwohi Trail Marathon Plus Relay - 28+ Miles | 13,685' Elevation | 24-Hour | Run, Hike or Walk

Cornwall, Connecticut, United States

03 Oct, 2026 (Sat) – 04 Oct, 2026

Free

Trail running

45.1K

Norfolk Land Trust Trail Race Series/Haystack Mountain Challenge

Norfolk, Connecticut, United States

04 Oct, 2026 (Sun)

$25.00 - $35.00

Trail running

5K 10K Half-Marathon

Tackle the Trail (TM)

Northeast, Connecticut, United States

17 Oct, 2026 (Sat)

$75.00 - $250.00

Trail running

Marathon Half-Marathon 10K

Cheshire Community Ymca Harvest Trail Race and Y Cup Relay

Cheshire, Connecticut, United States

24 Oct, 2026 (Sat)

Free - $38.00

Trail running, Running

5K Pumpkin Dash

Hamden Hall Middle School Invitational

Hamden, Connecticut, United States

28 Oct, 2026 (Wed)

Trail running

3.2K

Hamden Hall CISAC League Race

Hamden, Connecticut, United States

31 Oct, 2026 (Sat)

Trail running

5K

Centerville Bank Thompson Turkey Trot

Thompson, Connecticut, United States

08 Nov, 2026 (Sun)

Free - $25.00

Trail running, Walking, Running

5K 3K Kids Fun Run- 12 and under

Storybook Half Marathon

Stratford, Connecticut, United States

21 Nov, 2026 (Sat)

Trail running

Half-Marathon

Frosty Forest 5k

Stratford, Connecticut, United States

19 Dec, 2026 (Sat)

Trail running

5K

Woodland Ramble Trail Run

Mystic, Connecticut, United States

30 May, 2026 (Sat)

Trail running

5K

Camp Challenge

Ashford, Connecticut, United States

16 May, 2026 (Sat)

Trail running

5K