Trail Race · Connecticut
Trail Races in Connecticut
Every trail race we track across Connecticut, sorted by date. Each card shows deterministic 0–100 scores for beginner-friendliness, PR potential, value, vibe, and family appeal.
Other
Sat, May 16, 2026
Stratford, Connecticut
trail
Rolling
30PR40value40vibe
5K
Sat, May 30, 2026
Mystic, Connecticut
trail
Rolling
35PR40value45vibe
Other
Sat, Jun 20, 2026
Hebron, Connecticut
trail
Rolling
30PR40value30vibe
Ultra
Sat, Jun 27, 2026
Stratford, Connecticut
trail
Rolling
30PR40value45vibe
Other
Sun, Sep 20, 2026
Ridgefield, Connecticut
trail
Rolling
30PR40value50vibe
scenic
Ultra
Sat, Oct 3, 2026
Stratford, Connecticut
trail
Rolling
30PR40value45vibe
Marathon
Sat, Oct 17, 2026
Northeast, Connecticut
trail
Rolling
30PR40value45vibe
Half Marathon
Sat, Nov 21, 2026
Stratford, Connecticut
trail
Rolling
30PR40value45vibe
5K
Sat, Dec 19, 2026
Stratford, Connecticut
trail
Rolling
35PR40value65vibe
costume
festive
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Top metros in Connecticut for trail races
Cities in Connecticut with the most trail race races on the calendar.