Connecticut
Connecticut Walking Events Calendar 2026-2027
Monthly updates for Connecticut
Get new running races (and updates) in your inbox every month.
Explore the best walking events in Connecticut for 2026-2027! Our updated list features 89 great walks across the region. Find your next walk in Connecticut below and join the walking community at these great events!
December 2026
The 2 Mile walk begins on the Bethlehem Town Green in front of Memorial Hall and follows the 5K course on rolling country roads, turning back at the one mile mark. Parking is at the Bethlehem Fair Grounds with shuttle buses to the Green, and the..
Walkers can join the 3.1 Miles course alongside the running races, starting at 370 Bassett Road, North Haven, CT. Walkers receive a shirt, jingle bells, and a medal.
Walkers can complete the 5K out and back course starting at 10 Washington Parkway in Stratford along a flat scenic waterfront in the Lordship section. The family friendly route suits all abilities and collects new, unwrapped toy donations at bib..
Walkers can complete the 5K on forest trails at Roosevelt Forest, 700 Peters Lane, Stratford CT, following an off road wooded route that requires a little trail experience. The pavilion is the sole aid station; parking is limited and larger vehic..
January 2027
The event includes a 2 Miles walk in Milford, CT, held alongside the 5 Mile race. Route and terrain details will be announced later.
February 2027
Walkers may register to walk the scenic 7.8 miles loop around glacial Lake Waramaug, starting and finishing at Hopkins Vineyard with lake shore views. The course is mainly flat with gentle rolling hills and a final 0.2 miles ascent up Hopkins..
April 2027
Walkers can choose 5K, 10K, or a 4 hour option on the 3.2 mile loop at Lake Mohegan, Fairfield CT. Trails are runnable and varied. Water at start finish for 4 hour and 10K; no on course aid for 5K and event is cupless.
May 2027
Walkers can take part in the 5K in Hartford, following the first loop with the option to complete the second loop alongside the running race. Event offers live online results and free video and same day finish line photos for participants.
The untimed Fun Run/Walk of 3.1 Miles follows the Shepaug River through Steep Rock Preserve with a gradual incline. It starts at 2 Tunnel Road, Washington Depot CT; walkers will not receive a race bib.