Connecticut
Connecticut Walking Events Calendar 2026-2027
Monthly updates for Connecticut
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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!
September 2026
The event offers a 3K walk at Wakeman Boys & Girls Club, Southport, CT, sharing the 5K course for the first half mile before turning south onto Westway. The route is not chip timed, has no awards, and all turns are well marked.
October 2026
Walkers can choose 26.2M 50K 50M 100K or 100 Miles on a 2.5 mile loop at Roosevelt Forest, 700 Peters Lane, Stratford CT, over roots, rocks and rolling hills. The pavilion is the aid station with day and night hydration and snacks and pink..
Walkers can take the 5K route from Race Brook School at 107 Grannis Rd, Orange CT, along neighborhood streets. After the event there are food trucks, live music and community activities alongside the running races.
Healthy Living 1K walk at 81 S Elm St, Wallingford CT alongside the community road races. Registration is online with advance packet or race morning bib pickup, fee $10 and walk shirts for the first 100 walkers.
The 24K (15 miles) walk starts and ends at Jennings Beach in Fairfield, with options to do one 5 mile lap, two laps, or the full beachside loop. Participants pay a registration fee and are asked to raise a minimum of $300.
The Memorial Walk at Bluff Point State Park offers a 2 mile course for walkers, held rain or shine. Registration carries a $30 fee and includes an event t shirt; the walk takes place alongside a Kids' Fun Run.
Walkers may take part in a certified and timed 5K on Keating Farms Ave in Newtown CT alongside the running races in a family friendly setting. The finish area features adoptable and rescued animal ambassadors and a free post race breakfast, and a..
Walk options include a trail route of 3.1 Miles across scenic farm trails and an accessible flat paved option of 1 Miles. Both take place at Gemstone Farm in Wilton CT and include access to the orchard, lake, trails, an event T shirt, food, b..
Miles for Moriah offers a flat, accessible beach boardwalk walk of 5 Miles, starting and ending at Riva on Beach St. The easy paced route features ocean views and welcomes walkers of all ages and abilities, with on site registration.
Walkers complete the 5K course via two loops of the Lime Rock Park circuit in Lakeville CT. The venue provides public restrooms and a water station at start and finish, and wheelchairs and disabled push strollers are welcomed.
Walkers can take the 5K route through scenic Cornwall Green and the Cornwall Valley alongside runners and their dogs. Family friendly activities, live music and food accompany the event and proceeds benefit the Little Guild animal rescue.
Walkers can enjoy the 4th Annual OAH STRIDES at Simsbury Meadows Performing Arts Center with a 5K route and family festival amenities. The event also features a kids 1 Mile fun run alongside the running races and Family Fun Day activities.
Untimed 1.7 mi walk starts at Trumbull High School on the A House driveway near the big lot on a mostly flat route. Strollers and leashed dogs are allowed but dogs must start in back and bring a poop bag; walkers should carry their own water.
Walkers can join the Monster Mile walk; all events start and finish at St. Paul Catholic High School, 1001 Stafford Ave, with free parking via the Maltby Street entrance. Longer courses run through northeast Bristol with a climb at mile 1, roller..
The Madison Memorial Walk is a 2 Miles route at Hammonasset State Park, 1288 Boston Post Road, Madison CT, following park paths. The walk runs alongside the event's running races and supports community programs for grieving children and families.