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!
October 2026
Walkers follow a 5K course through the Griffin Hospital neighborhood, starting at 350 Seymour Avenue in Derby, CT. The non competitive, family friendly event offers same day registration and includes a race t shirt for participants.
Walkers follow the 5K course of 3.1 Miles starting at Andover Elementary School, 35 School Rd, Andover CT, on a community route alongside the running race. Event includes bib pick up and a Halloween costume contest, with proceeds supporting local..
Walkers take the 4K course from Jimmy Lee Stadium at Crosby High School, on a challenging up, down and flat route around the track and grounds. Parking is in the lots right of the Rotella Magnet School entrance across from the track and packet pick..
The 1 Mile Fun Walk starts at the Farmington Canal parking lot on Sherman Ave in Hamden, CT. The walk takes place alongside the event's 5K and 10K running races.
The event offers a Halloween themed 1 mile fitness walk through the picture perfect Farmington River Valley with views of Simsbury and the Farmington River. It welcomes walkers of all abilities and includes fitness activities, healthy snacks, giv..
Walk the scenic 5K course from 5 Indian Neck Avenue in Branford, CT, along water views and autumn scenery. Finish line treats include a freshly baked cider donut and a beverage from New England Brewing Company for those 21 and over with valid ID..
Walkers follow a 5K route on the Collinsville rails to trails bike path, starting near the Crown and Hammer at the Collinsville Bike Path walking bridge by Town Hall with a halfway turnaround. Strollers are permitted and no wheels like bicycles o..
November 2026
Walkers can choose a 3 Miles live or virtual walk starting at 172 Lake Street, Coventry CT. The event runs alongside running and ruck options and donates 100% of proceeds to CT veteran organizations.
Walkers can complete a 5K course starting at 1 School St in Bethel, CT as part of the event's Run/Walk. Registration opens 3/2/2026 and fees apply, with a reduced rate for first responders, active duty military and veterans.
A Fitness Walk covers 1 Miles and starts at 2016 to 2098 Hillside Rd, Storrs, CT. The walking only event runs alongside the 5K and 10K races and follows roads around the start area.
Walkers follow the hilly half marathon route in a timed 4 Miles loop starting at American Legion Post 27 in Litchfield. The walk is timed, uses the same course as the races and includes runner amenities and a finish beer.
Walkers can choose a 1 mile walk or join the 5K course starting at Norton School in Cheshire, CT, following the scenic Farmington Canal Line past historic homes. Walkers are not timed; first 550 5K or walk entrants get a long sleeve tech shir..
At Tarrywile Park in Danbury walkers can choose 10K, Half Marathon, or Marathon on a looped, technical single track with close to 3K elevation and lakes and viewpoints. Aid stations are on course but walkers must carry their own cup or bo..
Walkers are welcome on the 13.1 miles trail at Roosevelt Forest, 700 Peters Lane, Stratford CT, consisting of eight 1.64 mile wooded loops on marked singletrack and doubletrack with roots, rocks and rolling hills. Aid station and porta potties ar..
Walkers follow a 3.5 Miles loop around Scoville Reservoir on the Mill Pond Way Trail near 201 Nichols Road, Wolcott. Free water, light snacks and a porta potty are provided and post race yoga is available for participants.
Marked routes of 3+ miles, 2 miles and 1 mile run on sidewalks and welcome strollers and leashed pets. Routes start at Fowler Pavilion behind the library and go past Gulf Beach; roads stay open so walkers must follow street laws.
The event offers a 5K road loop that starts at Bethel Municipal Center in downtown Bethel and goes through the town neighborhoods. The course is moderately uphill in the first half and downhill in the second half, with the first and last one thir..
A road walk of 5K starting and finishing at Redding Community Center on Lonetown Rd (RT 107). This walking only event has a $35 registration fee and registration runs 5/1/2026 to 10/31/2026.
Walkers can choose the dedicated 2.5K fitness walk starting and finishing at Newtown Middle School on routes introduced in 2019. Water and coffee are available; packet pickup is at C.H. Booth Library before the event.
A casual 2 Mile walk at the Branford Thanksgiving 5K event starting at Walsh Intermediate School, designed for all ages and abilities. The event uses a flat, scenic course through Route 146 and Pine Orchard Golf Course and includes pre and post r..