Litchfield
Walking Events Calendar near Litchfield 2026-2027
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Explore the top walking events near Litchfield for 2026-2027! We've gathered 43 great walks in the area. Check out our detailed list below to find your next local walk.
Walkers can choose 3.1 Miles or 8 Miles routes starting on New Milford Town Green. The course follows scenic rural roads with rolling hills including Canterbury Hill, provides water stops, and welcomes walkers and dogs.
August 2026
Walkers can take part in a 5K health walk that starts at Holy Trinity Orthodox Church on Joe's Hill Rd in Danbury, CT, alongside the running races. Race day registration and check in are at the church and pre registered walkers may receive a T sh..
Walkers can take the 2 Mile route through the Fitzgerald Cornfield at 112 Beecher Road, Woodbridge CT, with ample parking at the Cornfield lot, Beecher Road and Meetinghouse Lane. Refreshments, a verified time, awards and event t shirts are provi..
Walkers have a 2.85 Mile walk that starts and finishes in Coe Park, Torrington, CT, on the road race course. Entry fees are $30 preregistration, $40 after, and $10 for 18 and younger; the walk runs alongside the running races.
Walkers use a certified 5k (3.1 Miles) course starting at Pent Rd Recreational Complex in Beacon Falls. Entry fees are $25 for adults and $10 for 16 and under, and the walk takes place alongside the running races.
Walkers can choose a 1.5 Miles route or tackle the 5K course starting and finishing at Millbrook Vineyards & Winery, across mostly grass cross country terrain with some mildly challenging sections. Registration includes a post walk pour of wi..
The event offers a 5K walk starting at The Amber Room Colonnade in Danbury, with a scenic route across the Amber Room grounds. Walkers join alongside the running race and can enjoy a post race barbecue and refreshments on site.
Walkers can join the 5K walk on a scenic, flat course starting at 6 Youngs Field Rd, New Milford CT, alongside the running races. The route includes a hydration station and post race refreshments, and registration is free.
September 2026
Walkers can join the certified 5K course at Fairfield Hills, 3 Primrose St, Newtown, CT, on event day. Entry is $30 plus three canned goods for the main walk and $5 plus three canned goods for the kids walk, held alongside the running races.
At Macedonia Brook State Park walkers can choose 12K, 25K or 50K single track routes with climbs, technical descents and viewpoints. Aid stations have water and snacks but walkers must carry a cup or bottle due to a cupless policy.
The Memorial Walk is a 2 mile route at Winding Trails in Farmington along Memory Lane, held alongside a Kids' Fun Run. Walkers can expect a family friendly route with activities and optional custom memorial signs.
Walkers can choose the 2 Miles Family Fitness Walk starting at 360 Amity Road on the JCC campus, with a course winding through Woodbridge residential neighborhoods. Free on site babysitting for children ages 2 to 8 is available during the races and..
The event offers a 5K scenic Middlebury route starting and finishing at Pies & Pub, 1 Store Road, Middlebury CT. The family friendly course is chip timed, provides free pizza for all finishers and free beer for 21 plus, with parking at Meadowview P..
Walkers can take the 1 Miles route at Edgewood Park in New Haven on a nicely shaded course ideal for September. Ages 1 to 12 walk free with registration, ages 13 to 18 pay $12 and adults $25, and free lunch is provided to participants.
The 5K walk starts and finishes at the Hartford HealthCare Community Stage at Mortensen Riverfront Plaza, following the Connecticut River through Riverfront Recapture parks. Terrain includes dirt and wooded trails, grass and paved walkways and fr..