Newtown
Walking Events Calendar near Newtown 2026-2027
Monthly updates for Newtown
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Explore the top walking events near Newtown for 2026-2027! We've gathered 66 great walks in the area. Check out our detailed list below to find your next local walk.
September 2026
Walkers can complete a 5K in person at St Francis Episcopal Church, 2810 Long Ridge Rd, Stamford CT, on a USATF certified course with canine companions welcome. A virtual 5K is available Sept 14 to 20 for remote participation.
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 walkers a scenic loop along Pear Tree Point Beach in Darien with options for 1.5 Miles or 5 Miles, alongside the running races. Parking is limited so carpooling, biking, or walking is encouraged, family friendly activities ar..
Walkers can join a 5K course at Sherwood Island State Park in Westport alongside the running races. No dogs or alcohol are permitted and there is no on-site registration; children 9 and under register free and family pricing is offered.
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 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..
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.
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 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.