Chestertown
Walking Events Calendar near Chestertown 2026-2027
Monthly updates for Chestertown
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Explore the top walking events near Chestertown for 2026-2027! We've gathered 36 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
The 5K competitive walk is 3.11 Miles, starting at Wyoming Park, Third Street on mostly paved roads through orchards. Water is provided before, during and after; walkers start at the back and the top five men and women receive awards.
August 2026
Walkers can do a 5K at Bohemia Manor Farm Winery along the Bohemia River through vineyard and wooded trails, with water stops and course marshals. Walkers start behind runners and must register with a kindly requested one hour time limit.
Walkers have the choice of 5K, 10K, or 13.1 Miles routes starting at Cedar Lane Regional Park in Bel Air. The event offers a clear course with helpful staff, limited water stations at the end of each lap and at the finish, and EMS is not..
Walkers can choose a 1-mile course at the Maryland Zoo in Baltimore, with the route among zoo grounds and the option to enjoy exhibits afterward. Walk participants receive a tech shirt, bib and finisher medal; add on zoo admission is $15 and tick..
Walkers can take part in the 5K at POLYTECH High School, Walnut Shade Road, Woodside, DE on a course with chip timed results. A COMPETITIVE WALKING category requires walkers to walk the entire distance with no running or jogging and awards honor..
The event includes a 5K walking category starting and finishing at Volunteer Brewing Company, 116 W Main Street, Middletown. The course is a fast, flat residential route and the competitive walking category requires participants to walk the entir..
Walkers can take the 5K course starting at St. Anne's Episcopal School in Middletown DE. The event uses chip timing, offers tee shirts and brunch for sale, awards top three walkers and does not allow dogs.
September 2026
Walkers can choose 5K, 10K, or 13.1 Miles routes starting at 1100 Cedar Ln, Bel Air, MD. The course is clear and lap based; water is limited to the finish area and the end of each lap and staff presence is small.
Walkers can choose the 1 Mile walk alongside the 5k run, starting at 101 College Parkway in Arnold MD. Registration carries a $30 fee and opens 3/4/2026 and closes 5/31/2026.
The event offers walkers a family friendly 1 mile fun walk or a longer 10 km course along the Broadneck Peninsula Trail, starting at East Beach and finishing on the sands of the Chesapeake Bay. Races take place before the festival opens and s..
The Fun Walk is a 1 Miles course that starts at Immaculate Conception School in Towson, MD and follows the event course. Free parking is available in the Ware Ave garage and a virtual walk option runs alongside the running races.
Walkers can join the 1 Mile Fun Run and Walk (1 Mile) or use the scenic courses open to walkers on the 3.2 Miles and 5 Miles routes at Druid Hill Park in Baltimore. The post race festival features music, food trucks and wellness activitie..
Walkers can choose a 1 Mile route or a 3.10686 Miles route alongside the running events. Both start at the UMBC Campus Quad at 1000 Hilltop Circle in Baltimore and follow campus paths around the quad.
Walks start at Sassafras Pavilion in Quiet Waters Park, 600 Quiet Waters Park Road, Annapolis, on park trails and through the Chesapeake Bay front community of Hillsmere Shores. The event includes a walk of 1 to 1.25 miles, held alongside the 5K..
Walkers use the 1 Miles course starting at 1 Safari Place, Baltimore. Varied surfaces mean a jogging stroller is recommended; stroller users should line up in the last race wave and children may join. Same day registration available.
Walkers can choose 1 Mile Bark in the Park or 3.11 Miles on the Fox Trot course at Fair Hill Nature Center in the scenic hills of northeastern Maryland. Parking is in the Upper Covered Bridge lot across from the Nature Center and bibs include..
The 5K starts on the trail by the Middle Branch Park playground and follows waterside and park trails past the Baltimore Rowing Center, Waterview Avenue and Kloman Street. Walkers and stroller participants are welcome; the finish features refresh..
An untimed family fun walk of 1 Miles in Whitehall, starting at 801 Mapleton Ave, Middletown DE on a community route. All registrants will be mailed a commemorative Vet Fest 2026 event T shirt and walkers take part alongside the runs and rides.