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.
September 2026
Walkers can take part in the 5K course alongside the race, with a lively warm up, resident speaker and a family friendly Race Village. There are raffle prizes, awards for top finishers, and a parking lot dance party for those not walking or runni..
The 5K walk starts at 401 Light St in Baltimore and follows a picture perfect course through the Inner Harbor alongside runners. At the finish walkers receive a cup of apple cider, a small pumpkin, a lightweight tech hoodie and a finisher medal.
Walkers can choose the 1 Mile Fun Run/Walk or the 5K course at Honeygo Regional Park in Perry Hall MD. Walking options are 1 Miles and 3.11 Miles, and registrants who want a shirt should register by 8/15.
Walkers can choose a 5K or a 1 Mile Fun Run and Walk at the Maryland Zoo in Baltimore and around Druid Hill Park. Routes take place in the zoo and park setting and run alongside the running races, suitable for casual walkers and families.
October 2026
Walkers can choose 5K, 10K, or 13.1 Miles routes starting at 1100 Cedar Ln in Bel Air, MD on a clear local course alongside the running races. Water is limited to the end of each lap and the race finish and EMS is not on site, so walkers..
Walkers can enjoy an untimed 1K route starting at 5 Bel Air S Pkwy in the heart of Bel Air, MD, alongside the running races. The event includes free parking, a commemorative shirt and access to the festival after the event; registration fee is $1..
The 3.1 Miles 5K walk starts and finishes at Wilmer Park on paved country roads with gentle rolling terrain. Race day packet pickup and registration are available; water at the 5K turnaround and restrooms at start/finish support walkers.
The 1 mile Family Walk starts at The Maryland Zoo and follows a route through the zoo grounds. Strollers are permitted, free parking is available, walkers receive a short sleeved shirt and discounted zoo admission with free admission for children..
Competitive 5K walk at MOT Football and Cheer on Silver Lake Road in Middletown DE, walkers must walk the entire route, chip timed with post race refreshments and a fall fair.
The family fun walk covers 1 Miles and starts at School of the Cathedral, 111 Amberly Way, Baltimore. The walk benefits Mother Seton Academy and has entry fees of $25 for ages 15 and older and $20 for ages 14 and younger.
Walkers follow a 2 miles route starting and finishing at Waverly Brewing, 1625 Union Ave, passing a Tibetan labyrinth, Saint Marys Cemetery and 34th Street lights. On site event day registration only; free to members volunteers and guests, with g..
November 2026
Walkers can take part in a 10K across the eastbound side of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island, starting near 550 Taylor Ave in Annapolis. Walkers participate alongside running races, and race day parking is not ava..
December 2026
Walkers can choose 5K, 10K, or 13.1 Miles courses at Cedar Lane Regional Park in Bel Air. The event uses a clear lap course with limited water stations at the end of each lap and at the finish, and EMS is not stationed on site.
Walkers can choose the 3.11 Miles Run/Walk or the family friendly 1 Miles fun course, both based at Aberdeen Festival Park. The certified, fast and flat course suits walkers of all paces and offers day of packet pickup and mailed packets.
April 2027