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Walking Events Calendar near Dedham 2026-2027

Monthly updates for Dedham

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Explore the top walking events near Dedham for 2026-2027! We've gathered 92 great walks in the area. Check out our detailed list below to find your next local walk.

September 2026
The event offers walkers a choice of a 5K over rolling hills through Millis or a 1 mile route on Millis High School grounds at 245 Plain St. Walkers and strollers are welcome alongside the running races.
Walkers may choose a 5K route or a 1 mile kids loop from Shedd Park Pavilion, 453 Rogers St, Lowell. Marked mixed trails and the paved Concord River Greenway are used, crossings are staffed and water is available.
Walkers can use the 5K USATF certified road course that starts and finishes at Burlington High School, 123 Cambridge Street, Burlington MA. Roads remain open with police at intersections, and amenities include a water stop, cider donuts, particip..
Includes a 5K walk from 260 Walden Street, Cambridge, on roads closed for a post race block party with beer garden, food trucks and DJ. Parking is at Danehy Park; number and shirt pick up are available in the days before the event.
Walkers follow a 3.1 Miles country course starting at 148 Peck Street, Rehoboth, MA, with plenty of parking. The family friendly event welcomes dogs, offers free entry for kids under 12, and takes place alongside the 5K run.
The event offers a 1 Mile walk starting at Charles River Center, 59 East Militia Heights Drive, Needham MA. The walk follows the mapped course alongside the 5K run through local roads near the center.
Walkers can choose an in person or virtual 5K in Concord, with course and packet pickup at Concord Carlisle Regional High School. Kids options include 1 mile and 1/2 mile, and entry fees are waived.
October 2026
Walkers can take a 5K road course or a 1K family route from Craft Food Hall BXB at 500 Beaver Brook Rd, Boxboro MA. Ample parking is available; 5K entries include one free drink, and dogs on leash and strollers start behind runners.
Walkers follow a scenic 3.1 Miles course through the backroads of Sudbury, starting and ending at Ephraim Curtis Middle School, 22 Pratts Mill Road. Dogs may walk the route and walkers are offered water and a banana after the event.
The event offers an untimed 5K walk along Carson Beach, beginning at DCR Mother's Rest at 125 William J. Day Boulevard in Boston. Walk categories include adult, youth and CRC patient survivor walkers, with day of packet pick up and registration a..
Walkers can choose the 5K distance on the historic cross country course in Franklin Park near Pierpont Rd in Boston. The event welcomes walkers alongside runners and has registration fees ranging from free for BLS students to $30 for others.
Walkers follow a 5K course that begins at Martha Mary Chapel on the Wayside Inn grounds and offers packet pickup and parking nearby. Water stations and portable bathrooms are provided and strollers are allowed if walkers start at the back of the..
Walkers follow a 4 Miles route starting at 1545 Tremont St, Roxbury Crossing MA. The community event supports the Society of St. Vincent de Paul, features free registration with on site forms, and accepts online pledges to the chosen SVdP council..
Participants walk the 5K at Moakley Park on Columbia Road in Boston with park waterfront views, a water stop near 1.5 mile, two porta potties and a registration tent.
Walkers can take part in the live in person 3.1 Miles (5K) course starting at Barnes Memorial Park in Dedham, MA. The park route is part of a community event with food, drink and music alongside the running races and supports the Dedham Education..
The event offers a 5K fitness walk as two laps of a 1.55 mile loop in Highland Park, Attleboro MA, starting at 104 Mechanic Street. The traffic free course is on wide grass paths with short compact crushed stone sections and pre registered walker..
Walkers can take the 5K course starting at the Knights of Columbus on Nichols Street, following Nichols, Willett Parkway, Westover Parkway, Rugby, Albemarle, Essex and Croydon back to Nichols Street. The route has at least one water station and p..
Walkers will follow a route on Boston Common alongside the 5K run and can enjoy a resource fair, family activities and entertainment around the park. The walk is part of a fundraising event supporting autism research, advocacy and community resources..
Walkers can choose a 5K along the traditional Homecoming route beginning and ending at Lynch Park in Beverly or a shorter half mile fun run for younger participants. Walking and strollers are encouraged and the event is open to everyone; no d..
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