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Walking Events Calendar near Worcester 2026-2027

Monthly updates for Worcester

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Explore the top walking events near Worcester for 2026-2027! We've gathered 38 great walks in the area. Check out our detailed list below to find your next local walk.

July 2026
Walkers have a mostly flat family friendly 5K route from Upton VFW in Upton, MA, ideal for a family walk before it gets too hot. Day of registration opens at 7am, with a water stop at halfway and parking at the VFW and Rose Garden.
The event welcomes walkers on the 5K course from 175 Lincoln Street in Blackstone MA with race day parking. Strollers start in the back; dogs are not allowed and service animals are permitted with prior arrangement.
Walkers follow historic trails at Minute Man National Historical Park in Lexington and Lincoln, MA along routes used by Colonial Militia and British forces. The ruck offers a walking option and starts at 210 North Great Road in Lincoln, 22 miles from..
August 2026
Walkers follow a 3 Miles route in downtown Worcester from 64 Franklin Street, passing through the Canal District and downtown streets alongside the official 5K course. The stroller friendly walk is open to all ages; walkers pay $10 and are entere..
Walkers follow a family friendly 3.1 Miles course from South Street across from the Police and Fire Station through hilly and flat sections. Warm ups occur beforehand and parking is at Meetinghouse School and nearby lots.
September 2026
The event offers walkers a USATF certified 5K run/walk that starts and finishes at Walpole High School. Strollers are welcome at the back of the starting pack and dogs are not allowed on the course for safety.
Walkers can choose a 5K or an untimed 1 mile route through scenic Hopkinton State Park at 164 Cedar St, Hopkinton, MA, on pavement with some rolling hills. The course is fully wheelchair accessible and welcomes strollers, wagons, and wheelcha..
Walkers can use the 5K course at 82 Wheelock Ave, Millbury, featuring three short hills in the first half, a fast downhill and a flat finish. Start and finish are adjacent to parking and number pick up and registration, and pets on a leash and st..
Walkers can join the scenic 5K (3.15 Miles) lap around Alexander's Lake, starting and finishing at The Lake Tavern in Dayville on private roads. Race day registration, check in and bag and bib pick up are available, with a kids fun run alongside..
Walkers can use the 5K course starting and ending at Moon Hill Brewing Co., Parker Street, Gardner, MA alongside Oktoberfest activities. First beer provided with registration is served after the course and awards honor the top 3 M/W/N walkers.
Walkers can follow the 5K road course beginning at 33 Howard Street in Northborough, MA alongside runners, with bananas and water provided.
A community fundraising walk of 3 Miles along the Assabet River Rail Trail starting at Immaculate Conception Meehan Hall, 119 Washington St., Marlborough. Walkers may complete the full distance or shorter routes, registration is free and extra fo..
Walk a 3.1 Miles 5K route at Smoke Crest Farm and animal sanctuary from 830 Springhill Rd, Barre MA, alongside a community health fair with resource booths and educational presentations. Pre registration is $15 and day of event is $20 for the 5K;..
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 can choose a 2.5K single loop or 5K double loop starting on the track at Shepherd Hill Regional High School, 68 Dudley Oxford Rd, Dudley MA. Course mixes road and grass; porta potties and bathrooms on site and parking.
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 follow the distance 3 Miles (also described as 5K or 3.5 mile) starting and finishing at The Corner Dive. Entry is free and walkers are welcome alongside the running races with post event drinks and music.
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.
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