Dedham Square Circle’s Summer Stroll
Get ready for the 2026 Summer Stroll event on Thursday, July 16 from 6-9pm (rain date July 23) in Dedham Square.
As the day winds down, the Dedham Square streets shut down to vehicle traffic and open up to foot traffic, live music, street vendors, food, Roundhead Brewing Co. beer garden, activities, and shopping Square businesses and street vendors. Stroll, eat, drink, relax, and listen to music under the stars. There will be fun and games for kids & adults and the event is free to attend.
Live music on High St will get you grooving while you enjoy more than street vendors, food vendors and outdoor dining options. Want to just hang our and watch the music? Bring a chair!
The fun keeps going after 9pm with more live music, movies at the Dedham Community Theatre, and plenty of places to eat, drink, and relax in Square restaurants and bars (outdoor and indoor)! To view the Dedham Square business directory, click here.
Interested VENDORS go here.
FREE ACTIVITIES
live music
yard games for adults and kids on the Town Green
face painting for kids
kids temporary tattoos
kids craft
sink the shot basketball game
chalk art zone
Explore What’s Happening
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2026 Music
The A-Beez - 6:30-9 @ Main Stage in Dedham Square.
Jonny Goes To Boston 6-6:30, and 7:30-8 on the 2nd stage 3 Eastern Ave, Dedham Square.
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2026 Food
Food is available in booths on the street, in front of restaurants, inside restaurants and outdoor dining.
Restaurants will offer select menu items to-go in front of their shops. Full menus are also available for take out, indoor and outdoor dining.
The picnic area and Vine Garden garden are located near the main stage.
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2026 Drink
New this year! Enjoy live music in the Roundhead Brewing Company beer garden located on Eastern Ave near the 1st & 2nd stages and food. Adults 21+ with valid ID can enter. Street vendor food is also allowed.
Looking for more non-alcohol options? All street food vendors can quench your thirst.
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2026 Vendors
Stroll and shop street vendors and businesses! From artisans of handmade gifts to treats and everything in between! Last minute additions added weekly so keep checking back.
Looking for food to eat at the Stroll? Click on the “Food” icon.
Additional Details
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MAP of Free Parking Lot Locations
Public transportation:
-Dedham has 2 Commuter Rail Stations: Endicott and Dedham Corporate. Both are a short Uber/Lift ride or 30 min walk. Schedules can be found here.
Free parking can be found on the street or in the following parking lots:
-Keystone Lot, 10 Eastern Avenue
-Lower Gonzalez Lot, 351 East Street
-Upper Gonzalez Lot, 420 Providence Highway
-Town Hall Parking Lot, 450 Washington St
-Parking lot across from VFW at 95 Eastern Avenue
-Registry of Deeds Lot, 282 Ames Street
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The following streets will be closed to traffic during the Summer Stroll:
High Street between Washington and Harris Streets and Eastern Avenue between CVS and High Street will be closed to vehicular traffic from 5:30 to 10:30pm.
Please plan accordingly.
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Portable bathrooms will be located in the Keystone Lot. (corner of High St. and Eastern Ave)
A Picnic/Seating area will be a centrally located in the middle of the street.
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Dedham Square is home to over 120 businesses from food, retail, services recreation to so much more!
Visit our business directory here for a full listing.
Sponsors
View Sponsor Opportunities Here.
This program is funded in part by a grant from the the Mass Cultural Council, a state agency.