Holiday Stroll & Gift Market
All are welcome to the FREE annual Dedham Square Holiday Stroll and Gift Market on the first Friday of December-rain or shine from 5-8pm. Get ready for an evening packed with even more sparkle, joy, and community spirit! The shops will be decorated and brimming with unique gifts and special activities. Carolers voices will fill the air while strolling the 50+ street vendor gift market, food vendors, and a lineup of free holiday fun including a Giant inflatable snowglobe, music performances on the Dedham Town Green, Santa lighting the tree at 6:30pm, pictures with Santa, free activities, model train exhibit and much more!
Explore What’s Happening
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Santa
Get your lists ready! Santa, Mrs Claus and Elfie will arrive at 6:30pm and the magic will begin! Santa will lead the crowd with a carol then light the tree.
Santa and Elfie will head over to TLC Studios (390 Washington St) where you can take your own pictures.
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Food
Food is available in booths on the street, in front of restaurants and inside restaurants.
Full menus are also available for take out and indoor dining.
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Activities
Adults and kids of all ages can find all kinds of fun!
Get your camera ready to take your own pictures inside a giant inflatable snow globe or with Santa and Elfie at TLC Studios, stroll through the Square shops for treats and specials, vote for your fav window display, find the snowflake scavenger hunt and definitely watch 0 scale model trains. And there is so much more! Click the below link for a list.
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Vendors
Stroll and shop over 50 street vendors! From handmade gifts to special treats and everything in between! Businesses and organizations will have treats to give away too.
Looking for food to eat at the Stroll? Click on the “Food” icon.
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High Street (between Washington Street and Harris Ave and Eastern Ave from CVS to High Street) will be closed at 5:30pm and will reopen after 8pm.
Portable bathrooms will be located in the Keystone Lot.
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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
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Holiday Stroll Activities:
Keep checking this growing list of activities!
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Street vendors and businesses giving away promotional materials are encouraged to apply as soon as applications open in the fall. Booth space is limited and always sells out. To be notified when applications open, add your contact information to this form.
Applications and payment are processed through Marketspread.
Food vendors must upload a valid current Certificate of Liability Insurance in Marketspread. Once accepted, then apply for a one permit with the Dedham Health Department by November 6, 2026.
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Sponsoring the Holiday Stroll gives your brand a broad range of exposure to an audience from Boston, Dedham and surrounding communities.
Expected event attendance is is 2,000+. Sponsorship deadline: September 30, 2025.
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After your vendor application is approved by us, food vendors must apply for a one day permit from the Town of Dedham Health Department by Wednesday, November 5, 2025.
Link HERE to apply for a permit with the Dedham Health Department.
Note, Health Permit forms missing information will delay your permit.
Contact:
Dedham Health Department, Town of Dedham, 450 Washington Street, Dedham, MA 02026, 781-751-9220,
Remember to upload your Certificate of insurance naming Dedham Square Circle as additionally insured into Marketspread.
2024 Holiday Stroll before the tree lighting! Courtesy of Paul Chapin.
