Dedham Square Holiday Stroll & Gift Market
Visitors can browse an open-air market with more than 50 street vendors offering gifts and treats, alongside local shops decorated for the holidays. Santa, Mrs. Claus, and Elfie arrive to lead carol singing and light the town tree before taking photos at TLC Studios. Other activities include stepping inside a giant inflatable snow globe, enjoying live music on the Dedham Town Green, and viewing an O scale model train exhibit.
Fri, Dec 4, 2026 All ages Free admission.
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Plan Your Visit
Hours
5-8pm; Santa, Mrs Claus and Elfie arrive at 6:30pm, and Santa leads a carol before lighting the tree.
Neighborhood
Dedham Square
Food & Drink
Food is available from street booths and in front of restaurants, as well as inside restaurants, with full menus available for takeout and indoor dining.
Parking
Free parking is available on the street and at Keystone Lot, Lower Gonzalez Lot, Upper Gonzalez Lot, and Town Hall Parking Lot. Public transportation options listed include the 34E bus and the Endicott and Dedham Corporate commuter rail stations.
Location
Tips & Advice
- Be near the tree when Santa, Mrs. Claus and Elfie arrive, since Santa leads the crowd in a carol before lighting the tree.
- Head to TLC Studios on Washington Street after the tree lighting to take your own photos with Santa and Elfie.
- Dress for an evening outdoors on High Street, because the stroll goes ahead rain or shine.
- Expect High Street and part of Eastern Ave to close to cars during the stroll, so use the free lots or the 34E bus.
- Remember that the portable bathrooms are in the Keystone Lot, which is also one of the free parking lots for the stroll.
Links & Contact
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.
Frequently Asked Questions
Where can I park?
Free parking is on the street and in the Keystone Lot, Lower Gonzalez Lot, Upper Gonzalez Lot and Town Hall Parking Lot. The 34E bus and the Endicott and Dedham Corporate commuter rail stations are also options.
Where can we get pictures with Santa?
After the tree lighting, Santa and Elfie head to TLC Studios at 390 Washington St, where you can take your own pictures.
Where can we eat?
Food is sold from booths on the street, in front of restaurants and inside restaurants, and full menus are available for takeout and indoor dining.
What is there for kids to do?
Kids and adults can take pictures inside a giant inflatable snow globe, look for the snowflake scavenger hunt, vote for a favorite window display, watch O scale model trains and catch music on the Dedham Town Green.
How do I become a street vendor?
Applications open in the fall and are processed through Marketspread. Booth space is limited and always sells out, so join the notification list. Food vendors also need a liability insurance certificate and a one-day Dedham Health Department permit.
Browse Christmas in Dedham
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.