Artistic rendering – Event may differ
Dedham Square Holiday Stroll & Gift Market
20th annual holiday stroll with 50+ street vendors
About
The 20th annual Dedham Square Holiday Stroll and Gift Market invites visitors to kick off the holiday season with a festive evening. Explore over 50 street vendors offering unique gifts and treats, enjoy live music and caroling, and delight in free activities for all ages. The highlight includes Santa, Mrs. Claus, and Elfie lighting the tree and posing for photos.
Our Take
Family Friendly
Best For
Families and shoppers
Vibe
Festive and community-oriented
Energy Level
Moderate
Budget
FREE
Photo Friendly
Weather Sensitivity
Low
Special Events & Promotions
- Free scavenger hunt with prize
- Photos with Santa, Mrs. Claus, and Elfie
- Vote for favorite business window display
- Free craft for kids
- Free wine tastings at Satellite Bottle Shop
- Free apple cider and cookies at Boston General Store
- Toy donation for Toys for Tots
- Holiday Stroll sushi roll at Uchi Sushi & Ramen
- Mulled spiced wine and trunk show at Terma Goods
- Free passes to Stil Yoga Studio
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.
Location
Event Details
Pricing
FREE
Duration
3 hours
Ages
All ages
Neighborhood
Dedham Square
Timed Entry
No
Featured Performers
- Dedham High School band
- Dedham School of Music
- First Church & Parish Dedham Carolers
- Miss Massachusetts, Kiersten Khoury
- Terma Goods DJ
Organizer
Dedham Square Circle
Practical Information
Parking
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. A parking map is available.
Pet Policy
No pets allowed
Food & Drink
Food is available in booths on the street, in front of restaurants, and inside restaurants. Full menus are available for take out and indoor dining. Festive food and warm beverages from local vendors.
Quick Actions
Tips & Advice
- Arrive early to find convenient parking, especially if you plan to visit popular attractions like Santa or the model train exhibit.
- Check the 'Activities List' link for the most up-to-date schedule of performances and special offerings before you go.
- Bring a toy donation for Toys for Tots at Oscars to spread holiday cheer while enjoying the festivities.
- Dress in layers as the event is outdoors and takes place in the evening, even if it's 'rain or shine'.
- Take advantage of the free craft for kids at the DSC craft table, available from 5-7pm.
Frequently Asked Questions
What time does the Holiday Stroll start and end?
The event kicks off the holiday season on the first Friday of December from 5:00 PM to 8:00 PM.
Is there an admission fee for the Holiday Stroll?
No, the Dedham Square Holiday Stroll is a free event for all attendees.
Where can I find parking during the event?
Free street parking and several designated parking lots are available, including the Keystone Lot and Town Hall Parking Lot. A parking map is provided.
What kind of vendors can I expect to find?
You can browse over 50 street vendors offering a variety of handmade gifts, special treats, and artisanal products.
What activities are available for children?
Children can enjoy a free craft at the DSC table, a scavenger hunt, pictures with Santa, and a model train exhibit.
