Holiday Stroll & Gift Market

The 18th annual Dedham Square Holiday Stroll is a free event that kicks off the holiday season on the first Friday of December-rain or shine from 5-8pm. This year will be bigger, brighter, and more festive than ever! Get ready for exciting new additions including a 50+ street vendor gift market, food vendors, and a lineup of free holiday fun including Santa, Mrs Claus and Elfie lighting the tree at 6:30pm, pictures with Santa or inside a Giant inflatable snow globe, foam snowball throw, carolers, model train exhibit and much more! Updates are being added weekly to the Activities and Specials listing below.

Note-Pictures with Santa will be at Keshar Indian Restaurant (next to Ron’s Inc Cream) 557 High St.

Explore What’s Happening

  • 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, Mrs Claus and Elfie will head over to a (new location) Keshar Indian Restaurant at 557 High St (next to Ron’s Ice Cream) where you can take your own picture.

  • 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.

    Food Options

  • Activities

    Adults and kids of all ages can find all kinds of fun! Check out the Map here.

    Get your camera ready for the perfect picture of you inside a giant snow globe, test your aim at the foam snowball throw, stroll through the Square shops for treats and specials and definitely watch 0 scale model trains. And there is so much more!

    Activities

  • Vendors

    Stroll and shop over 50 street vendors! From handmade gifts to special treats and everything in between!

    Looking for food to eat at the Stroll? Click on the “Food” icon.

    Street Vendors

  • Holiday Stroll Activities:

    • Get inside a Giant Snow Globe and take holiday pictures

    • Live music: 5-5:30 Band Gig, 6:00-6:30 Dedham High School band & Dedham School of Music

    • First Church & Parish Dedham Carolers will be caroling around the Square

    • Santa Mrs Claus and Elf arrive to light the tree at 6:30pm

    • 6:45pm - after the tree lighting, Santa, Mrs Claus & Elf will head over to Orchid 7 where you can take pictures with them

    • Visit Square businesses for treats and special offers

    • A free craft for kids will be at the DSC craft table from 5-7pm

    • Meet Miss Massachusetts, Kiersten Khoury (from Westwood!!!).

    • Toy and Model trains on display at the Dedham Museum & Archive (612 High St) on Friday 5-8pm and Saturday 10-2.

    • Boston General Store (626 High St) free apple cider, cookies & Alpine old Fashioned drinks. Don’t forget to drop off a letter to Santa to the special mailbox.

    • Bring a toy and your appetite to Oscars (380 Washington St)! and drop off a donation for Toys for Tots.

    • Stop by JamZone (597 High St) to see some singer/song writers in action and take a tour of the facility

    • Uchi Sushi & Ramen (545 High St) will have a Holiday Stroll sushi roll.

    • The Dedham Exchange (445 Washington St) will have a street vendor booth at the Stroll with Dedham theme items and coupons for the store

    • Stop by A New Gopen Optical (584 High St) for a treat!

    • Try a freshly made savory or sweet crepe at LaLuce (591 High St).

    • Stroll the art on display at the newly opened Gallery 593 (593 High St).

    • Stop by Essential Advanced Skincare and Medspa (358 Washington St) for light snacks and a special treat!

    • Satellite Bottle Shop (578 High St) will have free wine tastings.

    • Start your holiday shopping at Love and Grace Girls (3 Harris St). Serving a fun refreshment and treats. Open until 8pm.

    • Terma Goods (644 High St) will have a live DJ, mulled spiced wine, trunk show, free passes to Stil Yoga Studio and free signature gift wrapping. Open til 8pm.

    More activities added weekly!

  • 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.

  • Public transportation:

    -34E bus

    -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 Map

  • Street vendors and businesses giving away promotional materials apply HERE for booth space at the Holiday Stroll. Space is limited.

    Applications and payment must be received by November 12, 2024.

    Food vendors must apply for a permit with the Dedham Board of Health AND provide us with a current Certificate of Liability Insurance.

  • After your vendor application is approved, food vendors must apply for a health permit from the Town of Dedham Board of Health Department by Thursday, November 6, 2024.

    Complete and return the Board of Health permit form with $50 fee to the Dedham Health Department. Forms missing information will delay your permit.

    Health Permit Memo

    Health Permit Form

    Contact:

    Kylee Sullivan, Health Director, Town of Dedham, 450 Washington Street, Dedham, MA 02026, 781-751-9220, KSullivan@dedham-ma.gov

    Remember to upload your Certificate of insurance naming Dedham Square Circle as additionally insured into Convention Force.

  • 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 2,500+. Sponsorship deadline: October 15, 2024.

    Holiday Stroll Sponsorship Packet

Holiday Stroll Sponsors