And the Scavenger Hunt winners are…

Congratulations winners, and thank you all for participating on Sunday, December 3, 2023.

Each of the winning families were randomly selected and are shown in London Harness with their $825 in gift cards from 33 Wellesley Square stores.

Click each image to expand.

Foley Family of Wellesley
Shown (l to r): Jamie (mom), Keira, Megan, Mosley, Conor and Brian (dad) 

Kaeneman Family of Wellesley
Shown (l to r): Rob (dad), Ilina, Leela, Sneha (mom)

Licata Family of Wellesley
Shown: Liz (mom), Mike, Mike (dad), Fiona and Chandler

White Family of Wellesley
Shown (l to r): Caroline (mom), Nolan, Mike (dad) and Keegan

“This was the first year we’ve done the Stroll…and see new stores I haven’t seen before. This was a real eye-opener of what’s been in the town, as well as stores I haven’t seen or haven’t visited and wouldn’t ordinarily have the opportunity to do so. Thank you very much for putting the Stroll on and introducing me to new stores in the town.”

– Rob Kaeneman


Sunday, December 3, 2023

More than 50 carolers will be strolling throughout Wellesley Square.

Meet Frosty, Rudolph and Barbie as they stroll throughout the Square. You’ll find Barbie in Lower Square, along Washington Street as well as Church Square; Frosty and Rudolph in Upper Square along Central Street.

Pictures with Santa on Central Street.

Holiday Tree Lighting at the Wellesley Square Fire Station, with hot chocolate being served by Dunkin.


Play the Scavenger Hunt with your Smartphone

Pre-register below.

Play Sunday, December 3!

Four (4) winners will be picked, each of which will win $825 in gift cards to Wellesley Square stores.

Winners announced the week of Dec. 4, 2023.

Thank you for supporting our Sponsors

Members of the Wellesley Square Merchants' Association

...who bring you special events like the Holiday Stroll and July Jubilation Sidewalk Sale and Festival.


Act IV Hydration and Wellness
Anderson's Jewelers
B/SPOKE Studios
Bach 2 Rock
Bar Method
Beauty and Main
Beth Urdang Gallery
Boston Veterinary Clinic
CARLA SHAW Sustainable Fashion
Church Square
Choc Allure
Clever Hand Gallery
Coldwell Banker Residential
Dena Pavone Collection
DePrisco Jewelers
Douglas Elliman Real EstateE.A. Davis - Mahi Gold Outfitters
Eileen Fisher
Engel & Volkers
Faber Rug Co.
FIXT Dental
Gibson Sotheby's Int'l Realty
GrettaCole Beauty
GrettaLuxe Fashion
Human Powered Health
Isabel Harvey
J. McLaughlin
J.P. Licks
Kenzie and Hope
Lacrosse Unlimited
LAER Realty Partners
Laughing Monk
Lockheart Restaurant
London Harness
Lux, Bond & Green
Milk Money
Needham Bank
O'Neil Jewelers
Page Waterman, Gallery & Framing
Papa Wheelies

Prepped & Polished
Rotary Club of Wellesley
Rutledge Properties
Salt Boutique
Steve DeMasco's Shaolin Studios
StretchMed Studios
Truly's Ice Cream, Yogurt & Soft Serve
TUMI Wellesley
Tyde with Love
Wellesley Books
Wellesley Holiday Boutique
Wellesley Municipal Light Plant
Wellesley Theatre Project
Wellesley Toy Shop