Rise + Shine Marketplace
Winchester Town Hall 71 Mt. Vernon Street, Winchester, MAWelcome to Rise + Shine Marketplace where shoppers rise & makers shine! We are thrilled to welcome you with open arms and share the talent we have gathered for you...
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ENKA Society Turkey Trot
Skillings Road, Winchester Winchester, MA, United StatesEnKa’s 3rd Annual Turkey Trot 3.1 miles / 5 k fun for the whole family! Start a new Thanksgiving tradition! You can walk, trot, or run! Here is the link to sign up...
1st Annual Gingerbread Decorating Contest
Winchester Center Winchester, MAAs you stroll and shop around Winchester's Historic Town Center, vote for your favorite Gingerbread House. Houses will be displayed throughout stores for online voting--the community decides the winner! VOTE...
Trolls on the Stroll Scavenger Hunt
Winchester Center Winchester, MAHow to play: Find all six pairs of trolls hidden in stores listed Get a signature from the store once the trolls are found Once your passport has been signed...
2nd Annual Stroll Weekend Schedule
Winchester Center Winchester, MAKick off the holiday season in style! Winchester's Second Annual Holiday Stroll Weekend offers a slate of events sure to entertain and enjoy all that Winchester has to offer. We...
Holiday Shop + Stroll
Winchester Center Winchester, MAKick off your Holiday shopping season in style!This year’s Shop + Stroll event will feature a stylish line-up of independently owned shops, boutiques, pop-ups, food, drink and entertaining festivities that...
Winchester Holiday Tree Lighting Celebration
Town Common Winchester, MA
Nutcracker to Go
Get in the Holiday Spirit and join The Ballet Arts Center for this FREE and fun event on Saturday, December 3rd at Winchester Town Hall as part of the Holiday Stroll!...
Yule Ball at Book Ends
Join the staff at Book Ends on Saturday, December 3rd, from 3-6 pm for the first annual Yule Ball! Six local authors will be present: Dick Lehr, Eric Joy Donlin,...
“Best in Stroll” Dog Parade
Town Common Winchester, MABring the kids and your fur babies to this fun event where the star of the show are the furry ones! Dress up in costumes, practice those tricks and meet...
Santa comes to Winchester!
McCall Middle SchoolPut the kids in the car and head out to meet Santa! Cars will line up on Mystic Valley Parkway and enter behind McCall Middle School. Decorate your car, dress...
The Holiday House Tour
Winchester, MAThe Holiday House Tour is back! Join us for this very festive event and view the amazing decorations of six of Winchester's houses. Tickets may be purchased at Book Ends...
