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Rise + Shine Marketplace
Rise + Shine Marketplace
Welcome 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
ENKA Society Turkey Trot
EnKa’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...
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The Red Ticket Raffle 2022!
The rules are simple: for every $25 spent at a participating Winchester Chamber of Commerce store, shoppers will receive a “Red Raffle Ticket” that automatically enters the shopper into a...
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1st Annual Gingerbread Decorating Contest
As 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...
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Trolls on the Stroll Scavenger Hunt
How 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
Kick 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
Holiday Shop + Stroll
Kick 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...
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Nutcracker to Go
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!...
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Yule Ball at Book Ends
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,...
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“Best in Stroll” Dog Parade
“Best in Stroll” Dog Parade
Bring 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...
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Santa comes to Winchester!
Santa comes to Winchester!
Put 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...
