Glen Doherty Memorial Road Race
This is a race to honor our hometown hero Glen Doherty. Glen was a former Navy SEAL who sacrificed his life in order to save other people. Winchester helped to...
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Bespoke of Winchester Open House
Bespoke of Winchester 25 Thompson Street, Winchester, MAJoin Melina Guglietta of Bespoke Winchester to hear all about the design-build-install process and get useful tips for updating and decorating your house this Fall. Registration is free, but required...
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...
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...
The Red Ticket Raffle 2022!
Winchester Center Winchester, MAThe 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...
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,...
