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The Red Ticket Raffle 2022!

Winchester Center Winchester, MA

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...

1st Annual Gingerbread Decorating Contest

Winchester Center Winchester, MA

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...

Trolls on the Stroll Scavenger Hunt

Winchester Center Winchester, MA

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

Winchester Center Winchester, MA

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...

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, MA

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...

Santa comes to Winchester!

McCall Middle School

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...

The Holiday House Tour

Winchester, MA

The 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...

Uke-a-Palooza Concert

Winchester Community Music School 470 Highland Avenue, Winchester, MA

More than 25 ukulele students of all ages will hit the stage to perform toe-tapping tunes from folk to Americana to pop & rock. Under the direction of WCMS faculty...

Women in Business Networking Event

Krave Kitchen & Bar 348 Cambridge Road, Woburn, MA

Are you a woman in business who is looking to grow your business or be more known across the Greater Winchester area? If so, join us for this fun and...

The Inside Scoop in Interior Design with Kate Maloney

Kate Maloney Interior Design 4 Mt Vernon Street, Winchester, MA

Are you embarking on a home renovation and don't know where to start or how to assemble a team?  Have you ever wondered what interior designers do, how firms are...

$30