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Ongoing

The Red Ticket Raffle 2022!

Winchester Center Winchester

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

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

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

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

Winchester Center Winchester

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...