Midnight Madness Comes to Town Next Monday

Many Winchester Center shops will offer extended hours, special sales, refreshments and more on the Monday after Thanksgiving.

Midnight Madness is coming to Winchester Center next Monday, Nov. 28. Many downtown stores will offer extended hours, special sales, music, refreshments and more.

“It’s fun – a lot of fun,” said Lori Schaefer, owner of .

This will be her shop’s second year of Midnight Madness and, after promoting the event more this year, she expects even more customers than last time.

The has arranged for the Jubilation Singers to entertain on the street corner by . Chip & Dale will be bring their bluegrass tunes to , and students will appear at , Pairings Food and Wine and other shops.

“We downtown shops, restaurants and service businesses are solicited every week throughout the year to support many local events and fundraisers,” said Judy Manzo, owner of Book Ends and president of the Winchester Chamber of Commerce. “This entertaining evening gives folks a great opportunity to shop local and keep some holiday dollars right here in Winchester.”

Pairings Food and Wine will be offering sparkling wine tastings paired with food, as well as 20 percent off wine, food and gift items in the store. There will also be a gift basket promotion of $10 off a basket of $50-$100 and $20 off a gift basket priced over $100. Get to Pairings Food and Wine before 10 p.m. though, as their liquor license requires they stop pouring at that time.

In addition to events at their store, Pairings Food and Wine will be traveling down the road to Flower Drum Boutique and during the Midnight Madness event. At Flower Drum Boutique, they will offer tastings of sparkling wines paired with food, and at Mad About Shoe there will be red and white wine tastings paired with cheese, charcuterie and cookies.

At , the celebration starts at 3 p.m. and runs until 6 p.m. in what owner Eric Keough calls “Afternoon Madness.” Santa will visit the store during those hours, and customers are invited to have their children sit on Santa’s lap and take pictures. Each child who sits on Santa’s lap will receive a small toy.

Employees will be dressed as elves, and classic children’s holiday movies will be playing. In addition, Keough will raffle off a pair of shoes every hour starting at 4 p.m. and announce the winners via megaphone to the entire center. 

“Kids Footstop is as excited for this event as kids are on Christmas morning!” Keough wrote in an email last week.

Other participating Midnight Madness merchants are: , , , , , , , , , Sells & Co., and . Check with individual stores for specific extended hours.


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