Downtown Chestertown Association Reboots its Summer Sidewalk Sale


The Chestertown Sidewalk Sale, July 27-28, is two fun-filled days of amazing shopping deals in stores along Cannon St., Cross St., High St., and Park Row. Occupying the same weekend as Crazy Days, the newly redesigned event will feature evening shopping hours, wine and spirits tastings, additional food offerings and live music. “Our goal is to create a more vibrant event offering new experiences,” commented Downtown Chestertown Association President Jennifer Laucik Baker. “We hope to bring more people into the community and introduce them to some of our new, unique businesses.” What remains unchanged is the special pricing on the latest trends in clothing, home décor, gifts, books, music, and handcrafted items made by Kent County artisans and furniture makers.

The weekend kicks off on Friday, July 27, with stores opening and sales beginning at 10am. You’ll find brands you won’t find in big box stores, and many items discounted by an average of 40%. From 5-9 p.m., enjoy “Chestertown After Dark.” Shops will keep their doors open until 9pm where visitors will find bargains on a wide variety of merchandise while enjoying a festive downtown filled with food, music, and fun. When you’ve shopped up an appetite, visit Figg’s Ordinary, Bad Alfred’s, The Kitchen, Chester River Wine & Cheese Co., Play It Again Sam’s, or the Fish Whistle. For a quick bite on the go visit Park Row for Walker Family Deep Fried Baskets, Suzie Bee Hand Pies, and Lockbriar & Daughter Ice Cream.

Friday night the Downtown Chestertown Association is excited to welcome Maryland wine, beer and spirits producers from Kent, Talbot, and Cecil county. In addition to Chestertown’s own Bad Alfred’s Distilling, producers will offer tastings, as well as bottles for purchase to take home. Look for Crow Vineyard & Winery, Broken Spoke Vineyard & Winery, St. Michaels Winery, Lyon Distilling, and Bull & Goat Brewery in various locations around town from 5-9 p.m.

– Bull & Goat is on tap at Bad Alfred’s Distilling
– Broken Spoke Vineyards at The Finishing Touch
– Crow Winery between The Village House and Welcome Home
– Lyon Distilling at Chester River Wine & Cheese Co.
– St. Michael’s Winery at Gabriel’s of Chestertown
– Wine tasting at Chestertown Natural Foods

As you shop, sip, nosh, and stroll, we’ve planned an evening filled with live music and entertainment. Figg’s Ordinary is hosting free corn hole games in their Cross Street parking lot from 6-8pm. Entertainment and live performances include:

5:00 – 6:30: Pres Harding with lap steel in front of Bad Alfred’s Distilling
5:00 – 6:00: Fredy Granillo with acoustic guitar on corner of Cross & Cannon
6:00 – 7:30: Van Williamson jazz at Figg’s Ordinary and Gabriel’s of Chestertown
6:30 – 7:30: Jigs & Reels celtic at Bee Crafty and Barn Life Primitives

The family fun in our historic arts & entertainment district continues Saturday, July 28 with special sales, face painting, and hand dipped ice cream. Visit the farmer’s market early and come back for a day of shopping with us.

For a full lineup of events and a preview of specials, visit

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