Shoppers and visitors in downtown Chestertown over the Thanksgiving holiday may have been humming along to music as they shopped, dined, strolled around town and perused the Farmers’ Market.

Thanks to generous support from Chesapeake Bank and Trust, the Downtown Chestertown Association has installed two outdoor speakers that are capable of playing seasonally appropriate music year round as well as making announcements. This project has been a topic of discussion for years at DCA meetings, and we are thrilled that it has finally come to fruition. Special thanks goes to WCTR’s Brian Moore and Leslie Sea for technical support and musical arrangements, The Historical Society of Kent County for use of their building, and Bob Ramsey of the Finishing Touch for installing the system.

It is our hope to add additional speakers in the coming year to expand the reach down both Cross and High Streets to encompass the whole downtown. If you are interested in assisting with expansion, please email downtownchestertown@gmail.com.

Downtown Chestertown’s annual shopping bonanza, Crazy Days, is right around the corner. The sidewalk sale begins on Thursday, July 25 and runs through Saturday, July 27, with many stores carrying the specials into Sunday.  This mid summer tradition is sponsored by the Downtown Chestertown Association.

Great deals can be found on everything from men’s and women’s designer fashions, children’s clothing and toys, jewelry, home décor, kitchen must-haves, wine and cheese, books, art supplies, and even musical instruments.  There is plenty for the younger ones:  free face painting Thursday 10 am to noon, Friday 10 am – 1pm and Saturday 11 am to 2 pm.  Kent County Parks and Rec will be offering games in Fountain Park during the day on Friday.  The Lockbriar Ice Cream Cart will be in town Friday and Saturday.

Shops will be open Friday night until 7 pm. For those who wish to grab something to eat while perusing the bargains, downtown restaurants will be offering “Crazy” food and drink specials. Oyster lovers – Scott Budden of Oyster Point Farms will be in town Friday from 5 -7 pm with his ‘buck a shuck.“ Check out the Downtown Chestertown Facebook page for more deals https://www.facebook.com/pg/downtownchestertown/events/

Bring the whole family to Downtown Chestertown for a fun filled day – or weekend!

The parking is always free.

Main Street Chestertown and the Downtown Chestertown Association (DCA) will host a Fall Harvest Block Party on Saturday, September 15, from noon to 4 p.m. in the 100 block of S. Cross Street.  The Baltimore-based bluegrass band Dirty Grass Players and Chestertown’s own Jigs & Reels will provide the live music for the afternoon event, which will offer plenty of food and beverage, family activities and shopping.

Event committee chair Sean Downey, owner of Barn Life Primitives and Architectural, says the  block of Cross Street between High and Cannon Streets will fill with vendors offering pit beef barbecue, hotdogs, oysters, shaved ice, ice cream, popcorn, kettle corn, sodas, beer and wine. Entertainment will include a children’s art activity hosted by Kaleidoscope Children’s Art Studio, Corn Hole Toss, Giant Connect Four, and an Irish dance performance.

The Dirty Grass Players put an improvisational spin on traditional bluegrass vocal harmonies. Band members are Alex Berman on banjo and vocals, Ben Kolakowski on guitar and vocals, Alex Tocco on fiddle and vocals, Ryan Rogers on mandolin, and Colin Rappa on bass fiddle.  Their sound is influenced by well-known traditional bluegrass players such as Flatt and Scruggs, and “newgrass” talents that include Tony Rice and the Infamous String Dusters.   It also veers into jazz-style improvisation and rock/R&B tributes to the Grateful Dead, James Brown and other music legends.

Keeping the party going between bluegrass sets will be Paul McDonald and John Gillespie of Jigs & Reels. The duo plays Irish dance music, along with some Scottish tunes, on the fiddle, concertina and penny whistle. Their music will accompany a dance demonstration by students from the Hester Academy of Irish Dance.

Main Street Chestertown and DCA invite everyone to come downtown for the Farmers Market (bring a cooler for your produce!) and then stay downtown to enjoy some great music, food, and fun.  For more information, contact Sean Downey (13beaterstreet@gmail.com) or Kay MacIntosh (kay.chestertown@gmail.com), or visit the Main Street Chestertown Facebook page and click on Events.

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 www.facebook.com/downtownchestertown.