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June 2, 2025

Chestertown Spy

Nonpartisan and Education-based News for Chestertown

5 News Notes

DCA Introduces Chestertown Cash

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The Downtown Chestertown Association is offering Chestertown Cash for the holiday season in coordination with the State of Maryland’s Shop Maryland for the Holidays program and the national Shop Small effort.  The certificates are redeemable at the more than 30 participating shops and businesses in Downtown and Greater Chestertown displaying the Chestertown Cash Welcome Here sign.

The local premium: For every $100 spent at your local independent business, $68 remains in the community, vs. $48 for chain stores and $0 when shopping online. Local shop owners employ your neighbor, buy goods locally, and support local charitable organizations. These added dollars circulate in the local economy and translate into more jobs and economic activity.

Chestertown Cash certificates are available at The Finishing Touch, 311 High Street in Chestertown  410-778-5292, and online at https://www.downtownchestertown.org/. For more information, email [email protected].

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Holiday Season Kicks Off with Ladies’ Night November 12

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Head out for an evening of fun in Chestertown this Thursday for the annual Ladies Night, sponsored by the Downtown Chestertown Association.  Shops and eateries will be open late with deals and specials for all – particularly the ladies.

The theme is Shop Safe and Shop Local. Shops are all focused on creating a safe and enjoyable experience so you can get a head start on your holiday lists before the Thanksgiving rush. Participating shops include Bee Crafty, Bookplate, Coco’s, Houston’s Dockside Emporium, Mimi’s Closet, Riverside Unique, The Finishing Touch, Twigs & Teacups, Walnut & Wool, and Welcome Home.

Do not forget to stop in for a bite to eat and cheer! Bad Alfred’s Distilling, Casa Carmen, The Kitchen, Zelda’s and 98 Cannon are all offering Ladies Night specials.

Mark your calendars for another festive local shopping day-Small Business Saturday, November 28, and the arrival of Santa!

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Scarecrows and Carved Pumpkins to Decorate Downtown Chestertown

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The Downtown Chestertown Association and the Chestertown Arts & Entertainment District are joining forces to sponsor two decorating contests that will bring Halloween spirit to downtown sidewalks — one for parking meter scarecrows and the other for carved pumpkins.

The Scarecrow competition revives a tradition started during the tenure of Mayor Margo Bailey.  Entrants will be assigned a specific parking meter to decorate with their scarecrow anytime from Sunday, October 25 through Tuesday, October 27. No political messaging will be allowed.

The Mayor and Council will act as judges, and their top three choices will each receive a $100 cash prize. The Scarecrows will stay up through Sunday, November 7 as conditions allow.

The scarecrow decorating activity is open to everyone: businesses, organizations and individuals. For more information and to register for the contest, contact [email protected] or call 443-480-1987.

Artful pumpkins and Jack-o-Lanterns! 

The carved pumpkin contest is open to families, friend groups and individuals (no businesses). To enter, bring your carved pumpkin(s) to The Finishing Touch, 311 High Street, on Thursday, October 29 between the hours of 9:30 a.m. and 5:30 p.m. and make sure to include a completed entry form.  Request an entry form by email at [email protected] or fill one  out at The Finishing Touch. All the pumpkin entries will be displayed on downtown sidewalks Friday and Saturday evenings, October 30 and 31, between 5:00 and 10:00 p.m.

Cash prizes of $50, $40, and $30 will be awarded for 1st, 2nd and 3rd place winners in four categories: Scariest, Funniest, Most Creative, and Best Artistry.  Members of the Arts & Entertainment District Advisory Board will serve as judges.

The list of winners of both contests will be posted in the window at The Finishing Touch at 1:00 p.m. Saturday and announced through social media channels.

Start designing that scarecrow and/or pumpkin and make plans to come downtown Friday or Saturday evening of Halloween weekend to enjoy the creations conjured up by other community members. Costumes encouraged!

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Crazy Days Ahead! July 23 Through July 25

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Mark your calendars for Chestertown’s annual sidewalk sale, Crazy Days. The shopping begins on Thursday, July 23 and runs through Saturday, July 25, with many stores carrying the specials into Sunday. This mid summer tradition is sponsored by the Downtown Chestertown Association, (DCA).

Shop safely outside! Great deals can be found on everything from men’s and women’s designer fashions, children’s clothing and toys, jewelry, home décor, painting, crafts, kitchen items, books, art supplies, pampered pet must- haves and even musical instruments. Shops will be open Friday and Saturday night until 7 pm, and the Kitchen at the Imperial will be hosting one of its popular al Fresco dinners on Saturday. Reservations highly suggested.

Restaurants are posting “crazy days” specials, the Animal Care Shelter for Kent County will offer hot dog lunches from 11 am to 4 pm all three days, and the DCA will be handing out free popcorn.Ice Cream? Stam’s is now open until 8 pm on Friday and Saturday.

Shoppers and browsers, please practice corona courtesies; wear a mask and respect social distancing – 6 feet when possible. We want all of our customers and employees to stay safe!

Your Chestertown independent businesses look forward to seeing you.

Don’t miss the latest! You can subscribe to The Chestertown Spy‘s free Daily Intelligence Report here

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Downtown Chestertown Celebrates Independence Day Weekend

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Chestertown is providing a festive start to your holiday weekend with extended hours for evening browsing in your favorite downtown shops and outside dining this Friday, July 3.

Got a pampered pooch? Don’t miss the town’s newest addition, Coco’s, at 335 High Street.Just up the street, Tish Fine Art Plus will be featuring live music. And psst, Zelda’s on Cross Street should be opening up at 5pm, serving frozen concoctions.  Look for the green light.

The popular “Chestertown al Fresco Dining” moves to Casa Carmen on Friday. The wine bar is located at 312 Cannon Street. 443 203 8023.  Reservations are strongly encouraged; tapas, small plates and paella.

Don’t forget to mark your calendars for Crazy Days, downtown Chestertown’s annual midsummer sidewalk sale, July 23 through 25. Safe shopping outside – plan ahead and come early for best selections!

Don’t miss the latest! You can subscribe to The Chestertown Spy‘s free Daily Intelligence Report here

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Music in Your Ears in Downtown Chestertown

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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 [email protected].

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Mastering the Art of Gingerbread Cookie Decorating

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Calling all budding pastry chefs! Sign up now for the Downtown Chestertown Association’s  Annual Gingerbread Cookie Workshop. This FREE event will be Saturday, December 7, 2:30 pm. at KidSPOT for children ages 4 – 12.

Pre-registration is required as space is limited.

Email [email protected] for more information and to register.

Chef Stu Cawley, assisted by various eleves,will demonstrate the proper icing technique with gingerbread cookies generously donated by Little Village Bakery.

This annual event is not possible without our sponsors: Twigs and Teacups, and Little Village Bakery. It is presented by the Downtown Chestertown Association and hosted by RiverArts’ KidSPOT. Special thanks to Stu Cawley and elves.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Crazy Days Ahead! July 25 Through July 27

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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.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Blue Grass, BBQ, and More at Downtown Chestertown Block Party

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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 ([email protected]) or Kay MacIntosh ([email protected]), or visit the Main Street Chestertown Facebook page and click on Events.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

September First Friday Celebrates Chestertown United

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Chestertown LIVES UNITED. The First Friday of every month participating Downtown Chestertown Association (DCA) members open their doors and invite the community to step inside for an evening of food, music, art, and shopping. During First Friday we celebrate our community and thank customers for shopping local and shopping small.

Please join us Friday, September 7 from 5:00 – 8:00 p.m. as the DCA unites with The United Way of Kent County, Washington College, and the 26 local United Way Agencies who make our community a great place to live.

We’ve planned an evening filled with fun. Stroll High Street to meet local non-profit organizations who will share their vision and goals for an even greater Kent County. Visit the United Way booth outside of Chesapeake Bank and Trust to learn more about their annual giving campaign. Meet Kurt Landgraf, President of Washington College, at The Hynson-Ringgold House from 5:00 – 6:30 p.m. Slip inside our small independently-owned shops for the latest fall merchandise and fantastic sales on late-summer merchandise. Visit Chestertown RiverArts for the Abstract and Ceramics Show and Massoni Art Gallery for a celebration of work by artist Ken Schiano.

We’re excited to host Washington College student musicians Conor Maloney (5:15 at Gabriel’s Of Chestertown) Madison Morton (6:15 at CREATE), and Emma Hoey (7:15 at Blackbird Boutique). Check out local favorite, Dovetail, on the steps of Chesapeake Bank and Trust. As you stroll Park Row, High St., Cross St., and Cannon St., look for giveaways, snacks, cold drinks, sales, games, and more.

Fountain Park will be transformed into a fun-zone with free corn-hole and activities for all. At 8:00 p.m. the Chestertown Recreation Commission will host a free screening of Beauty and the Beast. In addition to our downtown restaurants, enjoy food by the Walker Family Fried Food Truck, Suzie Bee Hand pies, and Lockbriar Ice Cream along Park Row.

The 26 participating United Way Agencies include: American Red Cross of the Delmarva Peninsula, Big Brothers/Big Sisters of the Eastern Shore, Del-Mar-Va-Council BSA, Camp Fairlee/Easter Seals, Character Counts! Kent County, Community Food Pantry, Community Mediation Upper Shore, Compass Regional Hospice, Echo Hill Outdoor School, Fiddlesticks! Youth Orchestra, For All Seasons, Girl Scouts of the Chesapeake Council, Good Neighbor Fund/ CVMA, Horizons of Kent & Queen Anne’s, Kent Association of Therapeutic Riding, Kent County CARES Foundation, Kent County Medical Day Care Fdn., Kent Forward, KidSPOT, Mid-Shore Council on Family Violence, Playmakers Camp (@GCA), Rebuilding Together, RHYC Sailing School Scholarship Program, Saint Martin’s Ministries, Samaritan Group, United Needs and Abilities.

For more information about First Friday, please contact Jennifer Laucik-Baker of the Downtown Chestertown Association at [email protected], or visit www.facebook.com/downtownchestertown for a full lineup of events.

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.