Bad Alfred’s
Located in historic downtown Chestertown, Maryland, Bad Alfred’s is a brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas.
(443) 282-0163
Business Tags
323 High St.
Chestertown, MD 21620
Days Open
Thurs, Fri, Sat
Hours
Thursday & Friday, 5 - 8 pm, Saturday noon - 8 pm
DCA Member
Brampton Inn Bed and Breakfast
A quiet Bed and Breakfast less than a mile from Chestertown, Maryland.
410-778-1860
25227 Chestertown Road
Chestertown, Maryland 21620
Days Open
All
DCA Member
Casa Carmen
Serving wine and tapas, our tasting room is created in the spirit of the traditional wine bodegas of Spain and South America—an unpretentious place to drink well, eat well, and enjoy good company.
443-203-8023
312 Cannon Street
Chestertown, MD 21620
Days Open
Wed, Thurs, Fri, Sat
Hours
Wednesday through Saturday, 4 pm to 9 pm
DCA Member
Chesapeake Bank & Trust Company
410-778-1600
245 High Street
Chestertown
Days Open
Mon, Tues, Wed, Thurs, Fri
Hours
9 am - 5 pm
DCA Member
Chester River Packet
A 2 Hour Cruise on the Chester River
410 635 0321
Chestertown. MD 21820
Days Open
All
Hours
Varies
DCA Member
Chester River Wine & Cheese Co.
Chester River Wine & Cheese Co. is a specialty food market offering international and domestic wine, cut-to-order cheese, onsite wine by the glass, and cheese board service.
443-282-0220
117 South Cross Street
Chestertown, Maryland 21620
Days Open
All
Hours
Tues-Sat 10am-7pm; Sun & Mon 10am-4pm
DCA Member
Chestertown Natural Foods
Chestertown Natural Foods features local, all-natural and organic vendors and strives to provide the best gourmet products available. We are a full service grocery in downtown Chestertown, independently owned and operated by Certified Nutritional Consultant (C.N.C.) Trish Young-Gruber.
410-778-1677
Business Fax
410-778-6537
303 Cannon St
Chestertown, MD 21620
Days Open
All
Hours
Mon: 12-6, Tue: 12 - 8, Wednesday & Thursday 10-7, Fri: 12-8, Sat: 9-8, Sun: 10-7
DCA Member
Diane Rappisi Fine Art
A vibrant working art studio, teaching space and gallery, offering a wide variety of products and services including original fine art, commissioned portraits, art instruction and private critiques, as well as traveling workshops.
609-206-1907
241B High Street
Chestertown, Md 21620
Hours
By Appointment until further notice. Please Call
DCA Member
Evergrain Bread Company
Evergrain’s core mission is “retro-innovation;” to combine the best of traditional baking theory with the best new technology and ingredients. We also believe in time—an essential element of baking is patience. We give our breads and pastries the time they need to let fermentation work its alchemy, developing flavors to their greatest possible deliciousness.
410-778-3333
201-203 High Street
Chestertown
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed– Sat 7:00 AM – 5:00 PM , Closed Monday & Tuesday
DCA Member
Figg’s Ordinary

Logo or image
Figg’s Ordinary is a gluten and refined-sugar free café and bakery located in historic downtown Chestertown on Maryland’s Eastern Shore. We serve an entirely vegetarian menu of freshly-made salads, sandwiches, breakfast, smoothie bowls, baked goods, snacks, and more, all made with organic, locally-grown, seasonal produce.

In colonial days, ‘ordinaries’ served as gathering places for townspeople, which is exactly what we aim to be (with some essential modern upgrades, of course).

So come, gather, eat, share, and learn with us here at Figg’s!
443-282-0061
207 S Cross St. #102
Chestertown, MD 21620
Days Open
Tues, Wed, Thurs, Fri, Sat
Hours
Tuesday -through Saturday, 8 am - 2 pm
DCA Member
Great Oak Manor
Escape to Great Oak Manor!

There is a special place just waiting for you on the Chesapeake Bay on Maryland’s Eastern Shore. Our Chestertown, Maryland bed and breakfast is a magnificent country estate built in the Georgian Style. It is a charming B&B with twelve guest rooms and a fabulous family style accommodation in addition to spacious common areas.
800-504-3098
10568 Cliff Road
Chestertown, Maryland 21620
Days Open
All
DCA Member
Hegland Glass
Each piece of our art glass reveals our captivation with the creativity of the design process, the technical challenge of construction, and the precision of coldworking.  Our open designs reflect the rural horizons and lively waterways that surround us, resulting in works that flow across edge boundaries into the world beyond.
410-870-5432
315 High Street, Suite 103
Chestertown
Days Open
Fri, Sat
Hours
Fridays 11am to 3pm, Saturdays 10am to 3pm or, by appointment
DCA Member
Houston’s Dockside Emporium
The place to shop on the Eastern Shore for CLASSIC APPAREL FOR WOMEN AND MEN
@houstonsdocksideemporium
410-778-9079
315 High Street Suite 101
Chestertown MD 21620
Days Open
All
Hours
Monday - Saturday 9:30 am - 5:30 pm, Sunday 11 am - 4 pm
DCA Member
410-778-3636
408 High Street
Chestertown MD 21620
DCA Member
MassoniArt
Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years.
410-778-7330
203 High Street, 2nd Floor
Chestertown
Hours
As the COVID-19 (coronavirus) continues to permeate every aspect of our lives, we recognize the need to take preventative measures in order to ensure the safety of our staff, our artists, and our patrons. While the gallery remains closed, we will offer online versions of our exhibitions whenever possible. For inquiries please contact Carla Massoni – 410-778-7330, text 410-708-4512, or info@massoniart.com.
DCA Member
Mimi’s Closet
Mimi's is the boutique with lots of variety. Our staff can help you put a look together for any occasion or you can browse through our great selection of casual or dressy choices. Stop in and say hello. . . We think you'll enjoy the "Mimi's Difference"!
443-282-0225
307 High Street
Chestertown MD 21620
Days Open
All
Hours
Mon - Sat 10 am - 5 pm, Sun 11 am - 4 pm
DCA Member
Music Life
Instrument lessons, sales and repair. Students of all ages and any skill level can discover the delight of music and experience the joy of sharing it with others
410-778-7010
241 High Street
Chestertown
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon 3-6, Tues-Thurs 10:30-6:30, Fri 10:30-7, Sat 9:30-5
DCA Member
Riverside Unique
Unique handmade gifts made from local Maryland Artisans.
410-778-2073
Business Fax
410-778-2074
227 High Street
Chestertown, MD 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon- Fri: 10am - 5pm. Sat 10 am - 2pm
DCA Member
Robert Ortiz Studios

Logo or image
This is a full time woodworking studio. Robert Ortiz designs and makes contemporary furniture, a fusion of modern, Arts & Crafts, Shaker and Asian influences.
410-810-1400
207 So. Cross Street,
Chestertown, MD 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Monday through Friday, 8:30 - 5;30 (Closed for lunch noon -1:30)
410-778-5954
105 S. Cross Street
Chestertown MD 21620
DCA Member
The Artists’ Gallery
Six local artists presenting fine art along with the areas best crafts, plus monthly exhibits featuring other local artists
410.778.2425
239 High Street
Chestertown MD 21620
Days Open
Sun, Tues, Wed, Thurs, Fri, Sat
Hours
Tues - Sat 10 - 5, Sun 12:30 - 4:30
DCA Member
The Bookplate
The Bookplate is an independent bookstore in the heart of downtown Chestertown, MD. We specialize in first editions, regional history, and fiction, but our collection has gradually expanded to include art books, field guides, essays, comics, and beyond. Plus custom, hand painted pottery imported from Portugal and Spain.
410-778-4167
112 S. Cross Street
Chestertown
Days Open
All
Hours
M - S -10:00 - 5:00, Sun. - 11:00 - 3:00
DCA Member
410-648-2309
Chestertown MD 21620
DCA Member
The Kitchen at the Imperial Hotel
Award winning Casual Fine Dining. Voted Best Crab Cake 2017/2018 What's Up Mag and 2012/2013/2014 Chesapeake Bay Mag. Best Chef on Easter Shore 2013/2014/2015 What's Up Mag.
410-778-5000
208 High Street
Chestertown MD 21620
Days Open
All
Hours
Monday - Saturday, 11:30 am - 9 pm, Sunday Brunch 10 am - 3 pm, DInner 5 pm - 9 pm
DCA Member
410-778-3500
100 Spring Avenue
Chestertown, Maryland 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
DCA Member
Tish Fine Art Plus
Tish Fine Art Plus is an art gallery featuring local artists alongside national and international creatives.  In addition, we carry a line of custom clothing, jewelry and furniture by local crafts persons with an emphasis on  sustainable,  quirky and unique.  Tish also features live music on monthly First Friday and select Saturdays.

@tishfaplus
410 282 7551
343 High Street
Chestertown, MD 21620
Days Open
Sun, Thurs, Fri, Sat
Hours
Thurs/Fri noon to 5 pm, Sat. 9 am - 1:30 pm & 3:30 - 6 pm, Sunday noon - 1 pm
DCA Member
Twigs & Teacups
Twigs & Teacups is a store dedicated to the art of gift giving. We have an eclectic assortment of items for any occasion! Our assortment of kitchenware, clothing, books, toys, and odds and ends ranges from old school to quirky, and from classic to modern.
410-778-1708
111 S. Cross Street
Chestertown
Days Open
All
Hours
Mon-Sat: 10-5, Sunday: 12-4
DCA Member
Walnut & Wool
Clothing.  Furniture.  Home Decor

Instagram
(410) 778-9000
321 High Street
Chestertown, MD 21620
Days Open
Sun, Mon, Wed, Thurs, Fri, Sat
Hours
Sunday & Monday Noon - 5 pm, Wednesday & Thursday Noon - 6 pm, Friday Noon - 7 pm, Saturday 10 am - 7 pm,
410-778-7201
300 Washington Avenue
Chestertown
DCA Member
Angela’s Cottage
Local Artisan Gift Shop. Where creativity meets wellness.
Hand made pottery, jewelry, essential oils
Open First Fridays until 7pm

Service Hours. By Appointment Only
Monday- Thursday 5:30pm - 8pm
Friday & Saturday 8am - 8 pm
Sunday noon - 5 pm
443 282 0027
335 High Street
Chestertown, MD 21620
Days Open
Fri, Sat
Hours
10 am - 5 pm
DCA Member
Bee Crafty Collectibles
Upcycled vintage furniture, home decor, custom wooden signs, gift shop
410 778 0479
Business Tags
335 High Street
Chestertown, MD 21620
DCA Member
Bohemia Trading Company
301 968 5778
7400 Church Hill Rd
Chestertown, MD 21620
Hours
Thurs/Fri/Sat 11 - 5, Sun 12 - 5
DCA Member

Logo or image
Colloquium: from the Latin root COL = together and LOUGUI = to talk. To come together to talk about important issues.

Cat Colloquium is a warm, friendly, inquisitive place for community to come together in the company of cats.
410 778 6369
Business Tags
215 High St
Chestertown, MD 21620
Days Open
Sun, Mon, Wed, Thurs, Fri, Sat
Hours
Wed to Sat 11 - 4, Sun, on 1 -2
DCA Member
Chester River Soaperie
443 867 8356
Business Tags
222 Devon Drive
Chestertown, MD 21620
Days Open
All
Hours
website always open. Chestertown Farmers' Market Saturdays 8 am - noon
DCA Member
Chestertown RiverArts
Community Arts Center: art gallery, gift shop featuring local artists, KidSPOT, Clay Studio, classes and workshops
310 778 6300
315 High Street, Suite 106 (Breezeway)
Chestertown, MD 21620
Days Open
Sun, Thurs, Fri, Sat
Hours
Thurs & Fri 11 - 3, Sat 10 - 4, Sun 11 - 2
DCA Member
Coco’s Pet Center
Everything you need to keep their tail wagging.
410 282 0013
Business Tags
335 High Street, B
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed 11 -4, Thurs 10 - 4Fri 10 - 5, Sat 9 - 5
Cross Street Realtors
A boutique real estate shop owned by local Realtors with diverse areas of expertise including, but not limited to Farms, Waterfront Real Estate, Hunting Properties, Residential, Historic Estates, Commercial Sales, and Equine Facilities.
410 778 3779
201 S Cross Street
Chestertown, MD 2160
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
DCA Member
Les Poissons Gallery
Fine Art.
310 708 0017
210 S Cross St. #104
Chestertown, MD 21610
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed - Fri 11 - 5, Sat 10 - 5, Sun noon - 4
Lewes Liquors
A Full Service package store.  
Beer, Wine, Spirits and more!
Conveniently located on upper High Street
410 778 1356
840 High Street
Chestertown, MD 21620
Days Open
All
Hours
7am - 10 pm Mon - Wed/7 am - 11pm Thurs & Fri/8 am - 11pm Sat/8 am - 10pm Sunn
DCA Member
Modern Stone Age Kitchen
410 996 4776
Business Tags
236 Cannon St.
Chestertown, MD 21620
Days Open
Wed, Thurs, Fri, Sat
Hours
Wed/Thurs/Fri 10 - 4/Sat 8 - 1
DCA Member
Sarah Paige Studio Salon
Distinction in Hair Color and Design.
We are a Mother/Daughter Team. Talented stylists with years of dedication in the beauty industry.
Experience is our legacy of mentors and advanced education. This is the key to our success and you are our amazing guests and we appreciate each and every one of you.

443 282 0092
312 Cannon St., Suite 3 (GreenCottage)
Chestertown, MD 21620
Days Open
Tues, Wed, Thurs, Fri, Sat
Hours
Tues 9 -3, Wed & Thurs 9 - 7, Fri 9 - 5, Sat 9 - 3
DCA Member
Teknika
Residential kitchens, baths and custom cabinetry.
Open By Appointment
410 778 2036
Business Tags
335 High St., Unit C
Chestertown, MD 21620
DCA Member
The Finishing Touch
Located in the heart of Chestertown, MD, we specialize in custom framing, fine art, select gifts, artist’s materials, digital imaging and art reproduction.
410 778 5292
311 High Street
Chestertown, MD 21620
Days Open
All
Hours
Mon - Thurs 9:30 - 5:30, Fri & Sat 9:30 - 7, Sun 11 - 3
DCA Member
The Spicerie
443 867 8356
222 Devon Drive
Chestertown, MD 21620
Days Open
All
Hours
website always open. Chestertown Farmers' Market Saturdays 8 am - noon
DCA Member
Tiny Tots Boutique
Tiny Tots Boutique is a locally owned and operated clothing business that offers a large selection of well-made kids' wear. Once you shop with us, you'll keep coming for more. We carry fashion-forward clothes for boys and girls. All of our merchandise is high quality. You also don't have to worry about high boutique prices, as we have priced our clothing products affordably.
443 282 0100
Business Tags
114 A S Cross Street
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed 11 -3, Thurs 11 - 4, Fri 11 - 5, t 10 - 4, Sun noon - 3
DCA Member
Zelda’s Speakeasy
Open when the green light is on! Serving monthly Alfresco DInners in warm weather.
Occasional Live Music. Check FB page for more info
Business Tags
108 S Cross Street, 2nd Floor
Chestertown, MD 21620
DCA Member