Bad Alfred’s
Address: 323 High St.
Chestertown, MD 21620
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: ,
Days Open: Thurs, Fri, Sat
Hours: Thursday & Friday, 5 - 8 pm, Saturday noon - 8 pm
DCA Member
Brampton Inn Bed and Breakfast
Address: 25227 Chestertown Road
Chestertown, Maryland 21620
A quiet Bed and Breakfast less than a mile from Chestertown, Maryland.
410-778-1860
Days Open: All
DCA Member
Casa Carmen
Address: 312 Cannon Street
Chestertown, MD 21620
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
Days Open: Wed, Thurs, Fri, Sat
Hours: Wednesday through Saturday, 4 pm to 9 pm
DCA Member
Chesapeake Bank & Trust Company
Address: 245 High Street
Chestertown
410-778-1600
Days Open: Mon, Tues, Wed, Thurs, Fri
Hours: 9 am - 5 pm
DCA Member
Chester River Packet
Address: Chestertown. MD 21820
A 2 Hour Cruise on the Chester River
410 635 0321
Days Open: All
Hours: Varies
DCA Member
Chester River Wine & Cheese Co.
Address: 117 South Cross Street
Chestertown, Maryland 21620

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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
Days Open: All
Hours: Tues-Sat 10am-7pm; Sun & Mon 10am-4pm
DCA Member
Chestertown Natural Foods
Address: 303 Cannon St
Chestertown, MD 21620
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
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
Address: 241B High Street
Chestertown, Md 21620
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
Hours: By Appointment until further notice. Please Call
DCA Member
Address: 121 Flatland Road
Chestertown MD 21620

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410-778-6133
DCA Member
Evergrain Bread Company
Address: 201-203 High Street
Chestertown
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
Days Open: Sun, Wed, Thurs, Fri, Sat
Hours: Wed– Sat 7:00 AM – 5:00 PM , Closed Monday & Tuesday
DCA Member
Figg’s Ordinary
Address: 207 S Cross St. #102
Chestertown, MD 21620

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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
Days Open: Tues, Wed, Thurs, Fri, Sat
Hours: Tuesday -through Saturday, 8 am - 2 pm
DCA Member
Great Oak Manor
Address: 10568 Cliff Road
Chestertown, Maryland 21620
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
Days Open: All
DCA Member
Hegland Glass
Address: 315 High Street, Suite 103
Chestertown
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
Days Open: Fri, Sat
Hours: Fridays 11am to 3pm, Saturdays 10am to 3pm or, by appointment
DCA Member
Houston’s Dockside Emporium
Address: 315 High Street Suite 101
Chestertown MD 21620
The place to shop on the Eastern Shore for CLASSIC APPAREL FOR WOMEN AND MEN
@houstonsdocksideemporium
410-778-9079
Days Open: All
Hours: Monday - Saturday 9:30 am - 5:30 pm, Sunday 11 am - 4 pm
DCA Member
Address: 408 High Street
Chestertown MD 21620
410-778-3636
DCA Member
MassoniArt
Address: 203 High Street, 2nd Floor
Chestertown
Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years.
410-778-7330
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
Address: 307 High Street
Chestertown MD 21620
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
Days Open: All
Hours: Mon - Sat 10 am - 5 pm, Sun 11 am - 4 pm
DCA Member
Music Life
Address: 241 High Street
Chestertown
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
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
Address: 227 High Street
Chestertown, MD 21620
Unique handmade gifts made from local Maryland Artisans.
410-778-2073
Business Fax: 410-778-2074
Days Open: Mon, Tues, Wed, Thurs, Fri, Sat
Hours: Mon- Fri: 10am - 5pm. Sat 10 am - 2pm
DCA Member
Robert Ortiz Studios
Address: 207 So. Cross Street,
Chestertown, MD 21620

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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
Days Open: Mon, Tues, Wed, Thurs, Fri, Sat
Hours: Monday through Friday, 8:30 - 5;30 (Closed for lunch noon -1:30)
Address: 105 S. Cross Street
Chestertown MD 21620
410-778-5954
DCA Member
Address: 239 High Street
Chestertown MD 21620
410.778.2425
DCA Member
The Bookplate
Address: 112 S. Cross Street
Chestertown
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
Days Open: All
Hours: M - S -10:00 - 5:00, Sun. - 11:00 - 3:00
DCA Member
Address: Chestertown MD 21620
410-648-2309
DCA Member
Address: 101 Church Alley
Chestertown MD 21620
410-778-3499
DCA Member
The Kitchen at the Imperial Hotel
Address: 208 High Street
Chestertown MD 21620
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
Days Open: All
Hours: Monday - Saturday, 11:30 am - 9 pm, Sunday Brunch 10 am - 3 pm, DInner 5 pm - 9 pm
DCA Member
Address: 100 Spring Avenue
Chestertown, Maryland 21620
410-778-3500
Days Open: Mon, Tues, Wed, Thurs, Fri, Sat
DCA Member
Tish Fine Art Plus
Address: 343 High Street
Chestertown, MD 21620
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
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
Address: 111 S. Cross Street
Chestertown

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410-778-1708
Days Open: All
Hours: Mon-Sat: 10-5, Sunday: 12-4
DCA Member
Walnut & Wool
Address: 321 High Street
Chestertown, MD 21620
Clothing.  Furniture.  Home Decor

Plus... Gus and Tallulah!

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(410) 778-9000
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,
DCA Member
Address: 300 Washington Avenue
Chestertown
410-778-7201
DCA Member