- Art Gallery (5)
- Artists (5)
- Bakery (2)
- Bank (2)
- Bar with Food (4)
- Bath & Body Products (1)
- Education (4)
- Event Venue (5)
- Gourmet Food (3)
- Grocery (2)
- Live Music (1)
- Lodging (3)
- Media (1)
- Package Store (1)
- Pets (1)
- Realtor (1)
- Restaurant (8)
- Services (5)
- Shops (15)
- The Arts (2)
- Vineyards (1)
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
Chestertown, MD 21620
Days Open
Thurs, Fri, Sat
Hours
Thursday & Friday, 5 - 8 pm, Saturday noon - 8 pm
DCA Member
Upcycled vintage furniture, home decor, custom wooden signs, gift shop
410 778 0479
Business Tags
335 High Street
Chestertown, MD 21620
Chestertown, MD 21620
DCA Member
608 215 2501
207 S Cross Street
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed -Fri 10 - 5, Sat 9 - 4, Sun noon - 4
DCA Member
301 968 5778
7400 Church Hill Rd
Chestertown, MD 21620
Chestertown, MD 21620
Hours
Thurs/Fri/Sat 11 - 5, Sun 12 - 5
A quiet Bed and Breakfast less than a mile from Chestertown, Maryland.
410-778-1860
25227 Chestertown Road
Chestertown, Maryland 21620
Chestertown, Maryland 21620
Days Open
All
DCA Member
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
Chestertown, MD 21620
Days Open
Wed, Thurs, Fri, Sat
Hours
Wednesday through Saturday, 4 pm to 9 pm
DCA Member
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.
Cat Colloquium is a warm, friendly, inquisitive place for community to come together in the company of cats.
410 778 6369
215 High St
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Mon, Wed, Thurs, Fri, Sat
Hours
Wed to Sat 11 - 4, Sun, on 1 -2
DCA Member
410-778-1600
245 High Street
Chestertown
Chestertown
Days Open
Mon, Tues, Wed, Thurs, Fri
Hours
9 am - 5 pm
DCA Member
A 2 Hour Cruise on the Chester River
410 635 0321
Chestertown. MD 21820
Days Open
All
Hours
Varies
443 867 8356
Business Tags
222 Devon Drive
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
All
Hours
website always open. Chestertown Farmers' Market Saturdays 8 am - noon
DCA Member
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
Business Tags
117 South Cross Street
Chestertown, Maryland 21620
Chestertown, Maryland 21620
Days Open
All
Hours
Tues-Sat 10am-7pm; Sun & Mon 10am-4pm
DCA Member
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
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
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
Chestertown, MD 21620
Days Open
Sun, Thurs, Fri, Sat
Hours
Thurs & Fri 11 - 3, Sat 10 - 4, Sun 11 - 2
DCA Member
Everything you need to keep their tail wagging.
410 282 0013
335 High Street, B
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed 11 -4, Thurs 10 - 4Fri 10 - 5, Sat 9 - 5
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
Chestertown, MD 2160
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
DCA Member
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
Chestertown, Md 21620
Hours
By Appointment until further notice. Please Call
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
Chestertown
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed– Sat 7:00 AM – 5:00 PM , Closed Monday & Tuesday
DCA Member
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.
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
Chestertown, Maryland 21620
Days Open
All
DCA Member
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
Chestertown
Days Open
Fri, Sat
Hours
Fridays 11am to 3pm, Saturdays 10am to 3pm or, by appointment
DCA Member
The place to shop on the Eastern Shore for CLASSIC APPAREL FOR WOMEN AND MEN
@houstonsdocksideemporium
@houstonsdocksideemporium
410-778-9079
315 High Street Suite 101
Chestertown MD 21620
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
Chestertown MD 21620
DCA Member
Fine Art.
310 708 0017
210 S Cross St. #104
Chestertown, MD 21610
Chestertown, MD 21610
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Wed - Fri 11 - 5, Sat 10 - 5, Sun noon - 4
A Full Service package store.
Beer, Wine, Spirits and more!
Conveniently located on upper High Street
Beer, Wine, Spirits and more!
Conveniently located on upper High Street
410 778 1356
840 High Street
Chestertown, MD 21620
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
Respected by artists & collectors throughout the Mid-Atlantic region for over 30 years.
410-778-7330
203 High Street, 2nd Floor
Chestertown
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 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
Chestertown MD 21620
Days Open
All
Hours
Mon - Sat 10 am - 5 pm, Sun 11 am - 4 pm
DCA Member
410 -996-4776
236 Cannon St
Chestertown. MD 2160
Chestertown. MD 2160
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon - Thurs 8am - 4pm//Fri 8am - 6 pm PIZZA/Sat 8am - 2pm
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
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
443 679 3500
312 Park Row
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Mon, Thurs, Fri, Sat
Hours
9 am - 5 pm
DCA Member
443. 480. 5798
107 South Cross Sr.
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
10 AM - 5 PM
DCA Member
Unique handmade gifts made from local Maryland Artisans.
410-778-2073
Business Fax
410-778-2074
227 High Street
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
Hours
Mon- Fri: 10am - 5pm. Sat 10 am - 2pm
DCA Member
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
Business Tags
207 So. Cross Street,
Chestertown, MD 21620
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)
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.
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
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
443-282-0011
200 High St
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Tues, Wed, Thurs, Fri, Sat
Hours
Sun 11 am - 4 pm/Tues - Sat 10 am - 5 pm
DCA Member
610-220-3588
329 Cannon Street
Chestertown MD 21620
Chestertown MD 21620
Days Open
Wed, Thurs, Fri, Sat
Hours
1 - 5 pm
DCA Member
(410) 885-6722
215 High St
Chestertown MD 21620
Chestertown MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Sat 9 am - 8 pm/ Sun 9 am - 4 pm/ Wed & Thurs 11 am - 4 pm/Fri 11 am - 8 pm
DCA Member
315 High St
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
All
Hours
11:30 AM - 9:30 PM
410-778-5954
105 S. Cross Street
Chestertown MD 21620
Chestertown MD 21620
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
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 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
Chestertown
Days Open
All
Hours
M - S -10:00 - 5:00, Sun. - 11:00 - 3:00
DCA Member
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
Business Tags
311 High Street
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
All
Hours
Mon - Thurs 9:30 - 5:30, Fri & Sat 9:30 - 7, Sun 11 - 3
DCA Member
410-778-3499
101 Church Alley
Chestertown MD 21620
Chestertown MD 21620
DCA Member
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
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
Chestertown, Maryland 21620
Days Open
Mon, Tues, Wed, Thurs, Fri, Sat
DCA Member
443 867 8356
222 Devon Drive
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
All
Hours
website always open. Chestertown Farmers' Market Saturdays 8 am - noon
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
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
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
@tishfaplus
410 282 7551
Business Tags
343 High Street
Chestertown, MD 21620
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 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
Business Tags
111 S. Cross Street
Chestertown
Chestertown
Days Open
All
Hours
Mon-Sat: 10-5, Sunday: 12-4
DCA Member
Clothing. Furniture. Home Decor
Instagram
(410) 778-9000
321 High Street
Chestertown, MD 21620
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,
(443) 282-9797
337 High Street
Chestertown, MD 21620
Chestertown, MD 21620
Days Open
Sun, Wed, Thurs, Fri, Sat
Hours
Dinner Wed - Sat 5 - 9 pm//Lunch & Brunch Fri & Sat 11:30 - 2/Sun 11 - 2//Happy Hour Thurs - Sat 3 - 5:30
DCA Member
Open when the green light is on! Serving monthly Alfresco DInners in warm weather.
Occasional Live Music. Check FB page for more info
Occasional Live Music. Check FB page for more info
Business Tags
108 S Cross Street, 2nd Floor
Chestertown, MD 21620
Chestertown, MD 21620