- Art Gallery (4)
- Artists (2)
- Bakery (3)
- Bank (2)
- Bar with Food (2)
- Education (2)
- Event Venue (2)
- Gourmet Food (2)
- Grocery (1)
- Lodging (4)
- Media (1)
- Package Store (1)
- Pets (1)
- Realtor (2)
- Restaurant (7)
- Services (7)
- Shops (12)
- The Arts (1)
- Vineyards (2)
At Ananda Psychiatry and Wellness, we provide compassionate medication management, tailored to individuals ages 10 and up. Whether it's via telehealth or in-person in Harford County, Maryland, we are committed to your well-being.
At our small, family-owned practice, you receive comprehensive care with a personal touch, ensuring continuity and understanding of your medical history and needs.
Our goal is to ensure that you feel supported and empowered on your journey to mental wellness. Your story is important to us, and we are here to help you through every step.
Together, let's create a path to vitality and peace of mind. Your well-being is our priority.
https://www.ananda-psychiatry.com/
info@ananda-psychiatry.com
410-870-8318
At our small, family-owned practice, you receive comprehensive care with a personal touch, ensuring continuity and understanding of your medical history and needs.
Our goal is to ensure that you feel supported and empowered on your journey to mental wellness. Your story is important to us, and we are here to help you through every step.
Together, let's create a path to vitality and peace of mind. Your well-being is our priority.
https://www.ananda-psychiatry.com/
info@ananda-psychiatry.com
410-870-8318
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
Wednesday, Thursday & Friday, 5 - 8 pm, Saturday Noon - 8 pm, Sunday 11 - 3
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
A quiet Bed and Breakfast less than a mile from Chestertown, Maryland.
410-778-1860
Business Tags
25227 Chestertown Road
Chestertown, Maryland 21620
Chestertown, Maryland 21620
Days Open
All
DCA Member
Taste the Difference!
329 Cannon St, Chestertown, MD
briansbestpastries.com
(800) 399-9658
Mon
Closed
Tue
Closed
Wed
08:00 am – 04:30 pm
Thu
08:00 am – 04:30 pm
Fri
08:00 am – 04:30 pm
Sat
08:00 am – 04:30 pm
Sun
10:00 am – 02:00 pm
329 Cannon St, Chestertown, MD
briansbestpastries.com
(800) 399-9658
Mon
Closed
Tue
Closed
Wed
08:00 am – 04:30 pm
Thu
08:00 am – 04:30 pm
Fri
08:00 am – 04:30 pm
Sat
08:00 am – 04:30 pm
Sun
10:00 am – 02:00 pm
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
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
Gallery 343 High Street
Wed - Fri 11 am - 3 pm
Sat 9 am - 2 pm
Store 200 B High Street
Wed - Fri 11 am - 3 pm
Sat 10 am - 2 pm
Clay Studio 204 High Street
Wed - Thurs 10 am - 6 pm
KidSPOT 343 High Street
Saturday 9 am - noon
Gallery 343 High Street
Wed - Fri 11 am - 3 pm
Sat 9 am - 2 pm
Store 200 B High Street
Wed - Fri 11 am - 3 pm
Sat 10 am - 2 pm
Clay Studio 204 High Street
Wed - Thurs 10 am - 6 pm
KidSPOT 343 High Street
Saturday 9 am - noon
310 778 6300
343 High Street,
Chestertown, MD 21620
Chestertown, MD 21620
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
302.304.0551
12441 Vansants Corner Rdt
Kennedyville, MD 21645
Kennedyville, MD 21645
Days Open
All
DCA Member
410 810 0010
227 1/2 High St
Chestertown MD 21620
Chestertown MD 21620
Days Open
All
Hours
9 am - 7 pm
DCA Member
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) 778-3965
Business Tags
335 High St
Chestertown, MD 21620
Chestertown, MD 21620
DCA Member
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
113 S. Cross St.
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
Ride Like Royalty!
Serving Maryland SInce 1994
Family Owned
Weddings
Airport
Special Events
Group Trips
Serving Maryland SInce 1994
Family Owned
Weddings
Airport
Special Events
Group Trips
410 778 4860
920 Thompson Creek Rd
Stevensville, MD
Stevensville, MD
Days Open
All
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
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
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 - Sat: 9:30 - 5:30, Sun: 11 - 3, First Friday until 7PM
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
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
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
(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
