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
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.
Days Open: Wed, Thurs, Fri, Sat
Hours: Wednesday through Saturday, 4 pm to 9 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
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!
Days Open: Tues, Wed, Thurs, Fri, Sat
Hours: Tuesday -through Saturday, 8 am – 2 pm
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.
Days Open: All
Hours: Monday – Saturday, 11:30 am – 9 pm, Sunday Brunch 10 am – 3 pm, DInner 5 pm – 9 pm
DCA Member