Gourmet Food | Wine | Spirits

Let's Play with our food!

Cheese & Charcuterie

In our cheese case you'll find over 90 types of domestic & international cut-to-order cheese, salami, charcuterie, pate and sausages. Always ask for samples - we want you to love your cheese as much as we do. 

Oils, Spices, & Vinegars

Just inside the door you'll find oil fustis &  vinegars, salts & spices, and ready to consume salad dressing and marinades. We specialize in unique, small batch producers. Check out the aged balsamic! 

Pork, Beef, Duck, & Lamb

We are proud to partner with Langenfelder Pork, and St. Brigid's Farm to offer locally raised pork & beef. We also partner with D'Artagnan to offer duck and lamb. Special orders are welcome! 

Pastas & Grains

As former Philly residents we're tickled and delighted to offer Tallutos gourmet pasta. We also offer a diverse selection of imported dry pasta and grains. 


We sample every wine carried in our store. Many of our wines are unique to Kent County and the Upper Eastern Shore. We offer a 10% mixed case discount and 20% discount on single label pre-order wines. 

Order a cheese board


We have a small but diverse collection of spirits and handcrafted mixers. Our team can help you create an excellent cocktail (or mocktail) for your next party or event.  Case discounts available.  

Wine, Sprits, & Beer Tasting Events

December 7

Join us Friday, December 7th during First Friday and the launch of the Dickens of a Christmas Festival. We are pouring complementary wine tastings in the shop from 5-8 p.m. We are also hosting a guest oyster shucker and serving up delicious cheese boards, wine by the glass, and special noshes.

December 8

On Saturday, December 8th the Dickens Festival is in full swing. Visit us at the shop for a traditional Ploughman's lunch. We're serving up crusty bread, cheese, ham, and pickles alongside hearty soups and tinned fish. (for a less Victorian experience, sandwiches are also available). 

Read about us in Edible Delmarva

About Us

We carry the best wine and gourmet foods on the Upper Eastern Shore.

We taste every product and hand-select only those bottles or foods we would serve to our guests. We want you to feel confident that the food, wine, and sprits in our shop are of the highest quality, which is why we encourage you to taste before you buy. 

We're focused on you.

As management consultants turned small town business owners, we're focused on your needs. You'll find us in our business almost every day, ready to help you create an amazing meal or wonderful memory. 

We'll help you get from dinner to bed.

In addition to our gourmet food store, we also own Welcome Home, Chestertown's kitchen, bed, and bath store. 

Visit our kitchen, bed, and bath store, Welcome Home

Contact Us

Drop us a line!

Located in the historic arts & entertainment district of Chestertown on the Upper Eastern Shore...

Our shop is universally accessible via a garden entrance along the Cannon St. side of our building. Please ring the doorbell for assistance. We also have a public ADA restroom. 

Chester River Wine & Cheese Co.

117 S. Cross St., Chestertown MD

(443) 282-0220


Closed Christmas & New Years Day

Keep in touch!

Store Return Policy

Returns are accepted within 10 business days of purchase, unused, in the original packaging to the original store of purchase. All returns are processed using the original method of payment. We are unable to accept the return of frozen or refrigerated food, gift cards, or wine.  

With thanks for your patronage,

Jenn & John