Gourmet Food | Wine | Spirits

Grab a seat at our table or take one home to yours

Mezze Platter - $10

Inspired by Mediterranean and Middle Eastern cuisine, this board is packed with healthy flavor. The board includes two house-made spreads, a house-marinated feta, and fresh vegetables. 

Cheese & Fruit Plate - $10

For the cheese lover who needs a mid-day nosh. You'll get to pick  two of our most popular cheeses. We'll pair it with a fabulous spread, fresh fruit, olive tapenade, and delicious crackers. 

Wine Tasting Events

Every Saturday Morning

Join us in the wine and cheese shop every Saturday from 11-5 for complementary samples of wines from our current collection.

Summer Rosé Tasting: May 19

Join us for our Summer Rosé Tasting Party on May 19 from 5 - 8 p.m. 

Welcome the start of summer as we introduce our 2018 rosé collection. Enjoy food, music, laughter, and fun as well as sips of our hand-selected collection of the best rosé on the Upper Eastern Shore.

Fall Wine Tasting: September 22

The air is crisp and the flavors of the season are changing as the bounty of our home garden comes to an end. Join us to explore wines that will be delicious for sipping by the fire pit or alongside your roasted root vegetables and chicken dinner.

Thanksgiving Wine Tasting: November 10

Thanksgiving is all about family, friends, food, and laughter - and every family has their signature dish or meal. Regardless of your family tradition, there is an amazing wine that will make your meal absolutely perfect. Join us in the shop to explore our picks for the perfect Thanksgiving Dinner!

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. 


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.  

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