Gourmet Food | Wine | Spirits

happy Holidays


Join us November 15-22 from 11-5 daily for an in-store Thanksgiving Wine Tasting. We've hand selected wines pair well with a traditional Thanksgiving meal. We're delighted to offer guests a mixed half case 10% discount on wines we are tasting during the event. 

Our Thanksgiving Wine Tasting includes:


  • Rosé Bernard Brut Rosé, France 
  • Delicio Rosato, Portugal 


  • Cellier, Chardonnay / Viognier, France
  • Noble Hill, Sauvignon Blanc, South Africa
  • AltoLandon, Moscatel, Spain


  • Le Tripoteur, Blend, France 
  • Natte Valley, Cinsault, South Africa
  • Les Brebis, Pinot Noir, Oregon 
  • Ch. De Panigon, Blend, France


  • Quady, Black Muscat, California

We are open 8am - 12pm Thanksgiving morning for your last minute food and wine needs. 

"Black Friday"

Stretch your legs and stroll Historic Chestertown before heading home for a leftover turkey an stuffing sandwich. The shop is open 10am - 6pm. 

"Small Busines Saturday"

Grab the Downtown Chestertown Association shopping passport at the Farmer's Market - or any shop in town. Get your passport stamped for great deals and a chance to win an awesome prize basket. 

At Chester River Wine & Cheese and Welcome Home we are offering a $10 gift card with $75 purchase. We've donated two $50 gift cards and a handmade set of towels to the prize baskets. 

Dickens of a Christmas

Join us in historic Chestertown December 1 - 3 for our very first Dickens of a Christmas festival. 

On Saturday, December 2, join us from 11-2 for a Ploughman's Lunch. A Ploughman's Lunch is a traditional meal of bread, cheese and spirits for rural farm workers. Chester River kicks it up a notch and offers a Cheese board, meat/veggie hand pies plus a FREE wine and hard cider tasting. Guests may purchase non-alcohol cider. Hearty and delicious!  

Remember that amazing shopping passport from Small Business Saturday? Well, grab another - we're offering the same great deals and guests will have another chance to win when they shop with our small businesses! 

Twas the Week Before Christmas

...and you've got a million things to do. In addition to our normal business hours, Chester River Wine & Cheese is open Monday, December 18. Welcome Home is open until 7pm every evening the week before Christmas. Both stores are closed Christmas day. 

Happy New Year!!!

Grab a bottle of sparkling wine and have a blast! We're open New Years Eve from 11am - 4pm. 

We are closed Monday, January 1 and Tuesday, January 2. 

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're fastidious.

We taste every product. We want you to feel confident that the food, wine, and sprits in our shop are of the highest quality.

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


Tue - Sat: 10am - 6pm

Sun: 11am - 4pm

Mon: Closed

Open Thanksgiving 8 - 12 | 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