Chester River Wine & Cheese Co.

We love popping in to Chester River Wine & Cheese! When we are in need of high quality, delicious cheese, we know where to go. Whether we are hosting and want to put together some yummy treats for our guests, or simply looking for ourselves, we always are delighted with what we get here. They are happy to help you curate your charcuterie board and suggest meats and cheeses based upon your preferences! They have a selection of everything you could need to complete your hosting needs! From display/cutting boards to cheese knives, crackers, napkins - you name it!

We've been to the owners wife's shop in Annapolis and while in chestertown this past weekend we saw she has a shop in chestertown as well so we went in and got a few things and she told us about her husband's shop so we walked up the street and oh my gosh this place is amazing. The owner and staff are so friendly and knowledgeable and super helpful. There is a nice selection of items that you don't find just everywhere. We tried a few cheeses that he recommended and they were absolutely amazing. Specifically the garlic and herb la ruelle (hope I spelled that right lol) I live in Hampstead so I'm a good 2 hours away and already I'm talking to my boyfriend about how we need to drive back up there just to get some more cheese lol it's that good we took it home and made everyone try it and it was gone in 5 minutes everyone loved it and could not believe how good it was. He also recommended a wine for us and we ended up getting two bottles of it and everyone loved that as well. So I highly recommend this shop and then when you're done I highly recommend walking down the street to his wife's shop because she has an amazing selection of items for the home and clothing and accessories. I have an obsession with mushrooms so I saw a ceramic mushroom decoration in the window and had to get it lol and we also picked up something for my mom for her birthday which she loved. Couldn't meet two nicer people so definitely do yourself a favor and check out both shops.

The most delightful experience every time. Personal service, delectable offerings and more. The owners take such care in cultivating their inventory and atmosphere. We count in them for all of our cravings! Big city offerings in a small.town. We’re so.lucky to have them here! Highly recommend.

John and Jenn have built a very nice business. The wines and the cheeses are a good combination of the old standbys and something new and interesting. Service is top-notch and friendly.

Have visited both Chester River Wine and Cheese and Welcome Home many times and the experience has always been wonderful. Most recently I bought a gift certificate for a friend's birthday and he and his wife "had a ball" using it. Jenn and John helped them find the perfect things for a birthday dinner! Thanks, Jenn and John!

Will not allow properly ID'ed service dogs on premises! Total ignorance of the law and NOT willing to confirm to national ADA rules. Ignorant and insulting! I am NOT angry and did not speak with you disrespectfully. I am merely disappointed. WE DID want to make a purchase but my wife and I were put off at your behavior. I DID answer your questions as required and only received silence so we left. PLEASE don't do this again with those needing the assistance of a service dog.

My now wife and I visited the store multiple times this summer leading up to our wedding this past weekend. The staff were always pleasant, inviting, and knowledgeable on all the products in the store. We purchased wine, cheese, olives, chips, jarred caramel and jams on our stops in the store. On our last visit prior to our wedding, the owners gave us a gift bottle of rose wine. We will definitely return on our next visit to C-town.

What a gem! They have a great selection of wines from around the world at nice prices. They also have a gorgeous selection of cheeses, meats, and antipasti. The owners are I'm a big fan! Lovely owners who know their products and can make excellent suggestions.

Chester River Wine & Cheese is a small boutique specialty market that offers various kitchen tools, domestic & international wine, retail gourmet food items (such as handmade jam, mustard, salts, olives, etc.), cut-to-order cheeses (!), wine & cheese boards, and serveware. I stopped by to pick up some cheeses, and Tara was readily available to make great recommendations and suggestions! My favorite, Fromage d'Affinois was available, which was buttery and super creamy; I'd also picked up some Vacherousse d'Argental, another soft cheese, was creamy and had a nice little salty bite to it. To complement them both, I picked up some English biscuits as well as a recommended strawberry preserve, imported from France! The market/cheese shop is super cute, and I highly recommend in stopping by for gifts and/or picking up things for picnics/appetizers! +boutique specialty market +great modest cheese selections +imported gourmet items +ask for Tara :D +free parking along Cross

Yes! Beautiful cheese & wine. You have to buy a gift bag for the wine, but otherwise superior!

We came in here during a visit To Chestertown. The owner was so friendly and extremely helpful explaining the different cheeses to us. We went with her recommendations and it was some of the most delicious cheese I've ever had! It's a very cute shoppe with other fun goodies--we also grabbed some cookies and crackers. Will Definitley be back the next time we stop in Chestertown! Thank you!

I waited over 15 minutes for the one person working the store on a Saturday afternoon to serve one piece of cheese (in addition to some things they picked out themselves) to a couple in front of me - she offered them a free ice pack, packed and repacked their bag, talked casually about how glad she was that a store order she made got messed up and they received something people really like instead, forgot to ring up their wine and then did a second transaction, etc. All this wouldn't be an issue for me if all customers got great treatment. However, at no point in waiting for them did she even acknowledge my presence, which should have been a warning for me. Finally she was done with them and I told her I wanted cheddar cheese - they had two kinds, and I wasn't sure how much I wanted of each. She weighed how much was left of the blocks and told me - which didn't really help me decide how much I wanted, so I decided myself. If I had gotten the same customer service as the couple before me she would have asked me what I was using it for, how long my car ride was, how many people I would be serving. But, nop, nothing. Just what the blocks currently weighed. Then she told me they couldn't slice it. So I didnt buy the $30/lb cheese that was in a case right next to a slicer. You know the feeling in your gut that you're not getting equal treatment in a store? If you don't know what I'm talking about, you'll probably be OK here. But if you do know the feeling, avoid this place and save your money on the overpriced cheese and wine anyway.

I am dismayed by Robert's post below. I was in the store with him during his "incident." I was actually the customer who shut the door when Robert refused to comply with this simple request. I walked over, shut the door, and returned to the register. It was a tenuous 30 seconds of my life that I will never have back. The owner explained her very appropriate reasoning. The door is on an old building full of character - one that is welcoming, appropriate, and characteristic of a quaint wine and cheese shop. Its not conducive to an automatic closer. Additionally, as Robert could see, Jen has mobility issues. As a parent of a child with similar mobility issues, shame on you Robert. Her explanation for the request to shut the door had nothing to do with this (she is more than capable of running the store), but I would characterize someone who engages in that type of behavior as a bully. Just shut the front door. Your comments bordered on misogynistic and degrading toward women. Given you were the only man, it began to feel like an attack on the women in the shop. Its odd to me that when a woman makes a simple request one time, such as "Please close the door," and it is characterized as bossy, but if a man made the request, would you call him bossy also? I applaud Jen and John for running a lovely shop. I prefer to support local businesses in my town and build up one another. I couldn't think of a better place to get a lovely triple crème brie, bufalleto, a round of bijou aged goat, or an inventive pate. They also have lovely pasta and meats. The wine pairing suggestions are consistently on-point and affordably priced. They work extremely hard for each dollar they earn, and they will continue to earn mine.

I am appalled at Robert S's review. I even went so far as to join Yelp just to refute his bad review! Fortunately, his narration of events reflects much worse on him than it does on Jenn or on Chester River Wine & Cheese. By his own description, his behavior was inexcusable, bullying, and misogynist. There was no need for a conflict, yet he created one. The Wine and Cheese shop is not the only vibrant, bustling business in town that requires customers to close the door behind them. Evergrain does, with a sign on the door. Twiggs and Teacups asks you to please leave your beverage on a table outside the shop, and both Twigs and The Bookplate remind you with a sign to close the door behind you, so the cats don't get out. Does Robert S go into these shops to badger and bully the owners and staff because of it? These are old buildings, and because of their location in the historic district. Many of us appreciate the charm of these buildings, and certainly most of us have no problem closing the door behind us. Jenn and John, both as community members and business owners have been a wonderful addition to our small town. They have brought us two excellently executed small shops, and have been very active and dedicated to improving the town's business environment, as well as supporting local events. I love this shop, I love their passion, and the hard work and dedication they bring to everything they do. The selection of cheeses and wines punch well above the weight of our tiny little Eastern Shore town. In the era of "Big Boxification", I'm glad we have a little shop with wood floors that creak and a door I have to close behind me, a place where I can sample a nice goat cheese before I buy, or even just say, "I need a cheese for ..." and be guided to just the right thing that I didn't know I was looking for. Jenn and John, keep doing what you're doing!

Went in to buy cheese and the door did not close behind me and the owner asked me to close the door. When I went to close the door another customer closed it. I suggested to the owner that a door stop could be added to avoid this problem. The owner said "she wanted the customer to close it". I proceeded to tell her that she was being bossy. She then informed me to leave the shop. Guess she does not need my business or other peoples.

LOVE this shop! Wines are always reasonable priced and well chosen. We ordered our 1st charcuterie tray for Thanksgiving and loved the choices! It will become an addition to our holiday traditions.

Exceptional choices of cheeses, salamis & wines to choose from. A ton of unique ingredients and great little kitchen & entertaining knock knacks to buy. Have been here 2 or 3 times. Great ambiance! Sit with a kid, friends, relax. The cheese & charcuterie plates are delicious! Take your time. Not a rushed kind of place.

I love this shop! Everyone that works here is super friendly and knowledgeable about their cheese and wine selections. Jenn helped me pick out a perfect wine to pair with a special dinner. She also made sure I tried their delicious drunken goat cheese. I was really impressed with their care in labeling the cheese with notes if it is vegan or not. I also appreciate their willingness to special order stuff if they don't already have it. They do wine tastings with spectacular cheese and charcuterie that is over the top good. I love this shop!

It's a special place. The quality of all the products is exceptional. Do take the opportunity to sit and dine there and be wowed by the selection of meats, cheeses, wines and tapas. The perfect date! And what is so important but may sometimes be taken for granted: the owners and staff. Always knowledgeable and always kind. This is a true gem in Chestertown and would rival the best in Washington, New York, or London.

This is a very good addition to any civilized town! Who doesn't need a purveyor of wine and cheese? Between this shop and Evergrain Bread, you're set. Good selection of olives and pickled treats, too. Cheers!

I just love this store so much. It's added a flair of pizazz to Chestertown's offerings -- great wine and AMAZING cheeses. Oh Lord, I have to control myself when I go in there because I want one of everything -- and they let you sample it all! Jenn and John quickly became town favorites because of their warmth, charm, integrity, and dedication to good service, great products, and being big boosters of our local economy and the success of our great little community. Nothing about your experience at this shop will disappoint.

So we stumbled across this place while on a mini vacay for our anniversary. What a gem. Jenn and John are absolutely delightful. Very welcoming and conversational. Knowledgeable about their products AND COVID compliant. My husband and I visited this place everyday we were in the area trying their recommendations and enjoying their company. Jenn and John, you made us feel right at home. Can't wait to visit again soon.

Chester River Wine & Cheese is one of my favorite shops in Chestertown. It's the perfect place to stop if you need a gift for a foodie, want to sit and enjoy a cheese board and perfectly paired wines, or want to bring home a delectable assortment of goodies. Jenn, John and their marvelous team are eager to share their love and knowledge of all things wine and cheese and will help you find exactly what you are looking for. John helped me put together an amazing gift basket for my in-laws filled to the brim with wine, cheese, artisan crackers, chocolates and sweets that they still rave about. I highly recommend a visit!

There isn't anything you won't find in this beautiful shop in downtown Chestertown. Owners are impeccable and service always comes with a smile. The selection is as good as any of the top shops in DC area. Wine and cheese selections are excellent. Stop by every time you are in Chestertown. I always do and the jams are my teens favorite!

Chestertown is so lucky to have this fantastic shop. I live in New York City and have to travel miles to have access to all of the goods that are available in this one place. John and Jenn clearly love their community and have done so much to raise the bar on what Chestertown can offer its residents and visitors.

Stopped by tonight for Mid-Week Sips with Jenn and John (Wednesdays from 4:30-6:30). On the menu tonight was 5 small plates, a cheese plate and a charcuterie plate. We ordered the cheese plate, poached shrimp plate and the poached fig and goat cheese crostinis. Everything was perfect and served quickly. They offer wine by the glass, bottled beer and any bottle they have in the store with no corkage fee! Definitely a downtown treasure and the owners/staff are very knowledgeable, pleasant and helpful.

What a wonderful source for wine and great food. The staff illustrates the owner's compassion for great service and knowledge of the wine and delicious food offerings; they truly appreciate each and every person who walks in the shop. Spending time in the shop is time well spent; we go every time we are in Chestertown.

Absolutely love this shop! Not only do they have a wonderful selection of wine, cheeses, and pâté, but they also have amazing crackers, and spreads, and small gifts. The service is excellent and everyone that works there, including the owners, are very kind and helpful. We had lunch there today and it was delicious. You must visit this shop while you are in Chestertown!!

Warm, welcoming, and full of delicious treats--what a special place! Whether you're throwing a party for 20 picky eaters or want the perfect wine and cheese for a Wednesday pick-me-up, the knowledgable owners and staff at this store will help you find exactly the right thing. And if you ever need to order a cheese plate for a function, Jenn takes cheese art to the next level! This little shop around the corner helps Chestertown feel like home. We're so lucky to have a store of this caliber on Cross St.

This place has it all - great wine selection, delicious cheeses and meats, a nice selection of frozen pasta items and a knowledgeable staff. However, they should find a new pimento cheese recipe or call the stuff they are selling something else. It's not pimento cheese and not to my liking. Here's a suggestion...Andrew Knowlton (a true southerner) has a real southern, perfectly delicious, pimiento cheese recipe on Epicurious.com.

This is a wonderful place to unwind, or to gather fixings for an incredible feast at home. Besides the fact that the products here are truly amazing, the owners, Jen and John, are two of the most lovely people in Chestertown. They serve their customers with an earnestness and generosity that is unparalleled. I always leave this place satisfied and smiling!

Really no better place to prepare for a dinner party or a quiet evening on the porch. John & Jen really know how to stock their store for all income levels... Special occasion wines, and "house wines" of the best quality! And oh the cheeses and meats!!! YUM.

This is an awesome little shop with delicious cheeses and meat. The best charcuterie I've ever had with amazing wine selections. I can't wait to go back.

Bad customer service. Waited a while and was never acknowledged. Store has a snobby feel.

Nice start up. They have some unique cheesesno found it with my while to give them some business to support the downtown

A new wine & cheese shop that also has a few gourmet food items, John and Jennifer have put together a nice collection of cheeses, including some tasty unpasteurized ones, as well as nice wines from off-the beaten path regions at reasonable price points. They have tastings on Saturday, and John & Jennifer are very friendly and love to have customers sample food items in the store.

A great place for sidewalk snacking on wonderful cheeses, pates and salami. Good service with a wide varietythat changes regularly. For the money, you can't beat it. It's a great way to spend an afternoon.

The best wine, cheese and specialty foods around. The nicest owners too. They are so knowledgeable. If you describe the dinner you are making or the event you are hosting, they will have several suggestions, which have always been spot on. I can't go a week without stopping in.

Awesome place- amazing selection of cheese from alll over. Great selection of good, affordable wine - to help you pay for the cheese! - great gifts and more... we spend a lot of time and money here all summer as it is so yummy.

While visiting Chestertown my husband and I wandered into the shop and had a wonderful time. The staff was incredibly helpful and walked us through the store's offerings and menu. we stayed for a glass of wine and cheese/salami plate and really had a lovely time. Everyone there was very nice and the selection was quite good. It was just a wonderful way to spend some time while visiting Chestertown.