Great breakfast or lunch spot!! Breakfast sandwiches, hot and cold lunch sandwiches, salads, coffee and smoothies. Plenty of seating spread out and super friendly staff!!! read more

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New location is awesome! Their coffee is delicious and breakfast offerings were great! They have gluten free bread as an option as well. There is an outside seating area as well as plenty of tables and cozy couches inside. It is much more spacious than the prior location. Is it counter service, but all the employees were super friendly! Highly recommend! read more

Very good breakfast sandwiches. Wish they had hash browns or home fries, just some kind of a side. But, the sandwiches were very good.

They have GF bread for the amazing Norwegian smoked salmon sandwich! And are able to make their Alaskan frozen coffee decaf! My 2 favorite things so I will follow them anywhere. read more

Coffee was weak. Two ham and cheese sandwiches plus two coffees were $35. The place has high ceilings with hard surfaces so there's an echo like a train station read more

Went to the new location today. They moved but that won't keep me from going since I really enjoy the hot drinks and hot breakfast sandwiches. I like how they have a variety of hot drink options and can make smoothies as well which is nice when you have a kid who loves smoothies. I hope the new location brings them in more business. I love how big it is too and that when the weather gets warmer they will have the outdoor eating option. Customer service is always great by the way. Zero complaints : ) read more

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This used to be my favorite breakfast and lunch spot in Chestertown. And the food's still good and coffee (from Rise Up) is still great. And I know the recent move to a strip mall wasn't their choice but minimal effort was put into the new space build-out and Sam's, very sadly, has lost its soul. This storefront is like eating in an airplane hanger. Long and wide with very high ceilings, hard floors, nothing much on the walls, and one sad comfortable seating area; the rest is wood tables and chairs. Mid-morning on a Monday it was LOUD in there. Did you ever go to a Horn & Horn in the 80s? It's a lot like that. Watch a few episodes of Friends, y'all. Split this cavernous space into living rooms with couches, coffee tables, rugs (please, please some rugs to deaden the din). Cut off a third of the service counter, which goes on forever and feels super mass-production-line. Bring back the game tables. Put some of your old art back up on the walls, maybe build a few smaller rooms out of this huge one, and please drop in a lower ceiling to get rid of the warehouse effect--it's really fighting your brand. I'll be curious if this place stays busy when the weather gets nice and people can choose from several similar places with outdoor seating. And I really really hope Sam's brings back some of its charm--it wouldn't take a ton. We can get bagels, sandwiches and coffee almost anywhere. Give us back our cozy. read more

The service was so bad. Play it again Sam? More like never again Sam. I payed over 50 dollars for some of the poorest service i've ever received. My crew waited for 15 minutes, with more than half of the order missing. While waiting, we were asked what was being waited on. I felt uncomfortable and judged, a feeling a costumer should never have to feel. I understand little mistakes but the staffs unwillingness to work with me was disappointing. Number one rule in costumer service policies is that the costumer is never wrong. The workers body language and annoyance after not giving me MY order, is crazy. Food was fine, but i will not be returning. Ever. read more

I had them cater a continental breakfast for an event. The food was great and the service was outstanding. Many thanks to Carolyn for being so responsive. read more

Good coffee! Dairy free options, but not all flavors are. Went back for a 2nd cup! Hoping there are some vegan options other than pb&j soon. read more

Wow, I had a perfect lunch today. Perfect chicken salad on panini, crisp dill pickle, yummy potato chips, and fresh iced tea. Sam's is so cute, and the employees are chipper and friendly. Glad I stopped in. read more

Play It Again Sam - Chicken salad on panini, chips, pickle and iced tea. - Coffee & Tea Near Me - Chestertown, Maryland

I wanted to give this place a nice review since my wife went to college in this town and had fond memories of this place. Unfortunately, if they cared 1/2 as much about their product food/drink as much as they cared about shutting down early and closing the store up they might have something special in such a quaint little cute town. Hours are weird, clientele is weird, and it seems run by miserable folk and college kids. I am trying to scarf down my meal while getting runned out since you are "closing" and now I have to worry about you guys turning the lights out on me and tripping over a vacuum cleaner. It's a sad thing, this place could be really cute. read more

I used to love this place, but the service has declined so much! I stopped in recently fifteen minutes before closing and they couldn't make me a sandwich! They said they shut everything down. The manager/owner? is also very off-putting because she looks miserable! The old owner was nice, funny and made patrons feel welcome. She also talks to her staff, especially, young ones, disrespectfully. I know kids need coaching, but I was so uncomfortable witnessing this, I probably will not return. There is a right way to speak to employees and the manager hasn't learned it or just doesn't care. The food is still fairly good but they recently added on a 3 % service fee for credit card purchase. This makes lunch there expensive! One more thing... They serve potato chips with the sandwiches which is great, but they are salt-free!! Ugh why? Every time I get them, I ask the staff for a salt shaker.. I seriously shake salt on the chips! Salty chips are the best compliment to a sandwich! read more

Play It Again Sam is a local coffee shop located in downtown Chestertown. Besides hot and cold beverages, the place also offers breakfast bagels, sandwiches, and pastries. I ordered a small Spice Chai with whole milk - this was super creamy, thick, and foamy, but a little more on the sweeter side. Served hot, it was a great beverage for a cold day. I also ordered a 'Lobster Tail' pastry, also known as a sfogliatella - this is a layered pastry that looks like a lobster tail, filled with cream and topped with more cream and a maraschino cherry. The staff here are super friendly, and they deliver your food/drinks to your table. The atmosphere is laid back and relaxing, and it's a great place to unwind a bit, do some work, or to study. Plenty of parking along Cross. +good Spice Chai :D +free wi-fi +friendly staff +parking along Cross read more

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Nice spot to get a cup of coffee but I can't say it's following all the covid protocols. If your employees are going to wear latex gloves and prepare food, they shouldn't be touching their phones with the same gloves. It defeats the purpose. Stay safe everyone. read more

If you want to get a quick bite, this is the place to go. Most people were sitting at the handful of tables outside. There are about 8 tables inside. Some 2 seaters and a few 4 seaters. Very limited breakfast menu but it was perfect for us since we had limited time for breakfast. You go up to the counter and order. The employees are very nice and the service was quick. They offered egg sandwiches on your choice of toast, roll or bagel. I was pleasantly surprised as to how good the sandwich was. I had an egg and cheese on an everything bagel. Bagel was toasted perfectly and the cheese melted nicely. The only thing is the bagel seemed very salty. My other 2 parties had the same thing, one with bacon and the other with sausage patty. Normally in restaurants, bacon is cooked soft. I personally like my bacon crunchy so if you want crispy bacon be sure to ask for it. Overall I gave it 4 stars because the tables were not cleaned between customers. I wiped my own tables off with clean napkins that were left on another table. read more

customer service was just bad, antagonizing customers that the employees knew personally. Terrible service! Rude staff, Will never return to this dump. Save your money and time - avoid at all costs! read more

Customer service was lacking. The cashier was more on her phone than taking my order. Wouldn't recommend

Coffee was not good and flies were in the place. Service was good but again coffee was not! read more

Do not order the Alaskan. I made a huge mistake thinking it's just like a milkshake. I really wanted to like/enjoy this place. I should have ordered just a plain coffee. My friends ordered a mocha that tasted more like a hot chocolate. And another friend ordered a strawberry smoothie. It tasted like artificial flavoring or too much sugar even though they said it was frozen strawberries. And too much ice. Not sure what it was but I was the one who pulled the trigger ordering an Alaskan after the un-amused cashier explained that it includes condensed milk, espresso, half & half and whipped cream. Sounded more like a milkshake but tasted like sugar on ice. And I had a good sugar headache for about the next few hours. read more

Not sure if the owner is insane or just flat out rude, but witnessing her berate teenage staff behind the counter over teachable moments, and make faces behind the backs of customers to show her "dislike" of them has made this establishment incredibly uncomfortable to visit. It's a shame, Sam's is a staple in Chestertown and has been for decades. read more

The coffee was delicious and the staff was helpful giving me directions to my destination.

The food is good but it's a shame everyone in there is miserable, rolling their eyes, no patience, attitude, that includes the owner. It kinda ruins the experience read more

Great coffee and good food. Bagels toasted with cream cheese and eggs. Yummy breakfast.

Food is inconsistent. I have had really good food there and not so good food. Always young teenage girls behind the counter with little or no experience with customer service and changes frequently. Lots of chatting among each other and not really interested in being there or helping customers. Overall not a bad place to go but every visit is different. read more

There aren't many shops in a small town, but who could miss a little local love? Serving not just coffee, but sandwiches, baked goods, and wine, this place was surprisingly steady-busy on an early afternoon in town. We ordered a Pumpkin Latte and Cappuccino. Our friends loved their Pumpkin Latte. I liked it, but thought it was a tad on the over-sweet side (they use the syrup pump) (possibly the type of soy milk they used). The Cappuccino was decent (nothing special). So many people around us were ordering sandwiches, which looked like hearty portions stacked with a side of potato chips (yum). I like this place for what it is: local coffee/sandwich shop. read more

If you wanna stop in for a cup of coffee or a fresh bagel this is the place. It's definitely the small town coffee shop, the atmosphere is great and I'd recommend it to anyone wanting a great cup of coffee. read more

Play It Again Sam - a menu on the wall - Coffee & Tea Near Me - Chestertown, Maryland

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4.5 stars! Spent an afternoon here in October 2016 while I had some time to kill. Needed a place with wifi to get some work done. I set up shop at one of the outdoor tables as it was a gorgeous fall day. Ordered a frozen hot chocolate and got down to business. Fast forward a few hours & I'm starving, so I leave my traveling office outside (Chestertown is the kind of place you can actually do this!) and head in to order some lunch. I got a turkey sandwich - which was basic but really tasty! Such a local vibe! Everyone in the place seemed to know each other by name (cue Cheers song). Cashiers were very friendly & sweet. Why isn't it 5 stars? Well, this is strange, but the girl who made my sandwich must've cut the bread before making the sandwich (fair enough, it was pretty thick). But unfortunately, she cut 1 piece of bread diagonally & 1 piece of bread into rectangles. I was so confused as first as to why I couldn't hold onto the sandwich! LOL. Also, I'd love to see a bit more selection. Maybe a few more desserts? Some more snack selections? Bags of chips, ice cream bars, granola bars, etc. Just a bit more to choose from. Other positives: Free wifi! Outlets, outlets, everywhere! They service Rise Up coffee, which is another small MD business, I love seeing this. read more

A really nice place in Chestertown, I stopped by here a total of 3 times and by the third time the barista already knew what I wanted, kudos to him. They have colorful outdoor seating right in front and they do a great job of making an iced mocha. This will be my go-to spot whenever I am in Chestertown next. read more

Play It Again Sam - My drink, and behind it a map - Coffee & Tea Near Me - Chestertown, Maryland

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Ripoff. Price gougers. $10.00 for a freakin roast beef sandwich? I know small businesses are hurting, but this is insane. Stick with the chains for this one. read more

Before head out on the Sultana breakfast was needed. Pass a couple options, when we came upon Play it Again Sam. They had outside seating and with the weather nice, that is were we sat. Ordered breakfast sandwiches (one on toast and one on a beagle) and drinks (one coffee and one juice) that did the job. They have a nice laid-back vibe, which is nice while having your breakfast on a wonderful spring day. read more

Play It Again Sam - Packets of real and fake sugar. - Coffee & Tea Near Me - Chestertown, Maryland

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this place. god dammit. food ok. espresso good. coffee ok. location outstanding. atmophere excellent. dont give up on this place. its had its ups and downs like the economy. ill never give up on Slay it Again Pams. its a core business in ol Festertown. but seriously: what the fuck are you guys doing to the drip coffee in here? they sell rise up coffee from easton which is really nice coffee. i dont know how they manage to butcher grounds+heated water= delicious. i manage to hit that formula out of the park every morning. and thats before i even have coffee. read more

Great coffee and cozy small coffee shop feel. We had bagels and avocado veggie sandwich. Sandwich was very fresh. Frozen hot chocolate also good. read more

Awesome coffee spot in a small town! Bagels are definitely delicious with all the different kinds of cream cheese! I have never really looked at prices to notice if they are expensive! The people inside are extremely welcoming! read more

Great food, great ambience. Still trying to figure out if new owner will like it herself? read more

This is definitely one of my most favorite cafes I've been to. The atmosphere is great, the art work and people they are wonderful. Every time I come there I have to order my favorite drink, an Alaskan. I would greatly recommend visiting Play It Again Sam if you are searching for a quality cafe to spend your time at. read more

This place rocks. By far, better than the Coffee Exchange in Providence, RI. The coffee delicious, the atmosphere is wonderful and the selections of wine is what blows anyone away. Friendly outstanding service. It doesn't make you feel out of place, by sitting outside at a table and enjoying the people walking by, the whole street is just architecturally pleasing. I make a point to go here whenever I visit. read more

Bustling, friendly local spot where I've been going for years. But lately it's so disorganized and understaffed that I've repeatedly ended up waiting 30+ minutes on an ordinary weekday for a very basic salad or sandwich that should take 90 seconds, max, to make. If they don't have their act together the next time I go in, they're going to lose this longtime customer. read more

This place is overhyped, there's no other cafe around for competition (Dunkin' Donuts doesn't count). I tried the mango smoothie, it is artificial-- not made from real mangoes. I saw the worker pour mango flavoring from a carton (beware, the strawberry smoothie is artificial too). It was overly sweet & gross, one can taste it is artificial without having prior knowledge. The drinks are overpriced, including the sandwiches. I don't come here unless it's with others who enjoy this place. read more

This place has changed since I went to school here... still it has some of the best coffee I have ever had (including their frozen coffee... the Alaskan), and it still has board games everywhere for people to enjoy... but now they have a wine selection... and on Friday afternoons when the weather is nice, there is nothing better than sitting outside and enjoying a bottle of wine with some friends along with some of the appetizers offered complementary to patrons. read more