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

I can't even comment on the coffee because we were turned away. After the Halloween parade this afternoon we wanted to grab coffee to warm up. After reaching the counter at 4:04pm, after walking through tables filled with customers enjoying coffee, we were turned away because they were closed. We proceeded to walk around the corner to a busy dunkin donuts who was happy to have our business. read more

Coffe, wine, beer, casual lunches all in one? Doable? Most certainly. And all with an atmosphere of a west coast cafe. Very Portland/Seattle-esque. And the sandwiches are amazing. Looks like they have a somewhat extensive collection of homemade baked goods for the morning crowd or for an afternoon snack. Maybe add a small cheese selection for that afternoon glass of wine. Friendly. Local, comfortable hangout. I'll be back again when in town to meet a long-time friend who lives in the area. Great find. read more

Play It Again Sam is an awesome coffee shop. Great coffee, sandwiches, baked goods, etc. Very friendly staff. Wonderful atmosphere.

Hello, why are you closed by 4 in the afternoon? People need their caffeine!

I've been coming here since I was a teenager, and I absolutely love it. It has such a great atmosphere, and everyone is always so friendly. I love sitting outside in the Spring & Summer, eating my food and watching the cars pass by. I feel like I'll never outgrow this place. read more

Play It Again Sam is a wonderful coffee shop full of awesome people. The coffee, food and atmosphere is amazing. The environment is eclectic, and full of fun. There is outdoor seating in the front and the rear of the shop. Inside the chairs are comfortable and you can bring your computer for the Wifi. If you want to relax and enjoy the scenery with a good cup of coffee and food, Play It Again Sam is the place. read more

They open at 7am, but the nice gentleman let me in at 6:30am when he saw me waiting in my car. I had already been driving 2 hours and was exhausted, so it was much appreciated. This is exactly the kind of service that earns an extra star in my book. I ordered a delicious cafe au lait with soy. The smooth coffee, obliging staff and the free wi fi are the reasoning behind my rating. Well done, Sam! I will certainly be back. read more

Pretty mediocre place. Sandwiches are basically cheap bread, cheap ham, cheap cheese and are in the $10 vicinity. Coffee is pretty bad and it's always dirty. A grungy coffee shop, however, can have its charm but the ownership and management can be pretty rude (not in the cool European way but in the passive aggressive annoying way). There ARE much much better options in Chestertown (e.g. Evergrain, around the corner). Play It Again Sam could be really cool, but just isn't. read more

play it again sam is a neat place to have breakfast and dinner! It may get crowded sometimes but the people and workers are friendly. I love their blt & avocado sandwich and spending the warm & sunny afternoon in their backyard. I go here as much as I can and I'm so glad I don't live far away! read more

Very cool, eclectic atmosphere. Friendly staff. Great coffee and goodies. Would definitely stop by again.

I ordered a milkshake here. They added a ton of ice cubes. Every time I come here I think it's good to support a small town coffee shop, but I'm always just a little disappointed in what ever I order. The coffee isn't bad, but the other drinks aren't great and the food is just okay. read more

Sadly, this coffee shop does not deliver as it could. The food and coffee is nothing special, and the environment is rather scruffy and looks like it needs professional help, a good cleaning and facelift. Too bad because we need a five-star coffee venue in Chestertown. read more

I love this place! Great coffee, espresso, tea, wine and fooooood. they get baked goods from the bakery in galena. theres Wi-Fi access so its a great place to get work done or just hang out! a wonderful place for meetings and conversation. read more

A cool gathering spot for young people of all ages. The perfect little place for inventive and delicious sandwiches, fresh brewed coffee, hot cocoa, or speciality teas, and a surprisingly good selection of beer and wine which you can buy by the bottle. Eight tables and one sofa of an assortment of styles nestled inside a comfortably small storefront plus a handful of chairs and tables on the sidewalk. College students, seniors, couples and even dogs (homemade biscuits!) are made to feel at home. Park along the street and begin a dayrtrip in Chestertown with a coffee and tasty treat from Sam's, walk about the town to visit the art galleries, bookstore and shops down and back to the waterfront, then end the tour with an artisanal sandwich, steaming soup, and wine. For the affordable price, life doesn't get much better. read more

Very cool place for all ages. Relax, enjoy the delicious coffee and free wifi.

Awesome sandwiches and drinks! Friendly staff. Cozy environment. Free wifi. A diamond in the rough. Will definitely come here every time I visit Chestertown! read more

Play it again Sam's is a great little coffee shop. It gets crowded at busy moments...the layout is not conducive to good flow. The coffee is good, wifi strong, service average. I have been disappointed by their bakery/pastry options - they are just provided by a "supplier." I think they could work harder at providing homemade or locally sourced snacks. read more

Play it Again Sam was recommended to my party after we discovered that another restaurant had an hour wait, and I can't say I was disappointed. The place was packed, but our food still arrived quickly. I had "the bad a--" sandwich, which was delicious, although I generally dislike avocado. They happened to be out of Brie to go on the sandwich someone in my group ordered, so they offered a complimentary gluten-free dessert that was quite good. It was a little loud--not great for quite conversation, but I'm sure that definitely had to do with the time of our visit. There was seating outdoors, but most of the chairs seemed to be missing, so availability was limited. read more

I had the best sandwich I have ever had at Play It Again Sam's a couple weekends ago! (BLT Avocado sandwich). Bacon was thick, juicy yet crispy, bread was fresh and soft, and all the ingredients tasted like they were just picked from the garden. SO delicious. It has left me craving it for weeks and I cannot wait to go back this weekend to get another one! read more

The food here is most excellent, the drinks are wonderful....however, it is a little pricey. It is a wonderful place to go to hang out, have lunch/breakfast, have a coffee/tea, etc. The atmosphere is generally calm and quiet, but it can get busy on occasion. It is a fairly unknown, yet also well-known place to be. Check it out! read more

Best sandwiches and smoothies in town. I go to the college in the town and visit at least once a week. All the staff are very friendly and willing to accommodate special requests. If you're passing through c-town, be certain to stop here! read more