Play It Again Sam

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.

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.

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

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.

This place is overhyped, there’s no other café 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.

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.

A very nice place to get coffee. The staff are friendly, the food and drinks are prepared well and quickly, and the atmosphere allows you to relax and take your time. I’ve been here three times now, and have enjoyed myself each time and plan to return when I can.

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

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.

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

Coffe, wine, beer, casual lunches all in one? Doable? Most certainly. And all with an atmosphere of a west coast café. 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.

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!

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 café 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.

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

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.

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!

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

Dog Friendly. Anywhere I can take my dog I am happy

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.

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.