Play It Again Sam

108 S Cross St B, Chestertown
(410) 778-2688

Recent Reviews

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Courtney Wallace

The homemade veggie cream cheese is to die for 🤤

Keyser S

Inconsistent service. Some days are good and some are very dissapointing.
It does not seem to have a structured process for preparing the food. I paid for a salad w/chx and avocado.
3 strips of chx and a quarter spoon of avocado.

Karla Aceves

I’m a little confused because I specially remember my order only being 13$. When I checked my bank account I was charged 16$. I only ordered a small ice coffee and a sandwich.

Letitia Getka

I was a big fan of the old location, it was so cozy and eclectic and welcoming. The new location is devoid of all charm - entirely too loud and not the least bit cozy. There is no personality. No art on the walls, no board games, no books - everything feels soulless and corporate. It could be a generic Starbucks-wannabe in any city. It’s so loud and echoing you can’t hear yourself think. Would benefit from some sound deadening features and some attempt at feeling cozy and original. You cannot sit at the bar to eat unless you’re unusually tall, the bar is too high up from the chairs. I ordered a cappuccino and it took like ten minutes to get my order. I went back and ordered a sandwich and it was only okay, not much meat on it for the high cost ($14). I will only get takeout from now on unless changes are made.

Charlie Wooters

The atmosphere was very welcoming and enjoyable. The menu was very fairly priced. The service was excellent and friendly. The food was very good, and portion size was more than expected when I ordered. I would definitely check them out again.

edward bradley

It’s like vending machine food eaten in an airport boarding area. The new place is not at all like the old Sam’s. A big disappointment.

Theresa Prete

The food and service is outstanding! The bread is amazing. I absolutely love the food.

Atmosphere: 5

Food: 5

Service: 5

Victoria Willoughby

the cookies are really good and everything is so good

Atmosphere: 5

Food: 5

Service: 5

Amanda Nichols

Favorite place to get breakfast in all of downtown!

Atmosphere: 5

Food: 5

Service: 5

Sharon Murdoch

The good: the food tasted good, and the new space is attractive. The bad: even though they were not particularly busy (I'd call it slowish but steady), every table was dirty. When we were called to pick up our food, the cinnamon roll we ordered was not with our other food. Oddly, they didn't seem to know how to serve it. I was glad I had decided not to order coffee, as several customers were standing at the counter waiting for the carafes to be filled. There were at least eight people working; it's hard to understand why there would be dirty tables and no coffee.

Atmosphere: 2

Food: 4

Service: 2

Gianna Boria

I recently had the pleasure of dining at Play It Again Sam’s, and I cannot recommend this spot enough! From the moment I walked in, I was greeted with a warm and welcoming atmosphere that set the tone for the entire experience. The service was exceptional—friendly, attentive, and genuinely positive.

We ordered the BLT sandwich and the chicken salad, and both dishes were absolutely delicious! The BLT was perfectly balanced with crispy bacon, fresh lettuce, and ripe tomatoes, all tucked between perfectly toasted bread. The chicken salad was light yet flavorful, with a great mix of textures and ingredients. We also tried their iced coffee, which was smooth, refreshing, and the perfect accompaniment to our meal.

Whether you’re looking for a cozy place to dine in or a great spot to grab a coffee, Play It Again Sam’s is definitely worth a visit. 10/10 would recommend!

Atmosphere: 5

Food: 5

Service: 5

James Slattery

Service was poor. Chicken salad was like mashed baby food. Sandwich was not cut fully so the halves could not be separated . All in all it was not a pleasant experience and will not return.

Atmosphere: 1

Food: 1

Service: 1

Sean Grimes

Soft bagels, loaded breakfast sandwich, decent prices. Perfect before the long drive north.

Atmosphere: 5

Food: 5

Service: 5

Dianne McCarthy

I had a bagel and chai tea. Not everyone can make a good chai tea and they hit it on the head.

Atmosphere: 5

Food: 5

Service: 5

Britt Raybuck

My favorite coffee spot in C-Town.

They are super aware everytime to my dairy and caffeine sensitivities and intolerances. I appreciate them being mindful and always have a great tasting Iced Mocha Latte with oat milk and tell they are mindful on not cross contaminating.

The best breakfast grab that’s easy? Bacon and egg (with or without cheese, your choice!) is hands down awesome! Nice fluffy egg, crispy bacon on a thick bagel… can’t go wrong.

Honorable mentions? Nice wraps, enjoy the Greek salad - you totally get a great portion size!

Always love coming here when in town, taking a bike ride and want a place to hangout ?

Atmosphere: 5

Food: 5

Service: 5

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