Play It Again Sam

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

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Bag of Rise Up Coffee

Homemade Ice Cream

Mocha Latte Small

Turkey and Swiss

Veggie Sandwich

Ham and Cheddar

Egg and Cheese

Red Eye Medium

Chicken Caesar

Chicken Salad

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Recent Reviews

I would love to give Sam’s a higher review, but ever since the move to the new location, it simply doesn’t have the warm, inviting vibe it previously did. The food & drinks are good, pretty pricey for some things but generally good quality. Usually the person taking the orders seems pretty disinterested and although i’ve never had a “rude” employee, the customer service & enthusiasm is lacking a bit. My biggest qualm is really the environment/decor. The place...

January 2026

My first time at the new location, and appreciate they moved to a larger space. The old location was cramped and crowded, and the new space is spread out. I had a hot roast beef and brie sandwich, and it was as good as before. Good food and good service! The bare painted walls look a bit sterile, and it would look nice decorated with photos or artwork.

September 2025

I used to really like visiting Play it Again Sam when it was in the center of town (or close to it) but always got frustrated by the size of the restaurant as it was quite small and frequently too busy to accommodate the morning rush.

They moved to this new building and I like it. It's huge compared to the old place. The menu has gotten as big as the building and the 3 or 4 dishes we've had (my wife and me) have been tasty. The coffee from Rise Up...

August 2025

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Restaurants in Chestertown, MD

Play It Again Sam

Customers' Favorites

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Play It Again Sam