Play It Again Sam

Chestertown, MD · Restaurant

Rating
4.3/5
★★★★☆ 4.3
Reviews
20
Rank in Chestertown
#21
of 45 restaurants
City Percentile
36%
rating percentile
Address
Play It Again Sam, 14 Washington Square, Chestertown, MD 21620
Phone
(410) 778-2688
Website
playsitagainsam.com
Status
Closed · Opens 8 AM

Play It Again Sam is a restaurant located in Chestertown, MD. It is one of 45 restaurants listed in Chestertown. Its 4.3-star rating is slightly below the Chestertown city average of 4.4 stars. There are 10 photos associated with this location.

About Play It Again Sam

We serve coffee, espresso drinks, breakfast sandwiches, lunch sandwiches, salads and smoothies. We hope to see you soon!

Hours

Saturday8 AM–3 PM

Customer Reviews

★★★☆☆ 3.0 Elizabeth Campbell · Jan 2026

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 is huge with a lot of empty space/very little decor and bright teal walls that dont give that comfortable coffee shop feeling anymore :( Maybe that’s not so important to others, but it’s something I enjoy for sure!

★☆☆☆☆ 1.0 Rose Cooper · Jan 2026

A friend invited me for coffee saying she was waiting to try the place as she's a recent resident. I was a little late, it was about 2:15 on a weekday. It was empty except for one other table. I made myself a coffee and noticed it was barely above lukewarm. I tried to get the attention of someone but three employees were at the far end of the place near the kitchen, talking and laughing. My friend noticed and came up , got their attention and explained the issue and that I would appreciate a hot cup of coffee. A young woman looked at the cup and said, "there's steam coming out of it" with the most deadpan face resembling a flat tire... I was forced to reiterate that I would appreciate a hot cup of coffee, politely I may add. With a dramatic huff she went to get me the manager/owner Ca

★★★★★ 5.0 joe Wright · Jan 2025

First time here. It is a little different. Walk in to a big room with menus on the wall and things all around you. I chose the Chef’s Salad with a soda. The meal was delicious. I also found the place clean and orderly. I highly recommend this place.

★★★★★ 5.0 Tom Revelle · Sep 2025

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.

★★★★★ 5.0 Stephen Lerch · Aug 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 is always a treat. Highly recommended.

Accessibility & Amenities

✓ Wheelchair Accessible Parking Lot ✓ Wheelchair Accessible Restroom ✓ Wheelchair Accessible Seating

Services

RestaurantCafe

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This listing is informational. Contact the business directly to verify credentials, services, and availability.