Play It Again Sam
$ • Coffee Shops, Juice Bars & Smoothies
Hours:
108 S Cross St B, Chestertown
(410) 778-2688
About Play It Again Sam
Customers' Favorites
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
Play It Again Sam Reviews
Ratings
Menu
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Hours
| Monday | 7AM - 3PM |
| Tuesday | 7AM - 3PM |
| Wednesday | 7AM - 3PM |
| Thursday | 7AM - 3PM |
| Friday | 7AM - 3PM |
| Saturday | 7AM - 3PM |
| Sunday | 8AM - 3PM |
Play It Again Sam is a popular restaurant in Chestertown that offers a variety of sandwiches, including the well-loved Badass sandwich. The atmosphere is friendly and inviting, with both outdoor and indoor seating that tends to be busy, especially on Sundays when Washington College is in session, making some wait times likely. The staff is welcoming and attentive, providing excellent service. The music playlist features classic artists like The Stones, Blondie, and Bowie, creating a nostalgic vibe. Vegetarian options are available, and the staff is happy to modify dishes to meet dietary needs. Recently, customers have noted that the new location feels less cozy and more loud and corporate, lacking the charm and personality of the old spot. The space is echoey and noisy, making it hard to hear yourself talk, and the decor is minimal with no art, books, or board games. Despite these changes, many still find the team friendly, the menu fairly priced, and the food good with generous portions. The atmosphere and food quality make it a place worth visiting, whether for dine-in or takeout.