Play It Again Sam Menu (Update 2025)
Introducing the menu at Play It Again Sam, a delightful destination located at 14 Washington Square, Chestertown, MD. This restaurant offers a cozy atmosphere complemented by exceptional service, making it a dining treasure for both locals and visitors.
The menu features a variety of hearty options that cater to diverse palates. Highlights include the beloved BLT sandwich, renowned for its crispy bacon and fresh ingredients, along with the Chef's Salad, which boasts a satisfying blend of textures and flavors. Breakfast enthusiasts will appreciate that they serve all-day breakfast, including scrumptious bagels and refreshing iced coffee.
With its friendly ambience, attentive staff, and a menu that continuously delights, Play It Again Sam stands out as a must-visit eatery in Chestertown. Whether you’re in for a meal or a quality coffee experience, this spot encourages you to savor every bite!
Coffee (We Serve Rise Up Coffee!)
Coffee Hot
Coffee Iced
Hot Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Latte'
Mocha Latte'
Hot Mocha Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Mocha Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Hot Cappuccino
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Cappuccino
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Cappuccino
Breve Latte
Hot Breve Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Breve Latte
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Tea
Arnold Palmer
Tea
Chai Tea Latte'
Hot Chai
Iced Chai
Hot Matcha
Iced Matcha
Matcha Tea Latte'
Hot Chocolate
Hot Chocolate
Hot Americano
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Americano
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Americano
Red Eye
Hot Red Eye
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Iced Red Eye
Medium - 2 Shots of Espresso. Large - 3 Shots of Espresso.
Lemonade
Orange Juice
Fresh-Squeezed Juice
Arnold Palmer
Arnold Palmer
Smoothie
Fresh Fruit Smoothies
Frozen Drinks
Alaskan (Espresso)
Caramel Mocha (Espresso)
Mint Java
Chai Blizzard
Frozen Hot Chocolate
Frozen Lemonade
Matcha Freeze
BadAss
Turkey, Swiss, Bacon, Avocado, Lettuce & Tomatoes.
BLT & Avocado
Bacon, Lettuce, Tomatoes & Avocado.
BLT
No Avocado & More Bacon.
Hot Roast Beef & Brie
Roast Beef, Brie, Lettuce, Tomatoes, Onions & Horseradish Mayonnaise.
Italian Sandwich
Ham, Salami, Capicola, Provolone, Hot Peppers, Sweet Peppers, Lettuce, Tomatoes, Onions.
Chicken Bacon Ranch & Pepper Jack
Chicken, Bacon, Ranch Dressing & Pepper Jack Cheese.
Chipotle Chicken Sandwich
Chicken, Avocado, Cheddar & Sriracha Mayonnaise.
Chicken Caesar Wrap
Turkey And Swiss
Ham & Cheddar
Ham Swiss & Bacon
Roast Beef & Provolone
Veggie
Hummus, Swiss Cheese, Avocado, Sprouts, Green Peppers, Carrots, Cucumbers, Lettuce, Tomatoes & Onions.
Chicken Salad Sand
Cucumbers. Option to Add Lettuce & Tomatoes.
Tuna Salad Sandwich
Cucumbers. Option to Add Lettuce, Tomatoes & Onions.
Norwegian
Smoked Salmon, Cream Cheese, Capers, Lettuce, Tomatoes & Cucumbers.
PB & J
Sandwiches (We Serve Boar's Head Meats & Cheeses!)
Salads
Chefs Salad
Ham, Turkey, Provolone, Hard-Boiled Egg, Cucumbers, Carrots, Tomatoes, Romaine.
Garden Salad
Avocado, Sprouts, Cucumbers, Carrots, Green Peppers, Tomatoes, Onions, Romaine.
Greek Salad
Feta, Olives, Cucumbers, Green Peppers, Tomatoes, Romaine.
Greek Salad & Chicken
Grilled Chicken Strips, Feta, Olives, Cucumbers, Green Peppers, Tomatoes, Romaine.
Bacon, Egg & Cheese Sandwich
Chicken, Egg & Cheese Sandwich
Egg & Cheese Sandwich
Ham, Egg & Cheese Sandwich
Sausage, Egg & Cheese Sandwich
Veggie Egg & Cheese Sandwich
Breakfast Sandwiches
Breakfast Burritos
Bacon, Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.
Chicken, Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.
Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.
Ham, Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.
Sausage, Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.
Veggie, Egg & Cheese Burrito
A Burrito With Tomatoes, Onions & Sriracha Mayonnaise.