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Welcome to Play It Again Sam

Welcome to Play It Again Sam, a charming eatery located at 14 Washington Square in Chestertown, MD. Known for its warm atmosphere and exceptional service, this restaurant is a local favorite for breakfast, lunch, and coffee. Guests rave about signature dishes like the perfectly balanced BLT sandwich and the delectable chicken salad. The spacious setting allows for a relaxed dining experience, though a casual buzz can be heard as patrons enjoy their meals. With its commitment to quality and community engagement, Play It Again Sam invites diners to savor delightful flavors, making it a must-visit destination in the area.

LOCATIONS

Welcome to Play It Again Sam, a culinary gem nestled at 14 Washington Square, Chestertown, MD 21620. This vibrant eatery has etched itself into the hearts of locals and visitors alike, offering a welcoming atmosphere that sets the stage for delightful dining experiences. Whether you’re searching for a cozy spot for breakfast or a casual lunch, this restaurant has you covered.

From the moment you step inside, you'll be enveloped in a warm ambiance that invites lingering over your meal. The space boasts a unique layout, adorned with menus and a collection of eclectic decor—artifacts that create a lively atmosphere. As Joe Wright, one of the patrons, noted, upon entering, you'll find yourself greeted by cleanliness and order, all contributing to a positive dining experience.

What truly shines at Play It Again Sam is the food. Dishes like the BLT sandwich and chef’s salad have garnered rave reviews from customers like Gianna Boria and Sasi Mahar-Piersma. The BLT is a masterpiece, featuring crispy bacon, fresh greens, and ripe tomatoes, perfectly stacked between toasted bread. The chef's salad, with its variety of textures and flavors, is another standout. For those seeking a satisfying breakfast, the all-day breakfast options, such as flavorful bagels and Rise Up coffee, are sure to please. Deayna Ewell remarked on her delightful breakfast experience, which felt reminiscent of a trendy Atlanta coffee house.

Outstanding service is central to the Play It Again Sam experience. Waitstaff are known for their friendliness and attentiveness, making you feel right at home. One satisfied diner noted that staff remember regulars' orders, a testament to the restaurant’s commitment to building community and connection.

Though the new location is larger, some guests have noted the noise level can get a bit high, as Barbara Cheyney pointed out. Suggestions for enhancing the acoustics have arisen, but this minor inconvenience doesn’t overshadow the overall exceptional dining experience.

In summary, whether you’re a long-time local or just passing through, Play It Again Sam is a must-visit for anyone who appreciates quality food, exceptional service, and a cozy atmosphere. With an array of delightful menu items and a welcoming spirit, it's a place where you can truly savor each moment. I highly recommend trying it out—your taste buds will thank you! With a solid 10/10 from satisfied diners, it’s clear this place is meant to be celebrated.

For reservations or takeout, you can reach them at +1 410-778-2688. Don’t miss out on your chance to visit this friendly local hotspot!

START YOUR REVIEW OF Play It Again Sam
Gianna Boria
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!

joe Wright
joe Wright

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.

Barbara Cheyney
Barbara Cheyney

Great sandwiches, friendly staff. Only been there at new location twice (lunch and breakfast), but will certainly go again. Large space can make it noisy, could use some sound-deadening...maybe some sort of flags hanging from high ceiling?

Sasi Mahar-Piersma
Sasi Mahar-Piersma

I have been going here for years and the service has always been wonderful. Some of the previous employees knew my order by heart when I walked in. The friendly atmosphere was relaxing and the daily "Hi Kiki, your usual?" is something I've really missed since moving away. I absolutely loved the old location and have only been to the new one once but the larger space is definitely nice for both customers and employees.

J Pettitt
J Pettitt

My wife and I eat lunch here a few times a month. The food is good, the service is pretty fast, and I like the atmosphere. I would recommend giving it a try.

Joshua
Joshua

This is by far one of my favorite places to hide away and drink some coffee. I have come here since I was a little kid and always enjoyed this place. The atmosphere is always amazing the people are always welcoming and even the owner is a wonderful woman that holds small talk with customers she really loved her community and it's awesome, As an adult I now come here and have coffee with friends, business associates, and my lovely lady. It's gonna be different when they change locations but maybe the bigger environment will be a good thing and better in the long run I'll just miss the downtown location it was convenient when wanting coffee on the early days like Saturday with the farmers market. Thank you all for a lovely coffee place to enjoy wether it's business or casual I'll always be a customer!

Deayna Ewell
Deayna Ewell

Just left this business and the food and atmosphere was amazing! I love that they have all day breakfast and we were greeted with a big smile and friendly engagement. My daughter and I loved our breakfast bagels, Iced Mocha and Rise Up coffee beverages! Great Spot, you have to try it out!!!! We felt like we were in an Atlanta coffee house!!!

Charish Dean
Charish Dean

Always good food except there is often a wait for your order. Call ahead if in a hurry! I usually order the Badass sandwich and this one was on a bagel. They also serve Rise Up coffee.