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Play it again Sam

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108 S Cross St, Chestertown, MD 21620-1570
08:00 - 15:00
Open now
All hours
Sun 08:00 - 15:00
Mon - Thu 07:00 - 17:00
Fri 07:00 - 22:00
Sat 07:00 - 17:00
More Info
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38 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 38: English reviews
Chestertown, Maryland
Level Contributor
14 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed 7 September 2016

Love going to "Sam's". They are now carrying Rise Up Coffee out of Easton, and it is wonderful. Cozy atmosphere. And the help is very knowledgeable. Especially Tory! Love her. She always asks what I'm in the mood for, and then recommends something. And it is always right-on!!!

Thank Webers2-2016
Washington DC, District of Columbia
Level Contributor
12 reviews
11 restaurant reviews
common_n_restaurant_reviews_1bd8 2 helpful votes
4 of 5 bubbles Reviewed 4 August 2016

This is fun place to meet someone, right in the heart of old Chestertown, and have a breakfast or lunch. It calls itself "Chestertown's Living Room" and that can be true, as almost everyone of one passes through here from time to time. It has an excellent assortment of custom sandwiches, any one of which they will also make as... More 

Thank nealjackson
Chestertown, Maryland
Level Contributor
13 reviews
12 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
4 of 5 bubbles Reviewed 29 July 2016

Often meet a friend for conversation there - and coffee and a bagel or sandwich if its lunch time. Coffee is fine - nice atmosphere - nice couch if you get to snag that. Sandwiches a little pricey, but good.

Thank David R
Level Contributor
108 reviews
77 restaurant reviews
common_n_restaurant_reviews_1bd8 52 helpful votes
1 of 5 bubbles Reviewed 6 December 2015

This place seems to keep a local following, but I wonder why. There is poor flow to the order taking, prep and serving at the counter. Ventilation and overall cleanliness is lacking as well. After a few minutes of watching the mishmash taking place, and not even being acknowledged, I left and went to Evergrain Bread Company down the street.... More 

Thank helios5356
2 reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed 13 October 2015

We met my daughter in law's grandparents there for lunch as they were passing though. The service was great, friendly servers. We went to the counter and ordered then sat until it was ready for pick up. This worked very good for us. Overall I would rate this an excellent stop for lunch while in Chestertown, Md. The food was... More 

Thank Debbie S
Acworth, Georgia
Level Contributor
166 reviews
92 restaurant reviews
common_n_restaurant_reviews_1bd8 49 helpful votes
4 of 5 bubbles Reviewed 27 September 2015

There are places that make you happy to visit and this is one of them. They have survived over the years and offer an honest latte and great lunch sandwiches. They have the local support and I hope that Chestertown never sees the white and green nautical logo!

Thank james h
Chestertown, Maryland
Level Contributor
76 reviews
64 restaurant reviews
common_n_restaurant_reviews_1bd8 10 helpful votes
4 of 5 bubbles Reviewed 26 September 2015

This was the place everyone went to before Evergrain opened. But it is hard to say they are really competitors since the ambiance and food are so different. My friends and I frequent both places, for different reasons. Sam's has some great sandwiches they make on the spot. I love the sausage, egg, and cheese on a bagel for breakfast... More 

Thank plaisaeb
Morristown, New Jersey
Level Contributor
200 reviews
94 restaurant reviews
common_n_restaurant_reviews_1bd8 68 helpful votes
4 of 5 bubbles Reviewed 21 September 2015

A great coffee/sandwich shop, Play It Again Sam's has attractive seating with wi fi for just sitting and enjoying yourself. Inventive sandwiches and a small bakery make meals possible.

Thank Larry D
Level Contributor
14 reviews
9 restaurant reviews
common_n_restaurant_reviews_1bd8 11 helpful votes
3 of 5 bubbles Reviewed 8 September 2015

This place was recommended by a local, but we didn't think the coffee was that great, but it does have a nice feel about it and wi-fi.

Thank SailandSand
Washington DC, District of Columbia
Level Contributor
35 reviews
32 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
4 of 5 bubbles Reviewed 24 August 2015

Great for lunch or breakfast. The Sandwiches are huge and fresh. The Bad A-- had turkey and Swiss and bacon and lettuce and tomato on Panini bread. It was so good my 13 year old had it two days in a row.

Thank bearbranchgirl

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Restaurant Details

Rating summary
  • Food
    3.5 of 5 bubbles
    4 of 5 bubbles
  • Value
    3.5 of 5 bubbles
    3.5 of 5 bubbles
American, Cafe
Breakfast, Lunch, Dinner
Restaurant features
Takeout, Seating
Open Hours
08:00 - 15:00
07:00 - 17:00
07:00 - 17:00
07:00 - 17:00
07:00 - 17:00
07:00 - 22:00
07:00 - 17:00
Location and Contact Information
  • Address: 108 S Cross St, Chestertown, MD 21620-1570
  • Location: United States  >  Maryland (MD)  >  Chestertown

Questions & Answers

Questions? Get answers from Play it again Sam staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?