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Play it again Sam

108 S Cross St, Chestertown, MD 21620-1570
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  • Excellent30%
  • Very good47%
  • Average10%
  • Poor5%
  • Terrible7%
2 days ago
“A coffee cafe that's just right!”
4 Aug 2016
“A Funky, Old-style store with Excellent Coffee and Sandwiches”
Closes in 8 min
All hours
American, Cafe
108 S Cross St, Chestertown, MD 21620-1570
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Reviews (40)
Traveller rating
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1 - 10 of 40 reviews

Reviewed 2 days ago via mobile

Small local coffee and sandwich shop, popular with locals and visitors who are not into Dunkin donuts coffee and sweets. Good for breakfast and lunch, including GF bread and some very tasty, locally baked, pre-packaged bakery items.

Thank Rob C
Reviewed 3 weeks ago via mobile

My usual lunch stopover. Like that one can dine in or takeout. Laidback atmosphere. Free WiFi. The best vegetarian sandwich although only offered for a spell.

Thank Lorraine M
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...More

Thank Webers2-2016
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...More

Thank Neal J
Reviewed 30 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
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...More

Thank helios5356
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...More

Thank Debbie S
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...More

Thank james h
Reviewed 27 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...More

Thank plaisaeb
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
Nearby Restaurants
Lemon Leaf Cafe
557 reviews
.12 km away
Blue Heron Cafe
166 reviews
.08 km away
Evergrain Bread Company
133 reviews
.18 km away
Uncle Charlie's Bistro
145 reviews
1.26 km away
Nearby Attractions
Carla Massoni Gallery
17 reviews
.18 km away
Historical Society of Kent County
10 reviews
.22 km away
Garfield Center for the Arts at the Prince Theatre
5 reviews
.17 km away
Chester River Packet Company
45 reviews
.43 km away
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Restaurant Details

Rating summary
  • Food
  • Value
Breakfast, Lunch, Dinner
Restaurant features
Takeout, Seating
Good for
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