Chestertown Restaurant Guide

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  Luisa's Cafe ($$)
  

  Italian, Bar, Seafood • Menu Available

  14 Washington Sq, Chestertown, MD
  (410) 778-5360 (410) 778-5360

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  Uncle Charlie's Bistro ($$)
  

  American, Sandwiches, Chicken, Wings • Menu Available

  805 High St, Chestertown, MD
  (410) 778-3663 (410) 778-3663

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  Evergrain Bread Company ($$)
  

  Bakery, Breakfast, Coffee Shop • Menu Available

  203 High St, Chestertown, MD
  (410) 778-3333 (410) 778-3333

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  Cafe Sado ($$)
  

  Japanese, Sushi, Thai • Menu Available

  870 High St, Chestertown, MD
  (443) 282-0148 (443) 282-0148

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• 
  Procolino Pizza & Italian ($)
  

  Pizza, Italian • Menu Available

  711 Washington Ave # 9, Chestertown, MD
  (410) 778-5900 (410) 778-5900

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  Play It Again Sam ($)
  

  American, Coffee Shop • Menu Available

  108 S Cross St, Chestertown, MD
  (410) 778-2688 (410) 778-2688

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  Chester River Wine & Cheese ($$)
  

  Wine Bar • Menu Available

  117 S Cross St, Chestertown, MD
  (443) 282-0220 (443) 282-0220

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  The Imperial Hotel ($$)
  

  Breakfast, Brunch, Buffet, Diner, Tapas • Menu Available

  208 High St, Chestertown, MD
  (410) 778-5000 (410) 778-5000

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  Molly Mason's ($)
  

  American, Burgers, Barbecue • Menu Available

  12503 Augustine Herman Hwy, Chestertown, MD
  (410) 348-2430 (410) 348-2430

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  The Freeze ($)
  

  Fast Food • Menu Available

  713 Washington Ave, Chestertown, MD
  (410) 778-2128 (410) 778-2128

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• 
  China House ($)
  

  Chinese • Menu Available

  711 Washington Ave # 31, Chestertown, MD
  (410) 778-3939 (410) 778-3939

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  Subway Sandwiches & Salads ($)
  

  Subs, Wraps, Salads, Breakfast, Catering • Menu Available

  111 Elm St, Chestertown, MD
  (410) 850-4950 (410) 850-4950

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• 
  Watershed ($$)
  

  Seafood • Menu Available

  337 High St, Chestertown, MD
  (443) 282-9797 (443) 282-9797

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  98 Cannon Riverfront Grille ($$)
  

  Seafood, Burgers, Bar • Menu Available

  98 Cannon St, Chestertown, MD
  (443) 282-0055 (443) 282-0055

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  Milano's Pizzeria ($$)
  

  Pizza • Menu Available

  6346 Church Hill Rd, Chestertown, MD
  (410) 810-1300 (410) 810-1300

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  Blue Bird Tavern ($)
  

  American, Bar Food, Sandwiches, Subs • Menu Available

  512 Washington Ave, Chestertown, MD
  (410) 778-2885 (410) 778-2885

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• 
  McDonald's ($)
  

  Burgers, Breakfast, Fast Food • Menu Available

  875 Washington Ave, Chestertown, MD
  (410) 810-0163 (410) 810-0163

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• 
  Casa Carmen Wines ($$)
  

  Tapas • Menu Available

  312 Cannon St, Chestertown, MD
  (410) 390-9921 (410) 390-9921

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• 
  Figg's Ordinary ($)
  

  Breakfast, Brunch, Gluten-Free, Desserts • Menu Available

  207 South Cross St, Chestertown, MD
  (410) 693-1883 (410) 693-1883

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• 
  Dunkin' ($)
  

  Donuts, Breakfast, Coffee Shop • Menu Available

  315 High St # 100, Chestertown, MD
  (410) 778-6211 (410) 778-6211

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  Taco Bell ($)
  

  Mexican, Fast Food, Tacos • Menu Available

  709 Washington Ave, Chestertown, MD
  (410) 810-1399 (410) 810-1399

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• 
  Papa Smurfs BBQ Food Truck ($)
  

  Food Trucks, American, Barbecue • Menu Available

  848 High St, Chestertown, MD
  (410) 758-7666 (410) 758-7666

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• 
  Germaine's ($)
  

  Crepes, Sandwiches • Menu Available

  827 High St, Chestertown, MD
  (443) 282-0048 (443) 282-0048

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• 
  Happy Chicken Bakery ($$)
  

  Desserts, Breakfast, Brunch • Menu Available

  215 Scheeler Rd, Chestertown, MD
  (443) 988-3955 (443) 988-3955

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• 
  Phat Daddy's BBQ Shack ($$)
  

  Barbecue, Southern, Hot Dogs • Menu Available

  205 Spring Ave, Chestertown, MD
  (443) 282-0028 (443) 282-0028

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• 
  Prickly Pickle ($)
  

  Salads, Burgers, Sandwiches • Menu Available

  827 High St, Chestertown, MD
  (443) 282-0078 (443) 282-0078

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• 
  Arby's ($)
  

  Sandwiches, Chicken, Salads, Fast Food • Menu Available

  707 Washington Ave, Chestertown, MD
  (410) 810-8955 (410) 810-8955

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  Great Oak Landing Lodge ($$)
  

  American • Menu Available

  22170 Great Oak Landing Rd, Chestertown, MD
  (410) 778-2100 (410) 778-2100

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• 
  Apos Pizzeria ($$)
  

  Pizza • Menu Available

  6520 Church Hill Rd, Chestertown, MD
  (410) 778-3737 (410) 778-3737

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  Modern Stone Age Kitchen ($)
  

  Breakfast, Brunch, Pizza, Deli • Menu Available

  236 Cannon St, Chestertown, MD
  (410) 996-4776 (410) 996-4776

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• 
  Domino's Pizza ($)
  

  Pizza, Subs, Pasta, Wings • Menu Available

  518 Washington Ave, Chestertown, MD
  (410) 810-3811 (410) 810-3811

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• 
  Stam's Luncheonette ($)
  

  Ice Cream, Yogurt, American • Menu Available

  215 High St, Chestertown, MD
  (410) 885-6722 (410) 885-6722

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• 
  KFC ($)
  

  Chicken, Fast Food • Menu Available

  709 Washington Ave, Chestertown, MD
  (410) 810-1399 (410) 810-1399

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• 
  Subway Sandwiches & Salads ($)
  

  Subs, Wraps, Salads, Breakfast, Catering • Menu Available

  834 High St, Chestertown, MD
  (410) 778-5388 (410) 778-5388

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• 
  Farmers Table ($)
  

  American, Breakfast, Brunch • Menu Available

  11 Washington Sq, Chestertown, MD
  (443) 282-0008 (443) 282-0008

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• 
  The Channel Restaurant ($$$)
  

  Seafood • Menu Available

  21085 Tolchester Beach Rd, Chestertown, MD
  (410) 778-1400 (410) 778-1400

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  Mamma Mia ($$)
  

  Italian, Pizza • Menu Available

  6520 Church Hill Rd, Chestertown, MD
  (410) 810-3000 (410) 810-3000

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  Billy's Crabs ($$)
  

  American, Seafood • Menu Available

  1605 Mcginnes Rd, Chestertown, MD
  (410) 778-3511 (410) 778-3511

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• 
  C Town Deli ($)
  

  Deli, Sandwiches, American • Menu Available

  511 Washington Ave, Chestertown, MD
  (410) 778-3119 (410) 778-3119

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• 
  Shoreman Pit Beef ($)
  

  Barbecue, Burgers, Sandwiches • Menu Available

  Chestertown, Chestertown, MD
  (410) 778-2333 (410) 778-2333

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• 
  Chestertown Farmers Market ($)
  

  Farmers Market • Menu Available

  Chestertown, Chestertown, MD
  (410) 639-7217 (410) 639-7217

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• 
  Papasmurf BBQ ($$)
  

  Barbecue • Menu Available

  101 Camelot Dr, Chestertown, MD
  (301) 395-4353 (301) 395-4353

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  Dunkin' ($)
  

  Donuts, Breakfast, Coffee Shop • Menu Available

  715 Washington Ave, Chestertown, MD
  (410) 224-3117 (410) 224-3117

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• 
  Downey's ($$)
  

  American

  713 Washington Ave, Chestertown, MD
  (410) 778-2128 (410) 778-2128

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• 
  Fish Whistle ($$) - Closed
  

  Barbecue, Burgers, Sandwiches, Subs, Seafood • Menu Available

  98 cannon St, Chestertown, MD
  (410) 778-3566 (410) 778-3566

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• 
  Andy's ($$) - Closed
  

  American • Menu Available

  337 High St, Chestertown, MD
  (410) 778-6779 (410) 778-6779

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• 
  Black Eyed Susan Restaurant ($$) - Closed
  

  American • Menu Available

  601 Washington Ave, Chestertown, MD
  (410) 778-1214 (410) 778-1214

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• 
  Blue Heron Cafe ($$$) - Closed
  

  Seafood, American New • Menu Available

  236 Cannon St, Chestertown, MD
  (410) 778-0188 (410) 778-0188

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• 
  Ellen's Coffee Shop & Family ($) - Closed
  

  Coffee Shop, Breakfast, Brunch, American • Menu Available

  205 Spring Ave, Chestertown, MD
  (410) 810-1992 (410) 810-1992

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• 
  Harbor House Restaurant ($$) - Closed
  

  American • Menu Available

  23145 Buck Neck Rd, Chestertown, MD
  (410) 778-0669 (410) 778-0669

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