Where to Eat: The Best Restaurants in Chestertown, Maryland
Chestertown, Maryland, with its charming historic waterfront and vibrant arts scene, offers a delightful culinary journey that reflects both its rich local heritage and the influence of its diverse community. This quaint town, steeped in colonial history, is a canvas of quaint streets lined with culinary treasures, where each meal tells a story of tradition and innovation. As you stroll through the bustling downtown area, the aroma of fresh fare wafts through the air, beckoning food lovers to explore the flavors that Chestertown has to offer.
Start your gastronomic adventure at Casa Carmen Wines, where small plates allow you to savor exquisite Spanish-inspired dishes alongside a refreshing wine flight. With a review raving about the delightful Verde, it’s a perfect spot to unwind after a day of exploration. For a unique brunch experience, head to the Chester River Packet Company, where a delightful buffet complements a scenic boat charter, creating a truly memorable outing. Don't miss Modern Stone Age Kitchen for wholesome and nourishing baked goods that bring comfort and taste, from artisanal pizzas to freshly baked sourdoughs. Finally, stop by Watershed Alley for an unforgettable dining experience featuring fresh, local ingredients in a warm and inviting atmosphere.
Dining in Chestertown is an adventure that invites curiosity and indulgence at every turn. With a mix of cultural influences and local flavors, the food scene is as lively and varied as the town itself. From brunch cruises to cozy eateries, Chestertown promises a feast for both the eyes and the palate, making it a must-visit for food enthusiasts. Discover the stories and flavors behind every dish in Chestertown’s vibrant dining scene—your next favorite spot is just around the corner!
Discover the best restaurants and places to eat in Chestertown, Maryland, near you now.
25 restaurants found in Chestertown.
Find Restaurants in Chestertown Nearby Your Location
Starbucks
Coffee shop
504 Washington Ave, Chestertown, MD 21620
This vibrant coffee haven impresses with expertly crafted beverages, welcoming service, and a light-filled atmosphere perfect for work or relaxation.
Antojitos Norma
Mexican restaurant
840 High St, Chestertown, MD 21620
A delightful food truck serving authentic El Salvadoran and Mexican cuisine, featuring delicious pupusas and traditional tacos!
It’s Masala Time
Indian restaurant
3 Washington Square, Chestertown, MD 21620
Indulge in authentic Indian flavors at this five-star gem, where vibrant spices take center stage in every dish.
Casa Carmen Wines
Winery
312 Cannon St, Chestertown, MD 21620
This cozy vineyard and bar tantalizes with exquisite small plates and exceptional, handcrafted wines like the incredible Espumante.
Chester River Packet Company
Boat tour agency
High Street Town Dock, Chestertown, MD 21620
Experience unforgettable river views while savoring delectable brunch favorites like fresh shrimp and filet sliders! Perfect for groups.
Modern Stone Age Kitchen
Health food restaurant
236 Cannon St, Chestertown, MD 21620
This health-focused eatery captivates with artisan sourdough baked goods and fresh, wholesome meals crafted from scratch daily.
Watershed Alley
Restaurant
337 High St, Chestertown, MD 21620
This top-rated gem serves inventive dishes like lox platters and bison short ribs, showcasing fresh, local ingredients.
Reserve
Procolino's Pizza (Proc’s)
Pizza restaurant
711 Washington Ave #9, Chestertown, MD 21620
Dive into a local favorite where thick crust pizza and fresh fried mushrooms reign supreme in a cozy Italian setting.
Luisa's Cucina Italiana
Italian restaurant
849 Washington Ave, Chestertown, MD 21620
Renowned for exceptional Italian cuisine, this local gem serves delectable pizzas, fresh seafood, and unforgettable chicken piccata!
Stam's Luncheonette
Restaurant
215 High St, Chestertown, MD 21620
Step into a nostalgic lunch counter offering colossal turkey wraps, amazing BLTs, and delectable homemade ice cream!
Phat Daddy's
Barbecue restaurant
205 Spring Ave, Chestertown, MD 21620
Savor mouthwatering barbecue in a relaxed setting, featuring tender ribs, savory pulled pork, and must-try hush puppies!
Reserve
BAD Alfred's Distilling
Restaurant
323 High St, Chestertown, MD 21620
A welcoming distillery and bar serving delicious pizzas, burgers, and standout crab dip, with exceptional, helpful service.
The FREEZE
Restaurant
717 Washington Ave, Chestertown, MD 21620
This cozy spot delights with crispy chicken sandwiches, tasty mac n cheese burgers, and creamy soft serve delights.
Play It Again Sam
Restaurant
108 S Cross St B, Chestertown, MD 21620
This lively café is a haven for coffee lovers, featuring delectable breakfast bagels and signature iced mochas. Enjoy the vibrant atmosphere!
Cafe Sado
Sushi restaurant
870 High St, Chestertown, MD 21620
Nestled in a charming, historic grain mill, this sushi and Thai haven boasts fresh, flavorful dishes like Pad Thai and Beef Penang Curry.
China House
Chinese restaurant
711 Washington Ave #31, Chestertown, MD 21620
A hidden gem, offering innovative vegan dishes like specialty sesame tofu, where attentive chefs ensure memorable dining experiences!
The Kitchen at the Imperial
American restaurant
208 High St, Chestertown, MD 21620
Experience a memorable culinary journey featuring standout dishes like pepper-drizzled chicken salad and exceptional burgers in a delightful courtyard.
Domino's Pizza
Pizza delivery
518 Washington Ave, Chestertown, MD 21620
A friendly pizza joint known for exceptional service, customizable pies, and mouthwatering wings awaits your order!
Reserve
Subway
Sandwich shop
834 High St, Chestertown, MD 21620
This vibrant sandwich shop offers fresh, build-your-own subs like the amazing chicken bacon ranch and classic Philly.
Dunkin'
Coffee shop
715 Washington Ave, Chestertown, MD 21620
This beloved chain boasts friendly service and a tidy atmosphere, perfect for enjoying signature donuts and fresh coffee.
Royal Farms
Convenience store
859 High St, Chestertown, MD 21620
This convenient stop combines a gas station with delicious fried chicken and breakfast sandwiches, perfect for on-the-go cravings.
McDonald's
Fast food restaurant
875 Washington Ave, Chestertown, MD 21620
Timely service and friendly staff create a welcoming atmosphere, serving delicious burgers and fries at a convenient location.
Peak health center
Fast food restaurant
709 Washington Ave, Chestertown, MD 21620
Enjoy wholesome fast food at this health-focused eatery, offering nutritious choices that don't compromise on flavor.