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Maryland Eastern Shore › Maryland Eastern Shore › Chestertown

Best Restaurants in Chestertown

2 restaurants analyzed · Maryland Eastern Shore

Chestertown is known for American, Mediterranean dining, with 2 top-rated restaurants.

Restaurants

• Brampton 1860 A+ · Bed and breakfast with an on-site dining program, Inn
• Luisa's Cucina Italiana A- · Italian restaurant, Full-service dining

Areas within Chestertown

• Heron Point

Top Cuisines

• American — 1 restaurants
• Mediterranean — 1 restaurants

Find Your Next Meal in Chestertown

• Casual Meal restaurants in Chestertown — Quick, quality, no fuss
• Date Night restaurants in Chestertown — Romantic dining for two
• Fun with Friends restaurants in Chestertown — Something everyone will enjoy
• Family Outing restaurants in Chestertown — Kid-friendly, stress-free dining
• Solo Dining restaurants in Chestertown — Comfortable spots for dining alone
• Business Discussion restaurants in Chestertown — Professional setting, no distractions
• Vegetarian-Friendly restaurants in Chestertown
• Vegan-Friendly restaurants in Chestertown
• Gluten-Free Friendly restaurants in Chestertown
• Walk-ins Welcome restaurants in Chestertown
• Highly Authentic restaurants in Chestertown
• Local Favorites restaurants in Chestertown
• Easy Parking restaurants in Chestertown
• Amazing Setting restaurants in Chestertown
• Hidden Gems restaurants in Chestertown
• Great Value restaurants in Chestertown

Early reads

Preliminary reads are early assessments from a smaller review sample, not full Seemor analyses.

• Procolino's Pizza B-range · Preliminary

  This is an informal, busy local institution with slices on display, quick counter ordering, and a welcoming owner-led atmosphere. Most reviewers praise the pizza and broad Italian-American menu, though a minority report greasy, undercooked, or disappointing dishes. Try: pizza by the slice.

• Milano's Pizzeria and Grill B-range · Preliminary

  This is a casual, community-minded pizzeria and grill with warm staff, quick service, and a generally inviting atmosphere. Pizza and cheesesteaks are the clear strengths, though delivery and order accuracy have drawn some serious complaints over time. Try: pizza.

• Cafe Sado Chestertown B-range · Preliminary

  This tucked-away restaurant pairs a handsome converted-mill setting with lively sushi and Thai cooking, especially when the kitchen is on form. Sushi and value deals are the safest bets; some cooked dishes and takeout orders have drawn serious quality and execution complaints. Try: Sushi rolls.

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