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Best things to do in Chester

Discover the city through the eyes of locals. Find the best things to do, places to eat, and get priceless advice from the people who live here.

Seafood Restaurant
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“$$$$ Award winner: One of best view in America 2019 Come visit them at Kent Narrows!! Live Music Friday and Saturday nights!! Fine Dinning with outdoor seating available. Happy Hour Sunday-Friday!”
12local recommendations
Seafood Restaurant
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“Fisherman's Inn is a family owned restaurant and has been a Maryland Eastern Shore tradition since 1930. Fisherman's Inn specializes in seafood dishes, prime rib, steaks and pasta. The menu features soups, salads, appetizers, traditional fare, casual fare and homemade desserts. Customer favorites include fresh caught Rockfish, Cream of Crab Soup, Oyster Stew, Maryland style Crab Cakes, and Crab Imperial. Guests enjoy the overhead G-scale train running through the dining room along with water views of The Kent Narrows, a beautiful garden, duck pond and newly renovated bar with hot trendy drinks and Happy Hour Monday through Friday from 4-6:30pm. The restaurant also offers private party accommodations for any type of event. Fisherman's Inn is open year round for lunch and dinner 7 days a week, starting at 11 AM *An oldie but a goodie- people travel from all over to eat here on their way to the beach*”
8local recommendations
Thai Restaurant
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“$$$ The food is excellent and consistent. The staff is friendly. This is not a fast food joint. You don't eat and run in 30 minutes. Expect to take some time and enjoy your meal. The decor is upscale but still comfortable.”
7local recommendations
Grocery or Supermarket
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“$5 Fridays and Starbucks coffee shop at Safeway. Food Lion and Safeway are both on the Island.”
4local recommendations
Mexican Restaurant
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“$$ Visit El Jefe Mexican Kitchen/Tequila Bar for fresh Mexican cuisine & tasty Margaritas in a colorful and casual atmosphere. Bienvenidos Amigos! El Jefe Mexican Kitchen is proud to serve quality Mexican food like steak empanadas and mouth-watering tacos. Our dinner menu is filled with authentic dishes like traditional fajitas and delicious tres leches. We’re not a typical restaurant. You get gourmet Mexican food at a very reasonable price. We’ll make you feel right at home in our “casa!””
5local recommendations
Bar
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“Kent Narrows is a beautiful waterfront area. Be sure to check out the seasonal oyster buffet here and the steamed crabs.”
8local recommendations
Bar
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“Island Nightlife. Sun and fun on the water with music and palm trees. See the KIO Nightlife page for details. ”
4local recommendations
Steakhouse
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“Fine Dining on the Eastern Shore and an awesome sports bar for your favorite games. Famous Sunday Brunch and Wine Down Wednesdays. Try the fried chicken!”
3local recommendations
Bar
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“Once a bait shop and now a cool little Tiki Bar! Gotta love it! Biggest little bar on the pier now with an upper deck. Come by bike, car, or boat!”
5local recommendations
Bar
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“Good pub grub in Chester right at the Castle Marina. Monday Open Mic Night. Wednesday Trivia. Weekend Entertainment. Try the calamari, steamed shrimp, and Caesar salad!”
5local recommendations
American Restaurant
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“Now on the Island and only 6 miles from our Kent Island Beach Houses. Homey chain restaurant serving American comfort food, with an on-site general store.”
1local recommendations
Seafood Restaurant
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“Upscale dining on the Kent Narrows waterfront with signature crab cake and soup dishes that you must try. Lunch, Brunch, and Dinner.”
5local recommendations
Brazilian Restaurant
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“Great shrimp and avocado appetizer! Abacate Marajá: Ripe avocado halved and stuffed with shrimp, tomato, cilantro, red onion, green pepper and our cilantro ranch dressing topped with two grilled shrimp.....tried and tested. Also fantastic steak and lamb too!”
3local recommendations
American Restaurant
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“Food + Fun + Beer + Music. Breakfast, Lunch, Dinner, or Happy Hour! See their site for the latest specials but definitely try the $5 Burgers on Sunday evenings, Lobster Mondays, and Prime Rib Tuesdays. and the Copperhead Ale!”
3local recommendations
Donut Shop
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“AARP FREE donut with a coffee. Hang out with the locals for donuts and coffee. ”
1local recommendations
Bakery
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2local recommendations