Chestertown
Restaurants
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The restaurant is known for its delicious food, including wood-fired pizzas with fresh dough, bubbly cheese, and authentic char. The pulled pork tacos are also a popular choice. The owners are gracious and accommodating, making it a great spot for groups. The Apple Pie Moonshine and burger are highly recommended for future visits.
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The local watering hole! Great food and pool tables.
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Known for having one of the best crab cakes on the Bay.
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Local seafood company.
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Artisan baking, sourced from the best ingredients, made locally in Chestertown, Maryland ... All of Evergrain's bread, pastries and cakes are baked on site.
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Home of the "Big Freeze Burger," Fast Food, Sandwiches, Ice Cream: sundaes, shakes, cones etc. Fried Chicken, Burgers, Steaks, Fries.
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The Kitchen at the Imperial provides an award winning casual fine dining restaurant experience, in a unique, upscale atmosphere. Chef Steve Quigg (winner, Best Chef on the Eastern Shore 3 years in a row) and his staff pride themselves on their farm to table/boat to plate philosophy, making use of the abundant fresh local resources available. The Kitchen staff makes everything in-house, with perfection their aim. Be sure to try the Bloody Mary Brinch on Sundays and the tapas/shared plates menu.
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Serving lunch and dinner daily, featuring Italian specialty entrees, gourmet pizzas and sandwiches in a casual dining atmosphere. Our dishes are prepared with locally grown fresh ingredients. Dine-in or carry out.
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They transform familiar foods such as bread, pizza, cheese, tacos, soups, sandwiches and even cookies into their healthiest versions by using ancestral and traditional approaches to maximize the safety, nutritional value, and flavor.
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PHAT DADDY’S BBQ (PDB) is an award-winning catering company which originated in Glen Burnie, Maryland.
After spending nearly a decade of learning the art of traditional smoked foods PDB acquired a mouthwatering, finger lickin’, down home rub consisting of nine distinct spices to complement a secret cooking sauce and top-notch smoking technique.
After catering countless neighborhood events PDB became a staple in the local community.
In 2021 PDB opened “The Shack” in Chestertown, Maryland. “The Shack” specializes in on-site preparation of meats and pick up & delivery service, in addition to catering of special events.
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Play It Again Sam serves a complete line of coffee offerings, breakfast and lunch specialties, snacks and wine.
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Serving Kent County's favorite pizza and Italian specialties.
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The Shanty Beach Bar is the place to be for live entertainment and our famous mudslides all summer long. Open during the season every Friday, Saturday, and Sunday! The Shanty offers patrons an experience like no other, from casual Friday nights to full concert events featuring National Recording Artists for the Summer Concert Series.
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Chef/owner Brandywine White brings her background as a professional pastry chef to Stam’s Luncheonette. With a passion for pastries, cakes, ice cream, and staples of classic American fare, Brandywine hopes to recreate the delicious treats of generations past as well as the favorite treats of today.
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Ice cream and sweet treat shop.
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The Retriever is a bar featuring oysters and other victuals.
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The menus reflect the long-held commitment of Watershed Alley’s Chef to a combination of fresh ingredients, tasteful simplicity, and beautiful presentations - all inspired by the resources of the Chesapeake Bay watershed.
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Grocery
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Full grocery store.
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Your destination for chocolate and other sweet treats! Enjoy truffles, fudge, fresh roasted nuts, and chocolate delights of all sorts. Plus: Special events, custom chocolate designs, and more.
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Local market. Visit them here.
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Chester River Wine & Cheese Co. is a retail store specializing in wine, cheese, olives, cured meats, pate, and other gourmet specialty provisions. They also offer wine by the glass, cheese and charcuterie boards for onsite consumption.
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A local store that offers locally grown, organic products. This includes their own artesian cheese, butter, and pastured raised beef. Find them online here.
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Full grocery store.
Things to do
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Serving wine and tapas, our Bodega & Tasting Room in downtown Chestertown, MD, is created in the spirit of the traditional wine bodegas of Spain and South America — an unpretentious place to drink well, eat well, and enjoy good company.
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Enjoy a leisurely trip down the Chester River, relaxing on the upper deck or snuggled down in the spacious interior cabin. Food is included!
View their schedule here.
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On Saturday mornings from 8 am to noon beginning about the third Saturday in March and ending about the last Saturday in December, located in beautiful Fountain Park in the heart of downtown Chestertown, on Maryland’s Eastern shore you’ll find wonderful fresh home grown produce, herbs, breads, soaps, plants and cut flowers as well as the hand-crafted works of local artisans.
Visit www.chestertownfarmersmarket.org for more information.
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The Garfield Center is a multi-function community center for the performing arts offering theater, music, film and children's programming throughout the year.
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Enjoy this waterfront winery ideally positioned overlooking the sloping banks of Worton Creek minutes away from the scenic Chesapeake Bay on land steeped in history: originally granted by Cecil Calvert, the 2nd Lord Baltimore, to Lieutenant General Josias Fendall, the 4th proprietary Governor of the Maryland Colony in 1659; subsequently occupied for over a century and a half by 6 generations of one of the founding Quaker families of Kent County; and utilized as a commercial side-wheeler Steam Boat stop post Civil War.
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