Sometimes the fantastic food is the real reason you visit Maryland’s Eastern shore, and all of the fun outdoor activities are just icing on the crab cake! The area around our waterfront Inn offers such a wide variety of locally sourced and professionally crafted cuisine and libations that you’re certain to find a new favorite. We hope this list will help you plan your next epicurean excursion near our Chesapeake Bay Inn. Keep scrolling to see a few of our favorite “must-taste” establishments, including premier restaurants, a winery and a even a local distillery.
Go Wine Tasting at an Award-Winning Winery
To prime your palate, plan a trip to Crow Vineyard and Farm, just a short drive from our romantic Maryland B&B. In their tasting room you’ll be able to sample delectable wines which showcase the area’s unique soil, climate and terroir. If you have the time, we suggest that you tour the 365 acre farm or plan ahead to attend one of their fun events or winemaking seminars to learn more about the premium award-winning wines. They are open every day from noon-5pm, except holidays, and are waiting to welcome you with their gracious hospitality to their authentic farm.
Enjoy Maryland’s Bounty with a View of the Bay
For lunch or dinner, we can’t recommend Barbara’s on the Bay enough. This waterfront gem is a true passion project of Barbara herself, who gave up her status as a lauded chef in New York City to run this warm and friendly restaurant overlooking the Bay. We suggest you start off your meal with their signature house-made Bloody Mary and their Scotch Eggs or Crab Pretzel, then move on to the Oysters. The Raw Oysters are always good, but the Grilled Oysters are to die for! To make this great dining experience even better, take a walk on pristine Betterton Beach, just steps from Barbara’s fantastic restaurant. Check their hours before you go because they change seasonally.
Drink and Dine at a Delightful Micro Distillery
If you’re looking for a reason to venture into Chestertown proper, then Bad Alfred’s is reason enough. We often wonder why it’s named “Bad” when it’s oh-so-GOOD! This casual restaurant serves wood-fired pizza and pub food which is always excellent. When you pair that with a cocktail made with their locally distilled Brandy, Rye, or Gin it becomes a party in your mouth. They usually have one or two stills running every weekend so you can get a glimpse of how their high quality spirits are made – you might even call it an educational outing! Just note that they are closed on Tuesdays, and only serve drinks on Sundays.
Experience “The Best of” Dining in Chestertown, MD
To get a true taste of all of the goodness that Maryland’s Eastern shore provides, take your dining experience to the next level at The Kitchen at the Imperial. This fine dining restaurant with a casual feel serves farm-to-table and ocean-to-table cuisine, with a menu that changes weekly or daily based on the best available ingredients. This philosophy has led to so many “Best of” awards that we’ve lost count. Whether you are celebrating a special occasion or just want to experience the most mouthwatering food our area has to offer, book your table now for lunch, dinner or their famed Bloody Mary brunch!
Stay Near it All at Our Luxury Waterfront Inn
If going out is just too much effort when you visit our romantic waterfront Bed and Breakfast, don’t worry, you won’t go hungry. Your day will start with a delicious full gourmet breakfast included with your night’s stay. For a light snack, you’re welcome to peruse our complimentary Guest Pantry featuring a variety of healthy snacks and our signature, freshly baked, oatmeal cookies. If you need more of a meal, then you can order our festive Crab Feast, which is available seasonally April through October. Or during the colder months, November through March, we offer our Soup-er Supper to keep you warm and cozy. And as always, every Friday we have our Manager’s Wine and Cheese Hour to look forward to! So come visit our foodie-friendly B&B near Chestertown, MD for a getaway to the Eastern Shore that you won’t soon forget. Just choose your favorite room and we’ll have a warm welcome ready for you when you arrive, and even a cheese plate if you desire! Bon Appétit!Book Now