Fantastic Chestertown, MD Restaurants on the Eastern Shore

We already know (and celebrate) the many fantastic restaurants in Rock Hall, MD. They do a remarkable job of showcasing the rich seafaring history of this region. But just as magnificent as the town of Rock Hall is our neighboring community of Chestertown, where you’ll find another welcome array of Chestertown, MD restaurants to enjoy. They offer something a bit different than our dining establishments in Rock Hall and are a welcome part of getaways here on the Eastern Shore.

Regardless of where you choose to dine while you’re enjoying a stay at our Rock Hall Bed and Breakfast, you’ll no doubt appreciate the coastal charm of the Eastern Shore. Though it’s just a short drive across the water from major metropolitan areas on the East Coast, it’s quiet and feels tucked away, offering visitors a rich blend of history, culture, and respite. Spend your days biking on rural country roads, walking through the serene landscapes of the Eastern Neck National Wildlife Refuge, or paddling on the quiet waters of the Chesapeake Bay.

In the afternoon, enjoy a wine tasting at one of the Eastern Shore’s many excellent wineries, followed by a sensational seafood-forward dinner at one of our local restaurants. There are, of course, many to choose from. In nearby Chestertown, a delightful destination on the Chester Rit’s just 20 minutes from our Inn, you’ll find a charming historic district to explore. Brick buildings and beautifully preserved homes tell tales of bygone days, and the streets are filled with unique boutiques, art galleries, and views of the river that invite you to slow down and savor the moment.

Speaking of savoring the moment, Chestertown’s exceptional dining scene, like Rock Hall’s, perfectly encapsulates the flavors of Maryland’s Eastern Shore. After enjoying all the charm and cuisine Chestertown, MD restaurants have to offer, return to our welcoming Bed and Breakfast in nearby Rock Hall. With comfortable accommodations and a peaceful setting, we provide the perfect retreat for your Eastern Shore adventure. Make your getaway unforgettable—book your stay with us today!

The Best Chestertown, MD Restaurants

It’s pretty easy to enjoy a great meal while unwinding and enjoying time at our Eastern Shore Bed and Breakfast in Maryland. We’ll start your day off on the perfect note with our gourmet breakfast, and from there, there’s a host of fabulous places to eat in Rock Hall and nearby Chestertown. Depending on where you spend your day, you’ll have the chance to savor the region’s incredible culinary offerings.

From sensational summer crab to delightfully briny winter oysters, there’s no shortage of fresh, locally sourced fare. The food culture on the Eastern Shore is deeply rooted in the Chesapeake Bay and our local watermen traditions. While the area offers an impressive selection of dining options, some of the best meals can be found in Chestertown, MD. Whether you’re wrapping up a day of exploring Chestertown’s historic charm or simply looking for a fantastic dining experience, these restaurants in Chestertown, MD will deliver on all fronts.

Whether you’re craving a casual bite for lunch or looking to explore more refined flavors at dinner, the town’s vibrant restaurant scene has something for everyone. If you’re planning your Eastern Shore getaway, don’t miss the chance to indulge in Chestertown, MD restaurants. We’ve listed a few of our favorites below.

Our favorite among Chestertown, MD Restaurants is The Kitchen at the Imperial. This spot is absolutely worth the 20-minute drive, especially if you’re looking for an elevated meal or a way to mark a special occasion. This spot used to be located in Rock Hall but moved to Chestertown for more space. We’ve been a fan of theirs from the beginning!
For refined dining focused on fresh, regional cuisine, head to Watershed Alley. Like The Kitchen, this is one of the best Chestertown, MD restaurants for an elevated meal or special celebration.
A fantastic lunch spot in Chestertown is Modern Stone Age Kitchen. This establishment focuses on high-quality ingredients that produce a well-rounded but simple experience. The menu items are packed with nutrients, making this an excellent stop for the health-conscious traveler!
If Italian cuisine strikes your fancy, Louisa’s Cucina Italiana is one of the best Chestertown, MD restaurants. The atmosphere is warm and inviting, and the dishes are fresh, authentic, and delicious.
There’s a delicious Oyster & Raw Bar at The Retriever in downtown Chestertown, MD. There’s plenty here on the menu if you aren’t a fan of oysters, and don’t miss one of their exceptional cocktails.
For a meal that’s romantic, casual, and delicious, one of the best Chestertown, MD restaurants is Casa Carmen Wines. It’s a tasting room for this boutique winery that offers an excellent selection of tapas to go along with their wines.

The Best Eastern Shore Bed and Breakfast in Maryland

With so many fantastic Chestertown, MD restaurants to choose from – not to mention those fantastic spots just down the road in Rock Hall – you’re never too far away from a fantastic meal. But let’s not forget the most important meal of the day. Start your day off on the right foot with a delicious, gourmet breakfast at the Inn at Huntingfield Creek. It’s one of the best parts about staying with us at our Eastern Shore Bed and Breakfast in Maryland.

Breakfast is just the start of what makes us a great place to stay on the Eastern Shore, though. Sometimes, the best way to recharge is to find a place where life slows down and the beauty of the Chesapeake Bay takes center stage. That’s exactly what you’ll find at our peaceful Eastern Shore Bed and Breakfast in Rock Hall. No matter the reason for your visit, our Eastern Shore Bed and Breakfast in Maryland offers the perfect combination of comfort, elegance, and relaxation.

Set on 70 acres of scenic countryside near Rock Hall, our property blends coastal sophistication with thoughtful amenities for a getaway you’ll never forget. Choose from guest rooms in the Main House or private cottages, each offering a unique retreat. Spend your afternoons exploring the surrounding area, wandering through our gardens, hanging out by the dock or by the pool, or simply relaxing in the peaceful atmosphere of our Inn.

For those looking to venture out, Rock Hall has no shortage of things to do. Explore the nearby towns of Rock Hall and Chestertown, visit our sacred natural spaces to appreciate all that is the Chesapeake Bay, and fill your stomach with all you can eat of the region’s incredible seafood. Our team is always ready to help you plan your perfect day, complete with personalized recommendations for the best dining, attractions, and more. Whether you’re seeking a quiet weekend escape, celebrating a milestone, or planning a memorable trip with someone special, now’s the time to book your stay at our Eastern Shore Bed and Breakfast in Maryland.