A Fun Adventure & Romantic Dinner in Chestertown

Aerial view looking at some of the best things to do in the colonial town of Chestertown, Maryland on the Eastern Shore

It’s never a bad time to retreat to the quiet, picturesque Eastern Shore of Maryland, a seaside destination steeped in history and tradition. That’s especially true when you stay at our Bed and Breakfast on the Eastern Shore, located just outside the town of Rock Hall, MD. Nearby is another great town – Chestertown – a fantastic town steeped in Colonial history and a wonderful place to spend a day. There, you’ll find one of our favorite local restaurants, too – The Kitchen! 

The timeless charm of Chestertown, a Colonial gem surrounded by the sparkling waters of the Chester River, is a picture-perfect place to spend an afternoon. Stroll down its quaint, tree-lined streets, admiring historic brick buildings and centuries-old homes, which all seem to whisper their stories of the past. There are plenty of great things to do in Chestertown, where the vibrant arts scene, charming boutiques, and scenic riverfront invite you in for a quintessential day on the Eastern Shore. 

Explore the town at your own pace, just like you would the rest of the Eastern Shore. However you spend your day in Chestertown, we think there’s only one way to end it – with a fantastic meal at The Kitchen. At The Kitchen in Chestertown, the chefs transform the freshest regional produce and seafood into culinary masterpieces, offering the ideal way to end what’s sure to be a memorable day. The only way to cap off this perfect day is to stay at our top-rated Inn, a short 20 minutes away in Rock Hall. 

Our Bed and Breakfast, with its friendly atmosphere and scenic surroundings, is the perfect complement to your getaway. It will ensure that your time on the Eastern Shore is filled with relaxation, discovery, and enchanting memories. Book your stay with us today! 

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Couple enjoying wine and a great meal at The Kitchen in Chestertown on the Eastern Shore of Maryland

Dine Out at The Kitchen in Chestertown

Dining out on the Eastern Shore of Maryland in the summer is an epicurean delight, particularly for those who relish fresh, locally sourced food. The region is renowned for its Maryland crab, a must-try delicacy served alongside plenty of fresh farm-to-table produce. Dining at local restaurants goes far beyond the food on your plate; it’s an immersion in the region’s culinary traditions and rich heritage. 

There are plenty of great places to eat on the Eastern Shore of Maryland, including a slate of fantastic restaurants in Rock Hall. However, one of our favorite places to send guests is The Kitchen in Chestertown. At The Kitchen at the Imperial in Chestertown, Maryland, this ethos of freshness and local flavors is brought to life in an intimate and welcoming setting. The Kitchen prides itself on a menu that changes with the seasons, ensuring that each dish reflects the freshest, highest-quality ingredients available.

Dining at The Kitchen is an experience that marries simplicity with sophistication—think expertly prepared Maryland crab dishes, succulent seafood, and an array of sides made to pair perfectly. Add flawless service and a cozy and inviting ambiance to an expertly crafted meal, and you truly have the recipe for a fantastic meal. It’s the perfect place to end your day after enjoying all the other great things to do in Chestertown, MD. 

Of course, The Kitchen is one of many great eateries in town. Whether you’re looking for a casual lunch or other choices for dinner during your extended getaway, here are a few different places to consider. 

  1. For refined dining focused on fresh, regional food, another great choice is Watershed. The methods of preparation are traditional, making for a meal that’s memorable and exactly as it was meant to be enjoyed. 
  2. A fantastic lunch spot in Chestertown is Modern Stone Age Kitchen. Like The Kitchen at the Imperial, it focuses on high-quality ingredients and a simple but delicious experience. 
  3. Uncle Charlie’s Bistro, a quaint and casual spot in town, is another excellent choice. The menu is diverse, with something for everyone. 
  4. If you’re in the mood for Italian in Chestertown, Louisa’s is the place to be! This Chestertown restaurant offers a warm, inviting atmosphere and authentic Italian dishes made with fresh, high-quality ingredients.
  5. For fresh seafood on the river, head to The Fish Whistle at the marina. The atmosphere is casual, and you’ll enjoy lovely views of the Chester River, making it a favorite spot on a warm day. 
A sign on the street in town, representing one of the best things to do in Chestertown on the Eastern Shore of Maryaldn

The Best Things to Do in Chestertown Before Dinner

Before you end your day with a dinner at The Kitchen, we hope you spend some time exploring all the other things to do in Chestertown, too. Chestertown is a charming and historic town. It was founded in 1706 and still offers visitors a glimpse into America’s Colonial past. Spend a day here, and you’ll quickly discover the charm and warmth of this historic town.

As you meander through the streets of Chestertown, MD, the rich history and vibrant community spirit become palpable, inviting you to delve into the great things to do here. Enjoy a leisurely stroll along the Chester River, savoring the picturesque views and gentle breezes. Delight in exploring the unique boutiques and art galleries, each offering a glimpse into the creative soul of the town. When hunger strikes, treat yourself to a sumptuous meal at one of the local restaurants, focusing on fresh, locally sourced ingredients that will tantalize your taste buds.

It may seem like just another town on the Eastern Shore, but you’ll soon find not only are there plenty of wonderful things to do in Chestertown, but it’s a town with its own unique character and charm. Whether you’re soaking in the local culture, enjoying the outdoors, or simply relishing the town’s laid-back charm, we hope you take the time to soak up this delightful riverside town. Below, we’ve listed a few of our favorite things to do in Chestertown, MD. 

  1. Visit the Chestertown Farmers’ Market to browse and purchase local produce, crafts, and treats. It’s held every Saturday year-round. 
  2. Take a scenic walk or biker ride on the Wayne Gilchrest Trail (also known as the Chestertown Rail Trail). It’s a scenic ride from the river through the heart of historic Chestertown. 
  3. Take a self-guided historic walking tour of downtown Chestertown. This is a fantastic way to view some of the town’s well-preserved Colonial architecture and one of our favorite things to do in Chestertown, MD. 
  4. The area also has some of the top wineries and breweries on the Eastern Shore, so you can easily couple your visit to Chestertown and The Kitchen with an afternoon visit to a local winery, including Crow Vineyard, one of our favorites. 
  5. Engage with local artists and shop for unique art pieces in the town’s numerous galleries and boutiques.
  6. Take a kayak or canoe trip on the Chester River to experience the area’s natural beauty from the water.


After dinner, it’s time to head back to our relaxing Bed and Breakfast on the Eastern Shore of Maryland—a quintessential Inn on the quiet shores of the Chesapeake Bay. With access to towns like Rock Hall and Chestertown, not to mention all the other fantastic things to do on the Eastern Shore, there’s no better place to unplug this summer. Book your room at our upscale Inn today! 

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