Taste Excellence at the Best Restaurants on the Eastern Shore of MD

Where you decide to eat during a vacation can make or break your day. Luckily, we already sorted through the possibilities and picked out the best options for you to enjoy. Whether you are planning a romantic dinner on the waterfront or a casual night out with the family, we have got you covered. Discover the best restaurants on the Eastern Shore of MD and get one step closer to a full stomach. You can even plan the ultimate foodie getaway by booking one of our beautiful vacation rentals near your favorite eateries!

The Top Restaurants on the Eastern Shore of MD


Interactive Restaurant Guide

If you are not sure where to start or have not chosen your ideal destination yet, we invite you to check out our interactive guide. It provides a complete, convenient overview of all the best Eastern Shore restaurants. You can view a map, find addresses, look at reviews, and even get a sneak preview of what each restaurant looks like. Or, feel free to scroll down for more detailed recommendations on the top spots for each community.

St. Michaels Restaurants

St. Michaels is home to gorgeous scenery, beautiful homes, and historic streets, making it one of the most sought-after destinations for peaceful retreats. You can expect the restaurants to be equally impressive! All you need to do is take one bite of the cuisines here to see what we mean. Whether you are craving pizza, seafood, or steak, you can find it all in St. Michaels. It is also home to some of our favorite waterfront restaurants on the Eastern Shore of MD!

Easton Restaurants

There are also several restaurants in Easton, MD, awaiting you a little further inland. From cozy cafes to elegant dining areas, there is something for everyone here. You can grab a quick burger, enjoy specialty salads, and even fill your stomach with award-winning barbecue in a casual atmosphere. Of course, Easton is also home to a variety of fine dining restaurants on the Eastern Shore of MD. Take a look and plan an intimate evening with your special someone!

Cambridge Restaurants

Cambridge, Maryland, is a destination in itself. So, of course, it has several fantastic places to eat! There are fresh seafood spots, eclectic bistros, and everything in between for all palates and cravings. Discover the possibilities and remember to stop in at the charming shops throughout the downtown area, too! There is always plenty of time to treat your taste buds and pick up a unique souvenir from your visit as well. Or, grab a gift for your friends and family!

Oxford Restaurants

This small town is perfect for low-key, relaxing getaways. However, you are still going to work up an appetite, and we know a few dining establishments that will make you hungry just thinking about them. Explore the options and check out your favorites as you stroll through town. Their friendly, inviting atmospheres will help you maintain those casual vacation vibes.

Tilghman Island Restaurants

Tilghman Island is a quiet stretch of land known for fishing, boating, and a wealth of unspoiled natural beauty. We highly recommend trying the seafood here. It is a great way to refuel and relax after your adventures on the water! Many of the popular seafood restaurants are on the waterfront so you can pair your crab cakes and rockfish with gorgeous views. It may be a small, coastal village that is only three miles long, but you can still find multiple top-notch restaurants here.

Chestertown Restaurants

You may have heard of the quaint, charming atmosphere in Chestertown, but do you know about all the great restaurants it has in store for you? This area is home to local farms and vineyards, making it perfect for businesses to implement farm-to-table practices. Best of all, you get to taste all the fresh flavors and seasonal ingredients for yourself! It does not get much better than that.