Known as “The Pearl of the Chesapeake,” Rock Hall, MD, lives up to its name as the ultimate destination for waterfront fun. Excellent restaurants, gorgeous views, and exciting festivals are just the beginning of what you’ll discover here. Take a scenic boat ride along the Chesapeake Bay, dine beside the water, or join in on the Pirate and Wenches festivities. From shopping and dining to tours and events, here are the best things to do in Rock Hall, MD!
Make sure to request access to our free Travel Guide for more recommendations about things to do in Rock Hall, MD. It’s full of information about all of the best places to eat, attractions to see, and events to attend on the Eastern Shore of Maryland.
Top 5 Things to Do in Rock Hall, MD
1. Pirate and Wenches Weekend
Arrrrrg you ready for a weekend of music, mayhem, and merriment? Don’t miss the Pirate and Wenches Weekend in August! This town-wide party features treasure hunts, costume contests, delicious eats, rum tasting, and lively entertainment for all. Come dressed as your favorite pirate and join in the festivities! Then, come back in November for the Sultana Downrigging Festival.
2. Chesapeake Bay Boat Tours
Is there anything more romantic than a sunset cruise along the Chesapeake Bay? When it comes to the best local boat tours, Blue Crab Chesapeake Sailing Charters should be at the top of your list. Climb aboard the 43’ “Island Girl” vessel and sail off into the sunset with your sweetheart. The spectacular views will take your breath away!
From intimate waterfront cafes to fine dining establishments, Rock Hall, MD, restaurants are sure to tantalize your taste buds. Are you craving fresh seafood? Dig into the catch of the day at Pearl on Main. Would you like to grab a quick lunch or coffee? Stop into Java Rock Cafe for signature paninis, gourmet soups and salads, or a piping hot cup of Joe. And if you’d like to enjoy dinner and a view, make a reservation for 98 Cannon Riverfront Grille in Chestertown. With award-winning cuisine and spectacular water views, this may just become your new favorite place to dine!
Whether you’re on the hunt for a fabulous new outfit or searching for unique gifts, you’ll find it all while shopping in Rock Hall, MD. Take your time browsing The Hickory Stick boutique for stylish clothing, nautical gifts, and other coastal delights. Then, stop into Sweet Cheeks Delightful Treats for savory chocolates, cookies, and cupcakes. If you need fishing gear, Hook Line-N-Tackle Shop has a wonderful selection. Not your average bait shop, they also carry a treasure trove of jewelry, gifts, decor, wine, and more.
5. Chestertown Jazz Festival
Held every September, the Chestertown Jazz Festival is another event you won’t want to miss! Get ready to groove at this three-day festival by the water, which features some of the best jazz and blues performances around. The jazz festival takes place across multiple venues, including The Mainstay in Rock Hall and The Garfield Center for the Arts. Make sure to book your tickets and accommodations ahead of time, as they tend to go quickly!
Book Your Stay at Brampton Inn
Now that you know about the best things to do in Rock Hall, MD, it’s time to start planning your trip! If you’re searching for nearby accommodations, we invite you to stay at Brampton Inn. Our enchanting bed and breakfast is convenient to all of these incredible attractions. We’re also located just minutes from all of the best things to do in Chestertown, MD. Wake up to a delicious complimentary breakfast each morning, enjoy romantic strolls through our landscaped gardens, and unwind in your luxurious guest room or cottage.
Experience your getaway to the fullest when you reserve a stay in our Mulberry Cottage. Located at the edge of the woods, this private retreat is an ideal choice for couples. Sink into the luxurious king-sized bed, take a soak in the outdoor Japanese-style tub, or relax beside the fire. This cottage also includes a hammock for two and a large screened porch with serene meadow views. Don’t wait to start planning your getaway to the Eastern Shore of Maryland! Check our availability and book your stay today!