Waterfront Destinations Around the Chesapeake Bay Dockshare’s Top 10 Suggestions

1. Pier450 – Once known as Scheibel’s Fish Camp, this beloved spot has been reimagined into a stylish waterfront restaurant. Pier450 specializes in casual fine dining with a relaxed nautical vibe and unbeatable summer sunsets. Though it opened in 2019, it’s already a favorite among locals. Be sure to call ahead for weekend reservations!
   
2. Dobbin’s Island – This tiny island is a hotspot for summer fun. With its open beach, frequent raft-ups, and calm waters perfect for swimming, it’s an ideal place to anchor, enjoy a packed lunch, and kick back. Tip: Dobbin’s Island is privately owned, so be sure to respect posted boundaries and access guidelines.  
3. Haven Harbor Marina Resorts – This marina in Rock Hall is a great place to stop for drinks in their resort-style lounge and bar. They have a primary location at Haven Harbor with an Inn and slip services for anyone looking to get away on the Chesapeake. 
4. Downtown Annapolis – A Chesapeake Bay classic and historic waterfront town, downtown Annapolis offers activities to fill a day or even weekend for just you or the entire family. Immediately off the boat, you find yourself in the heart of Maryland’s capital city where you can enjoy seafood restaurants, ice cream shops and dessert cafes, boutiques and shops, and attractions and museums. Downtown is only a short walk to the national Naval Academy – a must see for Annapolis visitors. 
5. Waterman’s Crab House – Right on the shores of Rock Hall, sits Chesapeake Bay Magazine’s 2019 “Best Crab House”. This place is everything you want in a crab house- serving delicious seafood and staying true to a maritime atmosphere. They even offer live entertainment on most summer nights.
6. Baltimore Inner Harbor – Dockshare was born out of Baltimore and it is no surprise that we love the harbor! After a fun boat ride, stopping in the Inner Harbor has endless possibilities. Walk the promenade and enjoy waterfront experiences, check out many of Baltimore’s finest attractions, and dine at one of the destination restaurants. Load up the family and head to the Inner Harbor for a fun-packed day trip to explore downtown Baltimore!
7. Sandlot – Baltimore While checking out the Inner Harbor, our top pick restaurant is Sandlot. It’s more than just a bar and restaurant- it’s an oasis of activity including volleyball, cornhole, swings, picnic options, and great views of Baltimore’s skyline. Located right in the heart of the Inner Harbor, Sandlot is an experience everyone can enjoy after a day on the water. Be sure to visit soon – the Sandlot is occupying its final season in this location. 
8. St. Michael’s – This sweet waterfront town has many attractions to enjoy. Home to the Inn at Perry Cabin, great shopping, fine dining, and Chesapeake Bay history, St Michael’s is a great stop to share with friends and family. 
9. The Jetty – This restaurant is a local favorite on the Eastern Shore. Located in Kent Narrows, this waterfront restaurant and bar has a great fresh menu and even better views. The Jetty has great nighttime lighting and a lively atmosphere for all times of the day.
10. Hemingway’s Restaurant – Hemingway’s Restaurant in Stevensville has a fun and sophisticated ambiance  The perfect waterfront lookout and great menu leaves guests satisfied and coming back for more. Be sure to add this stop on your list for your next tour of the Chesapeake.  

We’ve shared some of our favorites, now it’s your turn to get out and explore these waterfront destinations along the Chesapeake Bay. Remember, parking your boat or watercraft can be difficult at busy waterfront destinations. Don’t get discouraged — Check out Dockshare to make parking a breeze while making your summer stop that much easier.

Visit us next month as we share some additional Chesapeake Bay destination favorites.