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

Summer boating season is our favorite timeof the year because of the many waterfront destinations around the Chesapeake Bay. A good boat ride never gets old, and  a day trip on the water can get even better when you make stops along the way. The perfect little waterfront  restaurant, marina, or local beach can make your trip that much more enjoyable and memorable. Here are Dockshare’s top 10 picks for a day on the Chesapeake Bay.

Top 10 Chesapeake Bay Waterfront Destinations 

  1. Pier450 – This beloved spot in St. Mary’s County was once “Scheibel’s Fish Camp” and has since been transformed into a waterfront restaurant stop. Specializing in casual fine dining, Pier450 provides a comfortable natical atmosphere, and amazing summer sunsets. Though the restaurant was just recently launched in 2019, it is already a big hit among the locals. Be sure to call ahead and schedule a reservation for weekend visits.
  2. Dobbin’s Island – Located on the Magothy River, Dobbin’s Island is always bustling with activity. This tiny island has an open beach for visitors, near constant raft-ups, and summer swimming. It’s a great place to drop the anchor, eat your packed lunch, and just hang out! Tip: Because it is privately owned, be sure to respect the boundaries for public visitation.  
  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.