Cruising the Upper Chesapeake

Cruising the Upper Chesapeake

Since we made it Annapolis earlier this year, we wanted to explore further up the Chesapeake. After researching possible destinations in the Upper Chesapeake, we set our sights on Rock Hall, Havre de Grace and possibly going through the Chesapeake and Delaware Canal into the Delaware River.

Havre de Grace, MD is a little town on the western shore of the Upper Chesapeake Bay at the mouth of the Susquehanna River. In 1789, George Washington stayed in town on his way to his first inauguration and the First US Congress was only one vote shy of voting Havre de Grace as the US Capital. There is also a 3-mile loop through town marked by a blue line and sidewalk marking for a self-guided tour that follows General Lafayett’s visit to the town as he was making his farewell tour of the US in 1825. Havre de Grace also lies at the southern point of the Susquehanna/Tidewater Canal which connected to the Pennsylvania Canal which was completed in 1840. We were able to tour The Lock House Museum and see of of the preserved locks along the bank of the river. It was also a primary town on the Eastern route of the Underground Railroad to transport refugee slaves across the river to the free state of Pennsylvania. Havre de Grace is also well known for its duck hunting and local artisans making high quality decoys. 

The historic downtown is made up of 2 local breweries, multiple restaurants, boutiques, and antiques malls. Our favorite shop was Bomboy’s Candy Shoppe which boasts the best salted caramels. We enjoyed both of the Battery Island Brewing Company but Market Street Brewing had a wonderful view over the river and Tidewater Marina. 

We stayed at Penn’s Beach Marina which boasts floating docks, a pool, and large restroom/showers. Even though they did not offer laundry facilities, there was daily yoga offered onsite. This marina is at the mouth of the Susquehanna River which makes for a quicker landing off of the Chesapeake Bay but it is more set up for power boats with shallow drafts and for short term transients. The owners appear to be new to the marina but are very helpful and are making good improvements to the facilities. There is a larger liveaboard and sailing community just further up the river. 

Rock Hall, MD is a charming town on the eastern shore of the Upper Chesapeake Bay. With only a population of less than 2,000, it has a thriving boating community of fishermen, cruisers and boat enthusiasts. There are plenty of food options available in town and along the waterfront, especially on the weekends. We recommend Waterman’s Crab House  which seems to be open most nights of the week and has live music on the patio. The Harbor Shack is also a great waterside hangout with good food and lively locals. We enjoyed having breakfast at Muskrat Alley, but they’re only open on the weekends. Though there is not much in town for shopping, there is a small beach, a grocery store and 3 marine/hardware stores within walking/biking distance from the water. We recommend the Rock Hall Marine Railway for parts as a good alternative to the West Marine in town. We were pretty sad to miss their Pirate Festival earlier in the month due to weather, we enjoyed wandering through the Bike Fest holding a beer and listening to some music. 

We stayed at Rock Hall Landing Marina & Inn, which is one of the marinas closest to town and next door to Waterman’s Crab House and the Rock Hall Marine Railway. To get into the marina, we went through a shallow channel at low tide (not on purpose) which was nerve racking but very doable. The floating docks were well maintained and the dockhands were always on the piers doing maintenance. Their facilities were very clean with a large number of restrooms/showers and free bikes to take around town. Laundry was a small hike across a grass field to their hotel but was totally functional. They also had a pool and a fire pit outside which would be fun to use in the summer. 

We then continued our tour of small towns as we went into the C & D Canal for 2 of our final stops of this trip north, but more on that in the next blog. Skål!

Earth is a small town with many neighborhoods in a very big universe.

Ronald J. Garan, Jr.