Captain Jen’s Treasure Hunt

Exploring Greenbury Point and SOBs

By Jennifer Kaye

The true joy of owning your own seasonal business is when you get to “open” back up for the season. My business involves owning two 74-foot schooners in Annapolis, where we take guests from all over the world sailing on the Chesapeake Bay. So, yeah, I’m busy. When I get busy, I stick to treasure hunting in my own backyard.

Inspirational words at Greenbury Point.

We chose Greenbury Point, a large peninsula with about five miles of trails owned by the Navy. The point offers spectacular views of the Bay, the Annapolis skyline and the Bay Bridge. You may even have seen this area which is clearly defined by three towers that resemble the famous Eiffel in France, but have the added benefit of helping every boater find Annapolis as they make their way up or down the Bay.


In 1649, it was the first Puritan settlement in Maryland and was called Providence. But it was vulnerable to weather–and possible ship attacks–so the settlers moved to what is now Annapolis. In the early 1900s the point became the country’s first Naval Air Station, and had 19 towers to communicate in the two world wars. Around 1999, most of the towers were removed to create a recreational area.


The trails are flat, and there’s lots of high grass for wildlife to hide in. There’s even a Nature Center near one of the trails, known as the Poet’s trail. Here is where we started our hike along a four-mile trail, in the shadow of the three remaining towers, in search of four geocaches.

La Tour Eiffel in Annapolis.


As we went after the first cache along Carr’s Creek, all we could hear was the chirping and singing of birds. The spring wildflowers were in full bloom and we came across some amazing picnic spots and even a rope swing. I don’t know if I would be using that, but it looks like fun. A couple of miles on we found ourselves under a towers built around 1913. Surreal to think that this tower has stood here for more than a century!


We then walked along the Bay where every 300 feet you can take a side path to sit near the water. The ospreys sounded like they were in a squabble. We found another cache right an overlook of the Bay Bridge.


And then we came to an area of stone rubble. This was a puzzle cache that required us to do some math and projections to complete an online puzzle. The rubble was actually the crest from Isherwood Hall, home of the Naval Academy’s engineering department from 1905 to 1975. When the building was demolished, according to the info on the geocaching website, one crest was used as part of new construction while the other was placed on Greenbury Point until further notice. So along with our geo-caching find, we got to discover a little history. Ex Scientia Tridens!

Now, where to go for a little refreshment? We settled on my favorite place for a relaxed Sunday afternoon of local oysters and beer. Sailor Oyster Bar, or also known as SOB, has a Sunday special of buck-a-shuck oysters, local (20 oz) draft beers for four bucks, and specials on wine and the cocktail of the day. The brewery RAR makes the signature SOB’s Cream Ale, a perfect pairing with Chesapeake Bay Oysters and homemade hot sauce that comes in a container that looks like an eye dropper container. The beer is on nitro, which brings out the creaminess and spring-like floral hops that you smell more than you taste.

Three notes about Sailor Oyster Bar: staff is awesome, restrooms are playful (go see for yourself), and the food is done with no kitchen except for a toaster and a blow torch. So think crudo, tinned fish, cured meats, cheese and salads and sandwiches. You won’t find crabcakes here which is sometimes a welcome sign for locals.

Reader Interactions

Latest Issue

Categories