• Story by: Reen Waterman by: Caroline J. Phillips

Bowlingly Estate


Nestled in the heart of the small town of Queenstown, (the original county seat of Queen Anne‘s County in 1707) stands the historic 18th-century Bowlingly estate.

Originally a land patent of 200 acres granted to James Bowling by Lord Baltimore in 1658, Bowlingly was built in 1733 by the estate’s fifth owner, Ernault Hawkins.

Bowlingly is a stately 10,000-square-foot, Flemish-bond, Georgian center hall colonial. Located at the mouth of Queenstown Creek, this private residence is a splendid example of early Maryland plantation architecture.

Positioned atop a high bluff overlooking the entry to the Chester River and modeled after Dutch manor homes, Bowlingly‘s exterior is a masterpiece of symmetry. The perfect placement of doors and windows, along with elaborate brickwork, demonstrate this well.

Bowlingly’s history and architecture position it as a significant landmark. The magnitude of this residence — one of the earliest structures dated on the central Eastern Shore — indicates the prominence of the owner. The undisputed date of building, 1733, is clearly displayed in glazed header brick in the south wall, which now serves as a benchmark against which historians can date other buildings in the area.

During the war of 1812, Queenstown was the only town in the county to be attacked by the British. Before dawn on August 2, 1813, a British raiding party landed and surprised the local militia who were using it for their temporary headquarters. The troops fled and the abandoned estate was thoroughly vandalized and badly damaged by the British. It is rumored that as a result of the attack on the estate, there are cannon balls still embedded in the home’s walls.

This estate has had numerous owners. Most unusual is the Queen Anne’s County Railroad Company, which acquired it in 1897 and converted it into a hotel, adding an amusement park and a race track. This was in the era when steamships plied the Bay, bringing tourists and commerce to our Shores from Baltimore. Back then, “Reaching the Beach” was a circuitous event involving taking a steamship across the Bay and then proceeding by train to the ocean.

Around 1895, Bowlingly became known as “The Ferry House,” due to the influx of tourists who docked at the Queenstown Wharf and stayed in the home. It was in this time period that Bowlingly was painted completely yellow (a color much in vogue at that time). Hotel management further damaged the property by installing 220 feet of covered porch around the house.

In 1900, Bowlingly returned to private ownership. In 1953, the owner, with the aid and advice of architectural historian William Foster, disassembled the remaining sections of the hotel’s porch, removed the yellow paint from the brick walls with muriatic acid, and completed other repairs to bring the home back to its former glory.

Upon entering the home, you are greeted immediately by a double staircase that ascends against the partition walls to a common spacious landing and then continues up a single flight to the second story. According to the National Register of Historic Places Inventory-Nomination Form, the stairway is described as:

“It is an open string stair typical of the period circa 1820-40, with delicately turned newels, square balusters and a simple, continuous ramped walnut rail. The stringers are decorated with scrolled stair brackets and the area below the carriage is finished with flat recessed paneling.”

As you wander through the rooms, floors, and stairwells of Bowlingly, you can easily get lost. Comprised of a main floor, second floor, finished attic, and partially finished basement, this spacious and gracious home boasts seven bedrooms, four full baths, and one half bath. Remodeled several times, it includes elements from at least five different times of construction, one example being the addition of the East-West Wing in 1830.

Rambling through this home you can’t help but admire the gorgeous wood floors and vaulted ceilings. Stepping down three steps into the formal dining room, there are brick tile floors and a view of the white picket-fenced herb garden with boxwood borders and the water. The walls are adorned with artwork dating back to the 18th century.

The ultra-modern kitchen, with commercial-grade appliances, is a gourmet’s delight. On one end of the home is an in-ground pool and pool house. On the other end of the home, an attached caretaker’s cottage.

The latest owners of Bowlingly, Sean and Kellee Glass of Washington, D.C., bought the residence in 2014 as a short sale.

“We were looking for a weekend place, where our young children could run around safely. Living in downtown Washington, D.C., this was not possible. When we found Bowlingly, we fell in love with it,” Kellee Glass said.

When you buy a historic home, in addition to dealing with the historic foundation and its requirements, deferred maintenance can be a challenge.

“When we moved in,” Kellee said, “we didn’t realize the myriad of maintenance issues hidden behind the walls. We have done a great deal of modernizing and updating … it just is not seen in the open.”

The owners take advantage of internet sites, such as Airbnb, to rent their home during selected times during the year.

“It is really nice to share our unique place with other people. Because we have friends and neighbors we care about deeply here, we are very selective of those to whom we choose to rent our home, and we are seeking guests who would treat our home as their very own,” Kellee said.

In addition to renting their home out to weekend guests, the Glasses have received approval from the Queenstown Commissioners to host one large event a month, and several smaller ones.

“Originally this wasn’t something we contemplated. Neighbors kept coming up and asking about holding a wedding or party on our grounds, so in time we decided to pursue this, and are glad we did,” Kellee said.

If you are interested in stepping back in time and experiencing the feel of a bygone era, take advantage of Bowlingly Estate. Whether escaping for rest and leisure, creating a memorable weekend, or celebrating a historic event, consider Bowlingly for your next special occasion.