St. Anne’s Church sits at the top of West Street in Annapolis, MD. Photo courtesy of the author.

West Street, one of the gateways into Annapolis is lined with a variety of  buildings, many of them rich with historical significance. Let’s take a look at one of the oldest streets in America like an artist would a canvas, with a quick thumb nail sketch of West Street’s most prominent architecture!

St. Anne’s Episcopal Church

Church Circle

At the terminus of West Street located proudly in the center of Church Circle stands historic St. Anne’s Episcopal Church. It was founded in 1692 after the passage of the Establishment Act, which also allowed for the construction of the State House. The existing church is the third one on the property. The first, built in 1704 was was razed in 1775 to allow for the erection of a larger structure. In 1858 on Valentine’s Day eve, a fire destroyed the second church. That building was replaced a year later with the present church, a landmark in the Romanesque-Revival style, popular for churches in the 1840-50s. Striking interior features include dark wooden beams, Tiffany windows, as well as the stone altar and the font produced by Maryland sculptor, William Henry Rinehart. The tower which houses the town clock, included by request of the City of Annapolis was completed in 1865.

St. Anne’s Church occupies the circular piece of land at Church Circle and West Street. Photo courtesy of the author.

Ram’s Head Tavern

33 West Street

Rams Head Tavern, family owned and operated since 1989, is the culmination of many expansions, beginning as a small pub. Back then, when I worked at the Arundel Center it was often a choice for lunch. I recall accessing the dimly lit eating and bar area down a few steps, below street level.

The lower bar at Rams Head Tavern retains much of it’s colonial charm. Photo courtesy of the author.

Rams Head is the combination of several buildings, constructed in the 1770s and into the 1800s. Research indicates the spaces were used for various commercial purposes, but operated as taverns for the majority of the time. The property was once owned by St. Anne’s Parish and leased to William Reynolds, a hatter and dry goods salesman, and namesake of Reynolds Tavern, located around the corner on Church Circle.

There are a couple of ghost stories associated with Rams Head that have garnered attention over the years. One such story is attributed to a mischievous spirit named Amy. The story goes, Amy enjoys flirting with the male customers and often plays pranks on female employees  and customers. The other haunting spirit is said to be a soldier, who has been spotted in uniform wandering in the hallways.

The property was once owned by St. Anne’s Parish and leased to William Reynolds, a hatter and dry goods salesman, and namesake of Reynolds Tavern, located around the corner on Church Circle. Photo courtesy of the author.

Visitors Center

26 West Street

Have you noticed the deep blue building with bright red double doors located in the first block of West Street? It’s the Annapolis Visitors Center, the place with everything needed to guide your visit to the city and the surrounding areas.


The Visitor’s Center was originally built by Charles Carroll. Photo courtesy of the author.

This 2.5 story structure was originally built as a dwelling by Charles Carroll, grandfather of Charles Carroll of Carrollton, signer of the Declaration of Independence. However, ownership changed many times over the years. Under the possession of the widow of Reverdy Ghiselin in 1784, rooms were available to rent to those passing through town. Legislators such as Thomas Jefferson and James Monroe, delegates from Virginia to the Continental Congress at the time, were among the many boarders who would rent a room for their stay in Annapolis.

Forefathers such as Thomas Jefferson and James Monroe, delegates from Virginia to the Continental Congress, rented rooms here on their visit to Annapolis. Photo courtesy of the author.

Later, the house reverted to use as a single family dwelling by various owners in the 1800s.  In the early 1900s, it was converted to commercial usage with alterations and renovations. In 1965, Capital City Savings and Loan restored the structure and built a new wing addition. This reconstruction became known as the keystone example for rehabilitation in keeping with the Historic District. Visit Annapolis and Anne Arundel County (VAAAC) remodeled the landmark building in 1994 as the Visitors Center with offices and meeting rooms.

The Graduate Hotel & Power House

126 West Street

The building known as the Powerhouse, located on the The Graduate Hotel property has quite an interesting history. The old Washington/Baltimore & Annapolis Railroad originally constructed the three-story building in 1910 as a substation, providing electricity for the railroad and the entire city of Annapolis. After losing an anti-trust suit, it was sold to the Annapolis Dairy Products Co. in 1929. Subsequently, that business operated on the site until 1951 when it became the location of the Annapolis Bus Company.

The Graduate Hotel has undergone many renovations since its days as the Powerhouse. Photo courtesy of the author.

Then, in 1986, The Annapolis Hotel opened but was later sold to Loews Annapolis Hotel. In 1991, the Powerhouse became part of the existing hotel, providing 4500 square feet of additional space to be used for meetings, banquets and conferences. Renovation to the familiar landmark preserved the building’s original exterior design.

In 1991, the Powerhouse became part of the existing hotel Th new space provides 4500 square feet of meeting and conference space. Photo courtesy of the author.
Lois Villemaire

Lois Villemaire is retired from a career in local government and is now exploring her interest in creative writing, sometimes combined with researching family history. The latter has provided her with colorful and unique material. Lois enjoys walking around downtown and practicing yoga. She volunteers at The Wellness House of Annapolis, a strength and support resource for cancer patients, survivors, and their families. She lives in Annapolis with her husband and they love reading, restaurants, music, and spending time with their children and grandchildren.