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By Christine Fillat


Above image photography by Geoffrey Hodgdon


On a 347-acre landmass overlooking the Chesapeake Bay, just south of the city of Annapolis, the sea air is as much a part of life in Bay Ridge as the trees and grass. The area is entirely residential; Farragut Road leads into and out of the neighborhood of 460 homes. There is no vernacular to the residences; winterized ’20s summer cottages share space with more modern homes and the occasional mini-mansion.

With the Severn River, Lake Ogleton, and the Chesapeake Bay surrounding the community, water is a formidable presence in daily life. It’s that proximity to the water that sets the tone for the whole community. “It doesn’t matter if it’s the middle of the summer or January: there are always people out riding bikes, running, walking, doing outdoor activities and taking in the views,” states Gretchen Littlefield, Bay Ridge resident.

Bay Ridge is uniquely suited for families. Littlefield lives here because this is a community where her daughter can run and play and ride her bike unsupervised. “People’s children grow up together,” she says. “It’s like something out of the 1950s.”

What contributes to this air of nostalgia? Bay Ridge was first farmed in the 17th century. In the late 19th century, a grand Victorian resort was developed here. Folks arrived by steamship and railroad from Baltimore and points beyond. Thousands of post-Civil War folks visited what was then known as the “Queen Resort of the Chesapeake.” After the resort went belly-up in the early 1900s, developers began to subdivide the area for summer cottages. In the ’20s, modest summer cottages gave way to year-round homes. Presently, it’s not uncommon for several generations of some families to live on the same block.

You get the feeling that the community is a well-oiled machine. There’s a pool, a yacht club, and lots of committees to join. Early on, a civic association was established to address issues that came with the waterfront location: erosion, safety, and general land maintenance. Bay Ridge has a tradition of community celebrations, as well: a beach party to mark the beginning of the summer season (with everyone wearing matching t-shirts), a Fourth of July parade, and an end-of-season fundraiser. These get-togethers help to galvanize the families and neighbors in Bay Ridge.

In March 2002, the Bay Ridge Trust purchased 110 acres of forested land slated for development. Now that the land is owned by the community, it is forever protected from any sort of development. They call this land The Big Woods, and the people of Bay Ridge are fully invested in taking care of the forest. Beyond preserving the unique wooded character of the area, The Big Woods is also environmentally valuable. Families adopt individual plots of the forest to keep it healthy and free from invasive species.

In 2022, Bay Ridge will celebrate the community’s centennial and the 20th anniversary of buying The Big Woods. And so it goes; life continues.



The evolution of Bay Ridge—from colonial farmland to grand Victorian resort to summer coterie to the present-day community—is lovingly documented in Jane Wilson McWilliams and Carol Cushard Patterson’s seminal book, Bay Ridge on the Chesapeake (Brighton Editions, 1986). Life in Bay Ridge throughout the ages comes alive through carefully curated historical documents and photographs. This delightful read is a virtual journey back in time. The authors are hoping to reissue the book in time for the Bay Ridge Centennial.

The historical photographs are courtesy of Jane Wilson McWilliams and Carol Cushard Patterson

Above left: The Bay Ridge Hotel c.1900 stood atop Tolly Point overlooking the Chesapeake Bay.

Above right: Upon Tolly Point Beach, with steamship pier in the background. 1887



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Annapolis Home Magazine
Vol. 11, No. 6 2020