Well before chain eateries and shopping malls blanketed the Northern Virginia landscape, Herndon’s downtown area developed along one critical vein: the Washington & Old Dominion Railroad. The town began in 1858 when it was named after Commander William Lewis Herndon, a U.S. Navy explorer and naval hero. Subsequent to its namesake was a slow build-up of a compact, interrelated community where commerce, transportation, and taverns were the pillars of daily existence.
Among the buildings that have been a part of this town’s built landscape since the 19th century, one on the corner of Elden and Spring Streets is notable—not only for its longevity, but for all the lives it has had. The structure, now home to Jimmy’s Old Town Tavern, is estimated to have been built around 1897. That places its beginning only a few decades following Herndon’s incorporation in 1879, and at the peak of the railroad’s power over the area. Its original purpose was a dual-use tavern and general store, a function typical of small-town commercial centers of the late 1800s.
As Herndon transitioned from a country outpost to a more residential Washington, D.C. suburb, this building evolved with the times. Throughout the 20th century, it was home to a succession of businesses that both stayed in line with economic trends and the changing requirements of the community. During the early 1900s, the Wilkens and Brothers Bargain Store filled the space, selling general merchandise to a burgeoning population. Later, the building housed several different retailers, ranging from grocery stores to butcher shops and even a sporting goods store—each occupant adding still more history to the building’s physical form.
By the time the 1990s arrived, the town of Herndon had changed substantially. While the railroad was no longer the community’s lifeblood, remnants of that era lingered. Preservation of its core historic district became more intentional, with an effort to honor both the look and the spirit of the original buildings. It was during this period, in May 1997, that James Cirrito opened Jimmy’s Old Town Tavern in the long-standing structure. Cirrito, originally from Buffalo, New York, brought with him a new concept, but one that would coexist within the town’s historic framework.
What distinguishes the tavern today isn’t just its menu or community events—it’s the architectural preservation that subtly binds the past and present. Inside, oak finishes, antique brass fittings, and aged woodwork preserve the character of a much older establishment. Rather than gut the space for modernity, the tavern leans into its past. Many of the details have been restored or maintained to evoke the look and feel of its original construction at the turn of the century. That commitment to preservation is part of what makes the building more than just a business—it’s a kind of living document of Herndon’s transformation.
Cultural memory also plays a role in the building’s ongoing story. Local lore has it that the tavern is haunted by a ghost named Walter, a presence whose name has been passed down by employees and locals alike. Whether as storytelling or shared belief, these tales create another connection to the past. Reports have ranged from the playful to the unsettling. Staff members have claimed to see objects move or hear unexplained noises, especially in the adjacent prep house next door. One account describes a contractor’s power tool switching on unexpectedly while “Walter” was being discussed. Another describes trays mysteriously arranged in circles and doors opening on their own. These stories concerning Walter are more than twenty years old, and while unverifiable, they’ve become an informal oral history for the space.
These stories, while anecdotal, carry significance. They’re part of the folklore that shapes a place’s identity, not unlike the myths that form around old train depots or Civil War battlefields. Walter the Ghost has become one of those narratives that lends the building a certain personality, and locals, even skeptics, acknowledge its place in the tavern’s lore.
Throughout its years of operation under Cirrito, the tavern has remained at the crossroads of preservation and community participation. The structure’s original walls have hosted hundreds of fundraisers, concerts, and town celebrations. But even before Jimmy’s, the space functioned as a gathering spot in various forms—each iteration connecting generations of Herndon residents in a shared physical space. People from all walks of life—day laborers, federal employees, doctors, tradespeople, and tech professionals alike—gather under one roof. It’s a spot where “everyone is treated like a regular,” a guiding ethos that has helped the tavern become more than just a neighborhood restaurant; it’s become a local institution. That continuity, even through changing business names and ownerships, helps solidify the location as a landmark within the town.
Herndon itself, while relatively small in terms of population, hovering around 24,000 as of the 2020 census, has maintained a strong sense of identity in part due to structures like this one. Downtown development has largely respected the original layout of streets and buildings, and preservation initiatives have received both community and municipal support. Architectural surveys and local zoning efforts have helped safeguard older buildings from demolition or inappropriate redevelopment, particularly those located in or near Herndon’s officially recognized Historic District.
When considered alongside the larger timeline of Herndon’s evolution, the building that houses Jimmy’s Old Town Tavern stands as a reminder of the layers that define any town’s growth. Its survival is not merely coincidental but speaks to how local heritage is curated through intentional use and maintenance. While the tavern as a business is only one chapter, the structure’s history encompasses generations of commerce, social life, and architecture tied to Northern Virginia’s broader development.
In examining its role today, the building’s relevance lies less in novelty and more in what it represents. It serves as a physical anchor amid suburban change, its preserved features offering a tangible connection to a time when Herndon was a much smaller place, oriented around a train station and a handful of main streets. That bond is strengthened by the history shared within its walls—from “Walter the Ghost” to memories of previous shopkeepers, each contributing to its position in the town’s shared past.
As of 2025, the building still stands for its original function, albeit with some updates. Its oak features are still evident, its integrity maintained, and its presence in the community steadfast. Whatever brings them—be it the cuisine, the music, or the tales—they are entering more than a tavern; they are entering a place defined by over a hundred years of small-town fortitude, defined as much by yesterday as by the individuals who make it current today.
