Pennsylvania Avenue: Murder Bay to Main Street

Tour Overview

Pennsylvania Avenue is more than a street—it’s America’s national stage. From presidential inaugurations and protest marches to funeral processions and parades, this broad boulevard has witnessed the nation’s triumphs and tragedies. But behind the pageantry lies a story of conflict and reinvention.

First envisioned by city planner Pierre L’Enfant as Washington’s “grand avenue,” Pennsylvania Avenue became notorious in the 19th century as the boundary of “Murder Bay,” a district of gambling dens, brothels, and saloons. By the 1940s, massive government-led redevelopment replaced the neighborhood with Federal Triangle; an imposing complex of Neoclassical office buildings that still dominate the landscape today.

On this two-hour walking tour, we’ll explore the White House neighborhood and trace the dramatic evolution of Pennsylvania Avenue itself, uncovering how design, politics, and power transformed Murder Bay into America’s Main Street.

What We’ll See

We begin in Lafayette Square, the symbolic front yard of the White House. Here, we’ll trace the evolution of 1600 Pennsylvania Avenue—from fires, floods, and near-collapse to the sweeping renovations that shaped today’s executive mansion. Nearby, the President’s Guest House, created from three historic homes, has hosted world leaders for decades. The colossal Eisenhower Executive Office Building, once the headquarters of the military and a 19th-century showcase of French Second Empire design, looms large across the street.

From there, we follow Penn Ave’s transformation from vice-ridden district to ceremonial boulevard. At the Willard Hotel, we’ll uncover tales of presidents, diplomats, and the origin of the word “lobbyist.” We’ll pause at the sobering National WWI Memorial (completed in 2024) and stroll through Freedom Plaza, a controversial 1980s addition to the avenue. We’ll walk thorough Federal Triangle, a massive Neoclassical complex of office buildings built to displace Murder Bay and discuss the seemingly out of place Old Post Office Tower, once nicknamed “Washington’s old tooth.” Passing the fortress-like brutalist FBI Headquarters and the contrastingly classical National Archives, we’ll see how architecture reflects changing ideas of government power.

Our walk concludes at the Temperance Fountain, one of Washington’s quirkiest landmarks. Easy to miss but rich with symbolism, it shows how even the smallest monuments tell national stories along America’s Main Street.

Tour Highlights

• The White House
• Eisenhower Executive Office Building
• Blair House (President’s Guest House)
• The Willard Hotel
• Old Post Office Tower
• J. Edgar Hoover FBI Building
• U.S. Navy Memorial
• National Archives
• Apex Building
• Temperance Fountain

Private & Group Tours

Experience this tour exclusively on your schedule! Available any day, any time, for groups of all sizes, from solo travelers and families to a full busload. Reserve your private walking tour for up to twelve guests via our online calendar or get in touch to arrange custom times, larger groups, driving tours, or personalized itineraries.

Where to Meet

Meet your guide in the center of Lafayette Square at the equestrian statue of Andrew Jackson.
GPS Address: 701 Jackson Pl NW Washington, DC 20005
Your tour ends near the Archives-Navy Memorial Metro Station.