Historic Walking Tour of Dupont Circle in Washington DC

Tour Overview

Gilded Age mansions, high-stakes diplomacy, and sordid scandals converge in Dupont Circle, once on the rural edge of the capital and later a playground for Washington’s wealthy. Today, its tree-lined streets showcase some of the city’s most striking architecture, from stately Neoclassical residences to eclectic Arts & Crafts homes.

On this two-hour walking tour, we’ll trace the evolution of Embassy Row and the surrounding Dupont neighborhood, uncovering the stories behind the grand façades. Meet the city’s social climbers, power brokers, and eccentric residents—from influential socialite Alice Roosevelt Longworth to Evalyn Walsh McLean and her infamous Hope Diamond. Here, architecture and ambition intertwine with the story of Washington’s dramatic turn-of-the-century transformation.

What We'll See

We begin at Dupont Circle’s eponymous fountain, a Beaux-Arts centerpiece by the designers of the Lincoln Memorial. We’ll discuss how this once-rural outpost evolved into a showcase of Gilded Age ambition, where wealth and social status were expressed through architectural splendor.

Strolling down Massachusetts Avenue, now known as Embassy Row, we’ll take in a parade of Queen Anne, Neoclassical, Baroque, and Beaux-Arts mansions, many now serving as embassies. Highlights include the opulent Indonesian Embassy, once home to the Hope Diamond; the imposing Anderson Mansion, headquarters of the Society of the Cincinnati; and stories of residents such as inventor George Westinghouse, artist Alice Pike Barney, music legend Ahmet Ertegun, and notorious governor Alexander “Boss” Shepherd.

Turning into the quiet streets of Kalorama (“beautiful view” in Greek) we’ll stop at the Woodrow Wilson House before descending the Roman-inspired Spanish Steps and passing the whimsical Hobbit House. Our walk concludes at the Phillips Collection, America’s first modern art museum, set within an elegant Italianate mansion.

From extravagant façades to tucked-away architectural gems, this tour reveals how design helped shape and flaunt power in one of DC’s most refined neighborhoods.

Private & Group Tours

Private tours are available any day and time, for groups of all sizes! Check our private bookings calendar to reserve a walking tour for groups of up to twelve people. For times not listed online, groups larger than twelve, driving tours, or custom itineraries, please get in touch.

Tour Details

2 hours 1.5 miles Children under 5 years old are welcome to join for free. Sturdy walking shoes, bottled water, and comfortable clothes are recommended!

Where to Meet

Meet your guide in the center of Dupont Circle at the base of the fountain. GPS Address: 1 Dupont Cir NW, Washington, DC 20036 The tour ends in front of the Phillips Collection at 1600 21st Street NW.