Historical Architecture Tour with DC Design Tours

Tour Overview

Venture east of the Anacostia River into a neighborhood shaped by transformation and adaptation. Once home to the indigenous Nacotchtank and later developed as the Whites-only suburb of Uniontown, by the 1970s, Anacostia had grown into a center of Black culture, activism, and civic life.

Abolitionist Frederick Douglass spent his last 17 years at his Anacostia estate, known as Cedar Hill. Those same hills witnessed pivotal episodes in American history—from the burning of Washington in 1814 to John Wilkes Booth’s dramatic escape, to the 1932 Bonus Army protests. Today, historic rowhouses, ambitious preservation projects, a lively arts scene (including a brand-new museum), and ongoing development make Anacostia one of DC’s most dynamic and fast-changing neighborhoods to explore.

What We'll See

We start outside the Anacostia Arts Center, a 1937 Woolworth’s Department Store reborn as a cultural hub and small-business incubator. From there, we stroll beneath the glow of an iconic neon sign to the brand-new Go-Go Museum, celebrating DC’s homegrown Funk music style. Heading off the main drag and into residential streets lined with rowhouses—some lovingly restored, others still in flux—we’ll uncover surprising architectural details along Rose's Row and find traces of Anacostia’s rural roots. Along the way, we’ll pause at a pocket park with a story to tell and admire three churches, each with a distinctive style and unique history.

Next up is the neighborhood’s quirkiest landmark: the 19-foot-tall “Big Chair,” a 1959 publicity stunt that turned into a local icon, where a 21-year-old aspiring model, known as “Alice in the Looking Glass House,” lived uninterrupted for 42 days. We’ll also stop outside the former 11th Precinct police station, once a marker of Anacostia’s racial dividing line, heroically and colorfully repurposed in 1993 as a health center serving people with HIV.

Our final climb brings us to the foot of Cedar Hill, the home of Frederick Douglass, the “Sage of Anacostia.” Here, you’ll learn the inspiring story of Douglass and his second wife, Helen Pitts, whose dedication preserved this historic estate for generations.

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

Where to Meet

Our walking tour begins in front of the Anacostia Arts Center at 1235 Marion Barry Ave SE (formerly Good Hope Rd), and concludes in two hours near the Frederick Douglass House at the intersection of 14th St and W St SE.