In the 1890s, if you held one of Washington's finest addresses, there was a fashionable way to spend an evening: climb aboard a tally-ho coach at one of the grand downtown hotels, clatter across the brand-new Pennsylvania Avenue bridge, and ride up the heights east of the river to dinner. The destination was the Overlook Inn — a resort hotel on the plateau of what is now Hillcrest, and for a few glittering seasons, the sensation of the capital's social calendar.
The coaching-resort fashion of the day: tally-ho coaches arriving at a resort hotel in 1889 — photographed in the Adirondacks, but precisely the scene the Overlook Inn staged on Hillcrest's plateau. Library of Congress.
First, a Fort
The plateau had strategic value before it had social cachet. During the Civil War, the ring of earthwork forts defending Washington ran along these heights, and Fort Baker held this stretch — part of the chain guarding the Navy Yard and the eastern approaches to the capital. When the war ended, the guns left, but the earthworks stayed, and the high ground went back to being farmland with one exceptional feature: the finest views in the District, from the city's highest plateau.
The neighborhood's early promoters knew exactly what they had. Brochures of the era boasted that the heights offered particularly pure air and ran five to ten degrees cooler than the swampy city below — no small pitch in a Washington summer before air conditioning. The area's admirers reportedly included President Grover Cleveland, who is said to have tried to buy property on the heights — until the farmer, learning exactly who his buyer was, raised the price, and Washington narrowly missed having a second Cleveland Park.
The Inn on the Plateau
In 1894, a group of wealthy industrialists put a resort on that reputation. They hired Appleton P. Clark, Jr. — one of the most prolific architects Washington ever produced — and built the Overlook Inn on the W Street plateau, right beside the remains of Fort Baker, with Fort Baker Drive laid out as its grand front approach.
The business model was pure 1890s theater. The Inn hired teams of horse-drawn coaches to collect Washington's high society from the fancy hotels downtown and parade them across town, over the four-year-old iron bridge at Pennsylvania Avenue, and up the hill — where fine cuisine and sweeping city views waited at the top. For several years it was, by contemporary account, the sensation of Washington's power elite.
Six Seasons, Then Silence
The Overlook Inn's run was brilliant and brief: 1894 to 1900. The coaching-party fashion faded as quickly as it had arrived, and the resort era on the plateau closed with the century.
But the Inn had done something durable: it taught fashionable Washington that the heights east of the river were somewhere worth going. Within a few years, developer Arthur Randle — whose streetcar suburbs were already climbing the hills nearby — was platting Hillcrest itself, and the plateau the coaches once climbed filled in with the brick colonials, Tudors, and generous lawns that define the neighborhood today.
What the Street Grid Remembers
The Inn is long gone, but its geography survives in plain sight. Fort Baker Drive still traces the old front approach. And on the Inn's former site at 2911 W Street SE stands a remarkable successor: a 1935 Art Deco house by John Joseph Earley, the pioneer of exposed-aggregate concrete whose other credits include Meridian Hill Park and the original National Airport terminal. Historian James M. Goode named it among DC's 100 most architecturally significant residences — which means the plateau has now hosted landmarks in three different centuries.
Hillcrest itself remains what the Inn's promoters promised: high ground, big trees, and some of the best-kept lawns in the city — a neighborhood of detached brick colonials and Tudors that hosts annual garden tours, with the rebuilt Skyland Town Center as its revitalized retail core and new townhouses rising there with straight-shot views of the Mall.
Buying on the Plateau Today
Hillcrest's housing stock is the kind lenders like: detached houses on real lots — no condo project review, no association dues in your ratios — with midcentury and prewar construction that occasionally rewards a renovation loan, and decades of quiet appreciation behind it for longtime owners weighing a cash-out refinance or home equity loan. Our neighborhood guides cover the surrounding east-of-the-river markets, with Randle Highlands just down the avenue.
Thinking about a house on the heights the coaches once climbed? Get pre-qualified or talk to us first — we'll bring the numbers, you bring the view.
