Our Story

A CLEVELAND PARK ORIGINAL

Rooted in History. Raised on the Rooftop.

Aerial view, southeast along Connecticut Avenue corridor form north of the historic boundary at Woodley Park. – Connecticut Avenue, Washington, District of Columbia, DC

Before It Was Cleveland Park

Long before this stretch of Connecticut Avenue was known as Cleveland Park, the locals simply called it “the Highlands”—a name we’ve borrowed with pride. It was an elevated escape from the humidity of downtown D.C., where summer breezes met shaded porches. When you step through our doors today, you’re stepping into that exact same tradition: a place to retreat, unwind, and watch the neighborhood move below.

Oak View (also known as Red Top), the residence of President Grover Cleveland at 3542 Newark St., NW, Washington, D.C.

The Summer White House on the Ridge

The neighborhood’s enduring name traces back to President Grover Cleveland, who escaped the dense heat of downtown D.C. by establishing his country retreat, Oak View. Locals took to calling the house “Red Top” for its red-shingled roof, and soon the entire hillside took on his name. That same desire for open skies and cool evening breezes is what shaped our rooftop. Consider Highlands Tavern our modern take on the tradition: high above the city, cold drink in hand, taking in the neighborhood below.

Aerial view, southeast along Connecticut Avenue corridor form north of the historic boundary at Woodley Park. – Connecticut Avenue, Washington, District of Columbia, DC

Before It Was Cleveland Park

Long before this stretch of Connecticut Avenue was known as Cleveland Park, the locals simply called it “the Highlands”—a name we’ve borrowed with pride. It was an elevated escape from the humidity of downtown D.C., where summer breezes met shaded porches. When you step through our doors today, you’re stepping into that exact same tradition: a place to retreat, unwind, and watch the neighborhood move below.

Oak View (also known as Red Top), the residence of President Grover Cleveland at 3542 Newark St., NW, Washington, D.C.

The Summer White House on the Ridge

The neighborhood’s enduring name traces back to President Grover Cleveland, who escaped the dense heat of downtown D.C. by establishing his country retreat, Oak View. Locals took to calling the house “Red Top” for its red-shingled roof, and soon the entire hillside took on his name. That same desire for open skies and cool evening breezes is what shaped our rooftop. Consider Highlands Tavern our modern take on the tradition: high above the city, cold drink in hand, taking in the neighborhood below.