D.C. Neighborhood Spotlight: Cleveland Park

You don’t have to look too far in D.C. to discover interesting history. Cleveland Park is chock-full of it.

Nestled between Rock Creek Park, the Smithsonian National Zoo, and the National Cathedral, Cleveland Park has a desirable location just far enough from the main business districts to feel residential, and close enough to be convenient. It is served by Metro’s red line (Cleveland Park stop), as well as a number of bus lines that run up Connecticut Avenue.

It became desirable back in the 1700s because it was up on a hill, offering unobstructed views of Washington and the surrounding countryside. Most importantly, the breeze on the hill provided relief from the hot, swampy atmosphere closer to the Capitol.

A Quick Rundown of Highlights from Cleveland Park’s History

  • The oldest house in the District is in this neighborhood – a section of a farmhouse that was built in the 1730s.
  • President Grover Cleveland once had a summer home, “Oak View,” in the area. The neighborhood later became known as Cleveland Park after its famous resident. (The home was demolished in 1927.)
  • Cleveland Park was one of the District’s first “streetcar suburbs” after electric streetcars were installed on Wisconsin Avenue and Connecticut Avenue in the 1890s.
  • Keeping with the transportation theme, one of the first strip malls in the country was built on Connecticut Avenue. The “Park and Shop” offered free off-street parking to customers, a new and very desirable concept as parking was a huge problem then as it is now.
  • The Uptown Theater, which dates back to 1939,  is a fantastic example of art deco architecture and is one of the last remaining period theaters in Washington.

What to Do in Cleveland Park

Though the area is mostly residential, there are some cool things to do in Cleveland Park. The neighborhood receives far fewer tourists than the National Mall and museums, so you can get a true taste of how the (affluent) locals live by spending an afternoon here.

  • Dining: There are a number of good bars and restaurants along the main strip on Connecticut Avenue. Indique and Ardeo offer great brunches. You can get your steak fix at Medium Rare. Ripple was named one of D.C.’s top 100 restaurants by Washingtonian Magazine in 2016.
  • Hiking: Rock Creek Park bounds Cleveland Park to the east. It’s easy to connect up with the Western Ridge Trail to immerse yourself in nature and enjoy the lovely scenery that the park offers. Read more about hiking Rock Creek Park here.
  • Sightseeing: The Uptown Theatre, fire station, and old Walgreens are architectural gems. If you meander down any of the side roads into the neighborhoods (Macomb and Newark Streets being particularly good), you’ll see some lovely, historic single-family homes housing the city’s more affluent population. Be on the lookout for old fire and police call boxes that feature original artwork and historical vignettes about the area.

    D.C. Neighborhood Spotlight: Cleveland Park

    Hanging out by the traditional red doors at the fire station.

  • Movie-Going: A visit to the Uptown Theater is a must. The theater is old, unassuming on the inside, and incredibly charming. It reminds me of what it used to be like to go to the movies as a kid.
  • Strip Mall Shopping: We may be used to strip malls these days in the U.S., but they were once an innovation! It’s worth it to grab a fro-yo or a bottle of wine from Weygandt Wines (a highly regarded wine shop in its own right, noted for its French wine selection) just to say you stopped into one of the first strip malls in the country.
Weygandt Wines Cleveland Park
Turtleneck: Banana Republic (similar)

Vest: Banana Republic (similar)
Leggings: Ann Taylor
Boots: Khombu (similar)
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Where to Stay

You’re not going to find much in the way of hotels in Cleveland Park. It’s much more of a residential area. However, nearby Woodley Park has a number of hotels to choose from (though they’re on the pricier end). If you want to stay nearby and are on a budget, try Airbnb or head up to Van Ness, one metro stop away, for some more affordable options.

When to Go

Spring and fall are great times to visit Washington. Unless you plan to hike in Rock Creek Park, you shouldn’t need more than an afternoon to visit Cleveland Park. It’s a great area to grab brunch – a Washington tradition – and take a walk afterwards while you digest. The National Zoo is a short walk down Connecticut Avenue, so you can easily pop up to Cleveland Park before or after a zoo visit.

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D.C. Neighborhood Spotlight: Cleveland Park