The Rooftop Opened. The Marquee Still Hasn't. What That Says About Cleveland Park Right Now

"My goal is to reinvent the venue with the latest technology to stay relevant for the next hundred years," Sandro Kereselidze told a reporter in October 2024, describing his plans for the Uptown Theater. Two years later, the marquee at 3426 Connecticut Avenue is still dark. Two doors down, a rooftop bar with no such ambition opened in August, filled up on a Saturday, and started booking Notre Dame football watch parties.

That gap is the actual story of Cleveland Park's commercial strip this fall. Not a comeback, not a slump, but two different clocks running on the same block, and knowing which one you're standing under tells you more about the neighborhood than any single headline could.

The Building Everyone's Waiting On

The Uptown has been closed since March 2020, when AMC let its lease expire and pulled the projector out for good. That's six and a half years dark for a single-screen movie palace that once hosted the world premiere of "2001: A Space Odyssey" and was one of only 32 theaters nationwide chosen to screen the original Star Wars on its opening day in 1977. The building earned a spot on the National Register of Historic Places in December 2022, which protects its yellow-brick, limestone-fluted Art Deco facade but does nothing to speed up what happens inside it.

In October 2024, Kereselidze and his wife Tatiana Pastukhova, the couple behind the experiential art space Artechouse, signed a 20-year lease and announced a project called UPTOWN Experiences. Neither has offered a firm timeline. The only concrete update since came in March 2025, when a liquor license placard appeared in the window describing a "multipurpose establishment" for immersive art, performance, and theatrical experiences, with a modest 25-seat capacity and a 350-person occupancy load. That's a fraction of the roughly 850 seats the Uptown held after its last major renovation in 1996.

None of that is a criticism of the new owners. A 90-year-old single-screen theater with one enormous curved auditorium doesn't reopen the way a restaurant does. Every system inside a building built for one purpose in 1936 has to be reconceived for a different one, and that kind of renovation runs on a timeline measured in years, not seasons. The Washington Post's 2024 coverage noted the lease itself, at 20 years, is a bet on a very long horizon. Six and a half years of vacancy so far is consistent with a project that size, even if it doesn't feel that way to anyone who walks past the boarded windows on their way to the Metro.

Two Doors Down, a Faster Bet

Highlands Tavern didn't need a landmark designation, a liquor license placard, or a two-year lease negotiation to open its doors. It moved into the old Cleveland Park Bar & Grill space at 3421 Connecticut Avenue, kept the multi-level bones of the building, and had its official opening announced in mid-August 2026, before the month was out.

The people behind it aren't strangers to the neighborhood's food scene. George Grau, a D.C. native and Culinary Institute of America graduate, runs the scratch kitchen. Ki Yoon, who co-owns Magruders, is a co-owner here too. Jeffrey Diaz, an industry veteran, handles daily operations and the beverage program. What they built is deliberately flexible: wood-fired pizzas and handhelds for a weeknight crowd, a kids' menu for families walking over from the library, a 12-tap draft list and a non-alcoholic selection for whoever's driving, and a rooftop that can pivot from a quiet Tuesday to a full house on a Saturday when Notre Dame is playing.

That's the difference. Highlands Tavern didn't have to solve one enormous architectural problem before it could open. It inherited a building that already worked as a restaurant, made cosmetic changes, and started serving people. The Uptown has to solve its enormous architectural problem before it can do anything at all. Neither approach is wrong. But if you're trying to read whether Cleveland Park's commercial strip is moving fast or slow this year, the answer depends entirely on which kind of building you're asking about.

The Corner That Predates Both of Them

One block south, at Connecticut and Ordway, sits a third kind of building with the same underlying problem. Sam's Park and Shop was built in 1930, which makes it one of the earliest shopping centers in the country, not a later intrusion into an older streetcar-era block as it might appear. Its gables, dormers, and vaulted roofline earned it recognition as a contributing property in the Cleveland Park Historic District, which means an owner can't simply tear it down or radically reshape it, whatever the market wants.

That protection is now cutting the other way. A recent look at the property found its parking lot sitting roughly 90 percent empty most of the time, even though the building still holds a handful of smaller tenants and no longer counts a Target among them. The explanation isn't that shoppers have abandoned the corner. It's that Cleveland Park's on-street metered parking, at around $2.50 for the first hour, is cheap enough and close enough that most people never pull into the lot at all. A mostly empty parking lot in front of a mostly occupied building creates an optical problem the building didn't earn. It looks like a "dead mall" from the street even when it isn't one, which matters if you're the person deciding whether to lease the next vacant storefront there.

Like the Uptown, Park and Shop is stuck with a format from a different era of how people got around this corner. Unlike the Uptown, nobody has signed a 20-year lease to reinvent it. It just sits there, historically protected and functionally underused, waiting for someone to figure out what a 1930s auto-oriented format is supposed to do in a neighborhood built almost entirely around a streetcar stop.

What's Actually on the Calendar

None of this changes what there is to do here this month. Cleveland Park's Main Street organization, run through District Bridges, joins Van Ness and Tenleytown each fall for Art All Night, the kind of evening that turns storefronts and sidewalks into temporary gallery space regardless of what's happening with the Uptown's liquor license.

And the neighborhood's daily rhythms keep running on their own schedule. Ward 3, which covers Cleveland Park along with Woodley Park and Chevy Chase, has more dog parks than any other ward in the city at five, according to an Axios count from September 2026. That's one more than Ward 2, which covers Shaw, Logan Circle, and Georgetown combined. If your evening routine involves a leash and a familiar loop, that infrastructure isn't waiting on anyone's renovation timeline.

A few things worth knowing if you're planning your week around Connecticut Avenue right now:

• Highlands Tavern's rooftop is open nightly and is the designated watch-party spot for Notre Dame football this fall.
• The Uptown's windows are still papered over. There's no public opening date, so treat any social media chatter about a reopening as speculation until the owners confirm it themselves.
• Park and Shop's lot looks emptier than the building actually is. Its remaining tenants are still open for business even on the quietest afternoons.
• Art All Night returns this fall across Cleveland Park, Van Ness, and Tenleytown, coordinated by the three neighborhoods' Main Street groups.

The honest read on Cleveland Park this September isn't that the strip is thriving or stalling. It's that a hundred-year-old commercial corridor is made up of buildings with very different capacities for change, and this fall happens to be the moment when you can see all three speeds running side by side. A tavern that reopened in weeks. A theater still dark after six and a half years, two of them under new ownership with no announced reopening date. A 1930s strip mall protected from demolition but unable to solve a parking problem that's mostly a perception problem. Walk two blocks and you'll pass all three.

If you're the kind of resident who tracks this stuff block by block, you already know Cleveland Park doesn't move as one thing. It moves as however many things are happening on Connecticut Avenue at once, and this month there are at least three worth watching.

Curious how a stretch like this affects home values or what a listing near a corridor like this one might be worth to a buyer down the line, the team at Robert & Tyler has spent years tracking exactly these patterns across Cleveland Park and the rest of DC's close-in neighborhoods. Reach out any time you want a local read on what's actually happening on your block.