The Cleveland Park Shuffle: What's New, What's Gone, and What's Still Dark on Connecticut Avenue

If you searched to see whether Captain Cookie was still open in Cleveland Park sometime this spring, you were not alone. Neighbors noticed the lights off during posted hours, the signage stripped from inside the window, and no answer at the old phone number. That confusion turned out to be the first sign of something bigger. Over the past twelve months, the short stretch of Connecticut Avenue between Newark and Macomb Streets has turned over more storefronts than any comparable block in the neighborhood has in years, and the pace has only picked up since June.

None of this is really about real estate. It is about knowing what's actually open before you walk over there expecting it, and about understanding why a strip that felt settled for a decade suddenly does not.

The Block, Before and After

Here is what has changed on the 3400 and 3500 blocks of Connecticut Avenue NW since last year, address by address.

Five storefronts, five different outcomes, all within about a block and a half. That density of change is the story. A single closing or opening is routine. Five in a year, on the same stretch, in the same twelve-month window, is not something this part of Connecticut Avenue has seen since before the pandemic.

Why the Cookie Shop Couldn't Make the Lease Work

The Captain Cookie closure is worth understanding because it explains something about the block that a simple "closed" sign does not. The owners signed a ten-year lease on the 3411 Connecticut Avenue space back in December 2021, after nine years running their cookies-and-ice-cream business elsewhere in the District and getting it through the worst of the pandemic. The buildout that followed took far longer than expected, slowed by the District's permitting process and by construction complications tied to the age and condition of the building. By the time the doors opened in September 2023, the ten-year clock was already well underway.

When the owners announced the closure this July, they pointed to the ordinary math of running a small food business in this corridor right now: rising labor costs, insurance, utilities, and supplies outpacing what a shop of that size could bring in. It is a specific, unglamorous explanation, and it is a useful one. It tells you the empty storefront at 3411 is not a sign the block is struggling. It is a sign that small independent operators are absorbing costs that larger, better-capitalized concepts down the street are built to withstand.

The New Anchor at 3421

That contrast shows up directly next door. Highlands Tavern is set to open before the end of August in the space that housed Cleveland Park Bar & Grill for years, a build-out its owners describe as a full reimagining of a historic multi-level room. The concept comes from George Grau, a D.C. native and Culinary Institute of America graduate who runs the scratch kitchen, and Ki Yoon, who also co-owns Magruders. Day-to-day operations and the beverage program fall to Jeffrey Diaz, an industry veteran, with Chicago-born chef Mathew Douglas leading the kitchen.

The menu leans toward wood-fired pizza, burgers, and handhelds, with a kids' menu, a twelve-tap draft list, and a dedicated non-alcoholic selection. The rooftop is the headline feature, and Highlands Tavern has already positioned itself as the official watch-party spot for Notre Dame football this fall, with sound and seating spread across the rooftop and the tavern's multiple levels. If your Saturday afternoons in the fall used to mean driving somewhere else for a game, that is no longer necessary.

Wine, Kebab, and a Mailroom

Two doors down, the retail turnover has been just as active, if less dramatic. Cork Market opened at 3504 Connecticut Avenue on January 8, combining a wine bar, a retail wine and specialty food shop, catering, and private event hosting in one space that sat vacant for a stretch beforehand. It is the kind of stop that changes a weeknight errand into an actual reason to walk down the block.

At 3417, in the space Al Volo used to occupy, Moga Doner House put up signage on May 7 and followed with a liquor license placard within days of Highlands Tavern posting its own. That is not a coincidence worth ignoring. Two liquor license applications going up on the same short stretch within a week of each other is a fair signal that this particular block is where new operators want to be right now, not somewhere else in the neighborhood. Moga's filing lists a modest indoor footprint with room for 26 seated and 10 standing, plus a summer garden built to hold 75.

A few doors up, inside the historic Sam's Park & Shop building, a UPS Store opened this spring after construction was spotted in March. It is not a restaurant and it will not show up on anyone's list of neighborhood dining news, but for residents who ship packages or need a mailbox, it is the kind of practical addition that matters more day to day than another cocktail menu.

The Marquee That Still Won't Light

Set against all that motion, one storefront on this same stretch has not moved at all in six years, and it happens to be the neighborhood's most visible.

The Uptown Theater closed in March 2020 when AMC's lease expired, ending an 84-year run that included the world premiere of 2001: A Space Odyssey in 1968 and Jurassic Park in 1993. The building earned a spot on the National Register of Historic Places in December 2022, which protects its Art Deco facade but does nothing to determine what happens inside it. A group of neighbors and hospitality veterans tried to raise money for a community-run nonprofit version of the theater in 2023, pulling in half a million dollars in commitments within three days, but the proposal was not accepted by the Pedas family, which still owns the underlying building.

In October 2024, Sandro Kereselidze and Tatiana Pastukhova, the husband-and-wife team behind the experimental art space Artechouse, signed a twenty-year lease on the Uptown and described plans for some kind of cultural arts venue blending old-school Hollywood with new technology. A liquor license application surfaced in March 2025 describing a multipurpose space with a modest seating capacity of 25 but a total occupancy load of 350, suggesting something closer to a performance and event venue than a traditional cinema. There has been no real update since that filing. A local news blog checked in on the project again this July and found nothing new to report.

So the block keeps turning over everywhere except its most prominent address. That is not a contradiction. A single-screen movie palace with a twenty-year lease and an ownership group that also has to finish renovating its own flagship art space downtown is playing a much longer game than a wine bar or a doner shop. Worth watching, not worth waiting on.

What Doesn't Turn Over

If Connecticut Avenue is the part of the neighborhood in flux, Rock Creek Park is the part that has stayed exactly the same, which is its whole appeal. A few options worth knowing, whether you are filling a Saturday morning or just need to get out of the house after a long week:

• The Klingle Valley Trail is a 0.7-mile paved path that opened in 2017 on the former roadbed of Klingle Road, connecting Cleveland Park to Woodley Park and Mount Pleasant. It passes under Connecticut Avenue through a large arched bridge and links directly to the Tregaron Conservancy, a 13-acre former estate with meadows, streams, and a lily pond.
• The Melvin C. Hazen Trail, sometimes listed as Reservation 630, is a roughly two-mile out-and-back path starting near Reno Road and Tilden Road. It follows a stream tributary down to Rock Creek and involves a few stream crossings, so wear shoes you don't mind getting wet.
• Both trails feed into the larger Rock Creek Park network, giving you a car-free route toward the National Zoo or south toward Georgetown if you want to turn a short walk into a longer one.

None of that has changed in years, and none of it is likely to. That contrast, a commercial strip reshuffling five storefronts in a single year against a trail network that has looked the same since 2017, is the actual shape of life in Cleveland Park right now. The wooded half of the neighborhood is the constant. The retail half is where you need to keep checking.

If you're weighing what any of this means for your own property here, whether it's timing a sale around the neighborhood's current momentum or simply understanding how these changes affect what buyers notice on a walk down Connecticut Avenue, Advisory Partners can talk through it with you directly. Request a private consultation whenever the conversation is useful, not before.