On Cleveland Park's Connecticut Avenue, the Big Rooms Hold and the Small Storefronts Turn Over

In December 2021, the owners of Captain Cookie signed a ten-year lease for 3411 Connecticut Avenue NW. They had run their DC cookie and ice cream business for nine years by then, and they chose Cleveland Park because so many of their customers lived in upper Northwest. Getting the shop open took until the fall of 2023. By April 2026 the storefront was dark, with most of that lease still left to run.

That storefront sits in the middle of a short stretch that has had a busy year. A new tavern with a rooftop opened at 3421. Three smaller spaces nearby are empty or waiting on tenants. The businesses that have lasted longest on this part of Connecticut Avenue are large rooms that serve people across a whole day and evening. The small storefronts are where the costs of opening and operating on this block have weighed most heavily, and they are the spaces that keep changing hands.

What the owners of 3411 described

Captain Cookie's owners explained the closure in their own words in a note they gave to PoPville in July. They described a build-out that should have been "relatively simple and rapid." Instead it ran for years, slowed by DC permitting, "the historic nature and condition of our parcel," street construction that hit at the wrong moment, and supply chain delays. Once the shop opened, sales could not keep up with costs:

"In spite of a strong reputation and diehard neighborhood fans, we simply could not bring in enough revenue to support the astronomical and rapidly rising costs of labor, utilities, insurance and supplies."

The lease was signed in late 2021, and the doors opened nearly two years later, after delays the owners attributed to permitting, the historic parcel, and street work. The costs they listed are the same ones every business on the street pays. Their note ended by wishing luck to "the next business owner brave enough to try" in the space.

A few doors away, 3417 has been empty since Sakusaku Flakerie closed in December 2025, according to PoPville's reporting.

The opening that stuck: Highlands Tavern

Highlands Tavern took the old Cleveland Park Bar & Grill space at 3421 Connecticut Avenue, and Eater DC reports that it opened over Labor Day weekend. It is a much larger operation, with more floors, more seating, and more hours of the day to fill.

A PoPville announcement described it as a "family-friendly, multi-level neighborhood restaurant and bar" with a scratch kitchen overseen by George Grau, a DC native and Culinary Institute of America graduate. Co-owner Ki Yoon also co-owns Magruders, and Jeffrey Diaz runs daily operations and the beverage program. According to Eater, the owners also run Knowles Wine Station in Kensington.

The menu and setup are built for a long evening. Eater lists brick-oven pizzas, fish tacos, and Basque cheesecake. There are two levels of bars with house-made cocktail syrups and 12 taps, plus 14 TVs that lean toward Notre Dame and Washington Commanders football. A mural of the nearby Metro stop and the stone lions leads up to the rooftop patio. PoPville's announcement adds a kids' menu, burgers and handhelds, and a separate non-alcoholic list.

The practical details:

• Hours: Monday through Thursday 11 a.m. to 10 p.m., Friday and Saturday 11 a.m. to 11 p.m., Sunday 11 a.m. to 9 p.m., per the tavern's own site
• Weekday happy hour: $6 drafts, $7 margaritas or Old Fashioneds, $8 wines, as of Eater's September 22, 2026 update
• Rooftop: promoted on the tavern's site as a main draw

A family can come for lunch, a group can watch a full football game, and couples can stay on the rooftop after dinner, all in the same room. That spreads the same labor, utility, and insurance bills across many more hours and many more kinds of customers.

The rooms that have outlasted everyone

Highlands Tavern joins long-running businesses that work the same way. Atomic Billiards at 3427 Connecticut has called itself a neighborhood bar since 1993 and still runs happy-hour specials. Nanny O'Brien's at 3319 Connecticut runs a daily happy hour and a regular schedule of weekly events. Across the avenue, Byblos Deli at 3414 keeps regular service hours and posts a weekly special.

Pool tables, a weekly events calendar, and a weekly special each give people a reason to come back on a regular schedule. A bar that has lasted since 1993 has made it through every one of the cost pressures Captain Cookie's owners named.

The block, address by address

Here is the status of each storefront as reported through mid-October 2026.

On September 25, PoPville reported tips that Over Doughs Bagels would take 3411 and Handcraft Donuts would take 3417, and said it would post updates as it learned more. Handcraft already runs a handmade brioche doughnut shop at Union Market, 1309 5th Street NE, according to its own FAQ page. That page does not mention Cleveland Park. On October 13, PoPville passed along another tip that a Buffalo Wild Wings GO is coming to the former Tigi Salon at 3505. The item said the space would need a major buildout and that confirmation was still pending.

All three remain reported tips. If they pan out, the small spaces at 3411 and 3417 would go to bagel and doughnut shops, and the newcomers would face the same build-out conditions and operating costs Captain Cookie's owners described. Handcraft would open with an established shop already running across town.

The theater in the middle

The Uptown Theatre at 3426 Connecticut sits in the middle of the block, and it is still the biggest open question there. PoPville reported in March 2025 that a liquor-license notice proposed a multipurpose cultural-art venue there for immersive art, performance, and theater, with 25 seats and a total occupancy of 350. The most recent public update came in PoPville's December 30, 2025 report. It said the theater space was not for lease, "nothing has changed," and only two Connecticut Avenue storefronts in the building, 816 and 836 square feet, were still available. No newer status has been made public since then.

The plan described in that liquor-license notice, a large venue for performances and events, would fit the pattern of the rooms that have lasted here. The two small storefronts in the theater building are closer in size to the spaces that have changed hands.

The fourth Thursday without a market

This Thursday, October 22, is the fourth Thursday of the month. From April through September, fourth Thursdays brought the Cleveland Park Night Market to the 3400 block from 5 to 9 p.m. The 2026 season ran through September, with an August 27 date among those listed, so the block goes back to its regular storefront hours for the rest of fall. The removal of the old service lane, which PoPville credits with letting the "Cleveland Park Promenade" grow, gave these events the sidewalk room they need.

The next organized evening is on Friday, October 30. Cleveland Park Main Street's Halloween Bar Crawl runs from 7 to 10 p.m. with three stops:

1. Atomic Billiards, 3427 Connecticut Ave NW
2. Taco Cantina, 3321 Connecticut Ave NW
3. Nanny O'Brien's, 3319 Connecticut Ave NW

Two of the stops sit side by side at the southern end of the strip, and the third is a few doors up from Highlands Tavern's new rooftop.

At the Hagen Bergstrom Team, we keep a running record of Cleveland Park's storefronts and buildings, address by address. If you'd like to talk through what the changes on Connecticut Avenue mean for a home nearby, we would be glad to sit down with you. Book an Appointment whenever it suits you.