In December 2021, the owners of Captain Cookie signed a 10-year lease at 3411 Connecticut Avenue NW. Opening took years. In a note to neighbors, the owner listed the delays: DC permitting, the historic condition of the parcel, supply chains, and "street-level construction that timed poorly with our own project." The ribbon cutting came in fall 2023. By July 2026 the shop had closed. The owner said revenue could not keep up with "the astronomical and rapidly rising costs of labor, utilities, insurance and supplies."

On September 25, PoPville reported a tip that Over Doughs Bagels will take the space. The post opened by crediting the removal of the old service lane, saying the Cleveland Park Promenade continues "to bloom" and calling the block a "pedestrian paradise." The street work that slowed one tenant down is now how the block's next tenants are being introduced. On the 3400 block, new operators are leasing the promenade as much as the storefronts, and their own filings show it.

The Seat Counts Point Outdoors

The former service lane by the Uptown is now a single-level pedestrian walkway that stays closed to cars. It was planned for restaurant patios, seating, landscaping, and room for markets and pop-ups. Liquor-license placards on the block show how operators plan to use it. A placard lists the seats a business intends to serve, and on this block the outdoor numbers carry the plan.

Moga Doner House stands out. It fills the former Al Volo space, put up signage on May 7, and posted a Class C restaurant placard that month. The placard plans for nearly three times as many seats outside as inside. Club Soda's February placard asked for a tavern license with 100 seats, a 72-seat sidewalk café, and entertainment endorsements. Neither business has publicly confirmed an opening as of late September. Moga's most recent update is the May placard, and Club Soda's is the February one. For now they are plans on file, not places to book dinner.

Highlands Tavern Is Open

Highlands Tavern announced its opening for Saturday, September 5, at 11 a.m. By late September its website showed a full menu, hours, and rooftop details. It is a multilevel, family-friendly restaurant and bar at 3421 Connecticut. George Grau, a D.C. native and CIA graduate, founded it and runs the scratch kitchen. His co-founder is Ki Yoon, co-owner of Magruders, and industry veteran Jeffrey Diaz runs daily operations and the beverage program. The menu covers wood-fired pizzas, burgers, handhelds, and a kids' menu. The bar has 12 draft taps and a dedicated non-alcoholic selection.

The rooftop is what sets it apart. It seats 60 in the open air, with full bar service and food from the wood-fired oven. Walk-ins are first come, first served. Reservations are available for parties of up to 15. Hours are 11 a.m. to 10 p.m. Monday through Thursday, 11 a.m. to 11 p.m. Friday and Saturday, and 11 a.m. to 9 p.m. Sunday. It is the first of this year's promenade-facing restaurants to open, which makes it the clearest test of whether the outdoor-seating plans hold up.

Turnover in Both Directions

The tenants leaving the block left at the same pace. Sakusaku Flakerie, at 3417 Connecticut, posted a closure notice in early December 2025. Fat Pete's Pizza & BBQ, at 3407 Connecticut, held its farewell weekend ending Saturday, August 29, 2026. Its notice gave no reason and said nothing about the space. Captain Cookie still bakes in the city at Western Market in Foggy Bottom, at the Tastemakers incubator kitchen in Brookland, and from its food trucks.

Two of those vacancies already have reported successors. The September 25 PoPville tip names Over Doughs Bagels for the former Captain Cookie space and Handcraft Donuts for the former Sakusaku space. Neither has an announced opening date. If both open, the block's morning trade turns over completely: a cookie shop and a pastry shop out, a bagel shop and a donut shop in.

The same street number appears more than once in these reports, so read them carefully. Moga Doner House and Sakusaku are both reported at 3417 Connecticut, and PoPville's December 2025 report on Sakusaku's closure described Moga as coming next door. Handcraft's exact unit will be clearer once signage goes up.

Across Connecticut, a Different Format

The 3500 block opposite the promenade has been running on a different model. Cork Wine Bar opened its Cleveland Park location at 3504 Connecticut Avenue on Thursday, January 8, 2026. Eater describes it as a 20-seat counter-service space. It combines a wine bar and market, with roughly 350 bottles and a small-plates menu. It is small, indoors, and partly retail, so it works the same in March as in June.

In the historic Sam's Park & Shop, Target at 3505 Connecticut was scheduled to close November 1, 2025, and the closure was attributed to "prolonged underperformance." By February 2026, PoPville was referring to it as the closed Target, in a report announcing a UPS Store for 3503 Connecticut next door. In March, PoPville reported that the build-out looked finished and that an April opening was expected. No opening has been confirmed since, so check before bringing a package.

The Uptown Still Has No Announced Use

The Uptown theater in the middle of the block still has no announced plan. Artechouse proposed reusing it as a multipurpose cultural venue for immersive art, performance, and theater. As of July 2026, there had been no news on that proposal since March 2025. In December 2025, the listing agent clarified that the theater itself was not for lease and that only two small storefronts on Connecticut Avenue were available. A July PoPville post floated the idea of an IMAX 70mm theater, but that came from a reader, not from anyone with a project. For now, the outdoor seating going in around the Uptown faces a building with no confirmed future.

The Promenade's Season Has Ended

The block's events show both what the walkway can do and when it does it. Cleveland Park's Night Market ran on the fourth Thursday of each month from April through September on the 3400 block promenade. The final market of the season was September 24. Two weeks earlier, on September 11, Art All Night took its theme from "Art of the Word." It used the promenade, Sam's Park & Shop, the library, and businesses along Connecticut Avenue for music, readings, art activities, and a pet fashion show.

The neighborhood's October calendar mostly takes place elsewhere:

October 17 is a full day. Tregaron Unplugged runs through the early afternoon, and Rosedale's screening starts at 7:10 p.m., so dinner can fit in between. Highlands Tavern's 11 p.m. Saturday close leaves time after the film too. Cleveland Park Main Street's Halloween Bar Crawl on October 30 stops at Atomic Billiards, Taco Cantina, and Nanny O'Brien's, none of them this year's new arrivals.

The promenade's first full year with new tenants is therefore heading into a stretch when the market is over and the patios are cold. Highlands Tavern opened with a rooftop for 60, and Moga's plans call for a 75-seat summer garden. Both bets on the walkway depend on which months the seats stay full. The next evidence will show up on the block itself: an opening date for Over Doughs, signage for Handcraft Donuts, and whether Moga or Club Soda opens before the next Night Market season.

Street-level changes like these can shape how a block feels long before they show up in any price data, and following them closely is part of how Jonathan Taylor Group advises clients on Connecticut Avenue and the streets around it. If you own near the Cleveland Park promenade and want to talk through how its next season might affect your plans, Request a Private Consultation.