Walk down Walker Street in Kittery Foreside on a Thursday evening now and you will pass a lit window where a children's clothing shop used to be. Inside, people are leaning over a bar with a wine list on a chalkboard and small plates coming out of a kitchen that did not exist a year ago. It looks like the kind of opening that happens constantly in a coastal town this size. It is not. It is the last open storefront on one specific block finally getting filled, closing out a project that started well over a decade ago.
That distinction matters if you live here, because it changes what you should expect to see next.
One Block, Not a Neighborhood
Wallingford Square is not a neighborhood in the way people usually mean it. It is technically one block, running from Government Street to Walker Street and ending at the Shipyard entrance. Everything people mean when they say Kittery Foreside has "come alive" over the past decade has largely happened on that single stretch of pavement.
It started in 2013, when Michael Landgarten, one of three investors who bought and renovated 7 Wallingford Square, took on the largest building on the block. The idea did not come from a developer's plan. It came out of a neighborhood block party that Landgarten had helped organize with Janice Grady, after a fellow Foreside resident mentioned the building was for sale.
What happened next was not organic growth in the usual sense. According to Lil's Cafe, whose own account of its founding lays out the sequence, the businesses at 7 Wallingford Square were opened in a deliberate order: first Folk gallery, then Anju Noodle Bar, then Maine Squeeze juice bar in a converted drive-up bank kiosk, and finally Maine Meat. Each new lease was chosen to complement what was already there rather than compete with it. A coffee and pastry stop next to a noodle bar next to a butcher shop next to a wine and cocktail counter is not an accident. It is a deliberate mix of businesses.
The Walk You Can Do Now
With Kittery Wine Bar's opening this summer, the mix that started at 7 Wallingford Square now stretches into a full evening without moving your car.
| Stop | What it is | Address |
|---|---|---|
| Kittery Wine Bar | Wine and small plates | 10 Walker St |
| The Wallingford Dram | Craft cocktail bar | 7 Wallingford Square |
| Anju Noodle Bar | Asian noodle restaurant | 7 Wallingford Square |
| The Black Birch | American gastropub | 2 Government St |
| Lil's Cafe | Cafe, bakery, vinyl shop | 7 Wallingford Square |
| Maine Meat | Butcher, wine, and beer shop | 7 Wallingford Square, #106 |
| Folk | Gallery and gift shop | 7 Wallingford Square, #103 |
Start at Folk to pick up a gift, cross to the Dram for a cocktail, sit down at Anju for noodles, then finish two doors over at the wine bar. None of that requires a car, and none of it requires leaving Wallingford Square. That was the point of building it this way in the first place.
Same Family, More Doors
The newest addition before the wine bar was not new to the block's ownership pattern either. Salty Spirits opened in Kittery Foreside under Deb and Michael McCluskey, who also run Lil's Cafe and Henry's Bagel and Deli in town. It is the same small group of owners extending their footprint rather than a new operator testing the waters. If you have eaten a pastry at Lil's, there is a decent chance the people behind your cocktail at Salty Spirits are the same ones who hired the baker.
That pattern, a handful of owners expanding sideways into adjacent storefronts instead of a wave of unrelated newcomers, is a big part of why the block feels cohesive rather than like a strip of businesses that happen to share a sidewalk.
The Last Vacancy Belonged to a Children's Clothing Store
The wine bar's arrival breaks that pattern in one specific way, and it is worth sitting with because it tells you something about how this block actually fills in. The space at 10 Walker Street was, until January, home to Kit & Co., a children's clothing store. When that shop closed, the storefront sat empty for roughly six months before Kittery Wine Bar's grand opening this July.
The people who filled it are not part of the McCluskey group or the original 2013 investors. Katie Howard-Smith and her husband, Jody Smith, relocated to the Seacoast during the pandemic. Howard-Smith spent nearly two decades in journalism and media sales before retraining in wine retail and education, and her sister, Sadie Bell, brought experience from New York City's restaurant and bar industry to help get the place open. They told Mainebiz they prioritized hiring Seacoast residents and sourcing from Maine farmers and producers, the same local-first instinct that shaped the block a decade earlier, just arriving through a different door.
The bar is open Thursday through Saturday from 4 to 10 p.m., and Sunday from 11 a.m. to 3 p.m., which makes it one of the few spots on the block with a genuine daytime Sunday hour, useful if you are walking off a weekend errand at the Foreside Bike Shop and want somewhere to sit down before noon.
What's Next on the Same Block
With the wine bar open, there is no obvious empty storefront left on Wallingford Square proper. That does not mean nothing else is coming to the immediate area. A few steps away, The Dance Hall has announced its 2026 Jazz Casual season, with Sunday shows running from late September through the end of November. It is the kind of recurring, low-key programming that gives the block a reason to fill up on a weeknight well after the summer outlet traffic thins out.
But the practical takeaway for anyone who lives nearby is simpler than a forecast. The block that people mean when they talk about Kittery Foreside's food and drink scene is one block, built by a small number of owners who treated each new lease as part of the same plan, and it is, for the moment, full. The next storefront to open with any real buzz is more likely to show up on Government Street or further down Walker, not on Wallingford Square itself, because there is nowhere left on the square to put it.
If you want the short version for tonight: cross Government Street, grab a stool at the Dram, walk two doors down for noodles at Anju, and finish at the new wine bar on Walker before it closes at 10.
Curious what else is changing in Kittery or across the Seacoast? Williams Realty Partners keeps a close eye on the towns we live and work in, storefront by storefront. Let's Connect if you ever want to talk about what's happening in your corner of Southern Maine or the Seacoast.
