Why would the new owners of one of Kittery's most talked-about restaurant buildings hand the lease to someone who already runs three other places in town, instead of bringing in something new to the neighborhood?
That's the quieter story sitting inside the bigger one everyone in Kittery Foreside has already heard: Anneke Jans, the bistro that held down 60 Wallingford Square for twenty years, closed for good in January 2025. The building didn't sit empty for long. It sold this year for $2.49 million, and the space next door at 68 Wallingford Square now belongs to a pizza shop with a name that's new to the sign but not new to the block.
The Room Everyone Still Calls Anneke Jans
Anneke Jans opened in 2005 and spent the better part of two decades serving European bistro fare and small plates at 60 Wallingford Square, becoming the kind of place locals gave directions by. Co-owners Jason Canty and Megan Stewart-Canty closed it permanently on January 12, 2025, after reaching an impasse on their lease renewal with the landlord. It wasn't a story about a restaurant that ran out of ideas or customers. A listing for the building that circulated afterward described the departure plainly: the former tenant had left "for reasons not related to property or business success."
That distinction matters for what came next. A restaurant closing because the food stopped working is a different neighborhood story than a restaurant closing because a lease negotiation broke down. The second kind leaves a building that's still worth buying.
What $2.49 Million Bought at the Cook Block
The building at 60 to 68 Wallingford Square has a name most visitors never hear: the Cook Block, a mixed-use structure dating to 1850 that runs 10,648 square feet along the Piscataqua River, with three commercial units, eight residential units, and a garage. Earlier this year it sold for $2.49 million to James and Mary Weisheit.
James Weisheit put his read on the purchase simply.
"I love the building. I think it's a cornerstone of the Foreside."
The Weisheits moved fast. They leased one of the commercial spaces to a pizza shop almost immediately, according to Mainebiz's reporting on the sale, and were still working to fill a second available unit as of that report. A building that had just lost its anchor tenant of two decades didn't spend the year vacant. It found a new use inside months.
The Same Names Behind Half of Wallingford Square
Here's the part that doesn't show up in a walk down the block unless you already know the names. The pizza shop moving into 68 Wallingford Square is Dudley Street Pizza, launched by Deb and Michael McCluskey. The McCluskeys aren't first-time operators testing out Kittery Foreside. They already run:
- Lil's Cafe
- Salty Spirits
- Henry's Bagel and Deli
All three are already open in Kittery. Dudley Street Pizza is their fourth concept in the same small downtown, not their first bet on it.
That changes what "new restaurant" means in this specific case. The building lost its longest-running tenant, but the space didn't go to an outside chain or a first-time restaurateur betting on the address. It went to operators who had already decided, three times over, that Kittery Foreside was worth building a business in. The turnover at 68 Wallingford Square looks less like a neighborhood in flux and more like a small group of local owners consolidating their footprint on a block they already believe in.
Not Every New Sign Belongs to a Familiar Owner
The Cook Block isn't the only address on the move. A few streets over at 10 Walker Street, Kittery Wine Bar has been under construction with an eye toward a summer 2026 opening. The owners, Katie Howard-Smith and Jody Smith, are building it with help from Howard-Smith's sister Sadie Bell, and their stated concept blends European wine bar energy with a coastal New England setting: wine by the glass, bottle, and flight, alongside shareable snacks.
Unlike Dudley Street Pizza, this one is genuinely new blood. Bell brings years in the New York City restaurant industry, and Howard-Smith's background includes time at the Islington Bottle Shoppe along with in-progress WSET Level 3 wine certification. Two new food and drink businesses opening within walking distance of each other in the same year, one run by owners already embedded in Kittery's restaurant scene and one run by newcomers building their first concept here, says something specific about the block right now. It isn't coasting on nostalgia for what it lost. It's absorbing both continuity and new investment at the same time.
The Festival That Doesn't Care Who's Renting What
None of this turnover has slowed down the event that puts Kittery's food scene on public display every September. The sixth annual Taste of Kittery ran Saturday, September 19, 2026, from noon to 3pm at Post Office Square, bringing the town's restaurant community together for tastings, live entertainment, and the kind of afternoon that draws people who've lived here for decades alongside people who moved in last year.
A festival now in its sixth year isn't dependent on any single tenant's lease. It's built on the idea that Kittery Foreside's food identity is bigger than any one address, which is exactly what the Cook Block's last twelve months have proven in miniature. Anneke Jans leaving didn't end Wallingford Square's relevance as a dining destination. It just meant the next chapter got written by owners who were already writing other chapters nearby.
As of this spring, the Cook Block still had one more commercial space to fill. Whoever takes it will be stepping into a building whose last three tenants tell a consistent story: this corner of Kittery keeps finding its next use before anyone has time to worry it won't.
If you're curious about what else is changing along the Kittery Foreside waterfront, from the Cook Block's remaining vacancy to how buildings like it get valued when they trade hands, the team at Nola & Associates tracks these shifts as part of daily life on the Seacoast, not just as market trivia.
