Walk past 269 Market Square Court this month and you'll find M on the Square selling home décor, fresh floral arrangements and gifts under owner Jennifer Mower, who took over the shop earlier this year. Ask around and you'll hear the space carried the M on the Square name once before, under owner Missy Crowe Poth. Before that, it was Molly Flavin's shop. Before that, it was The Trading Post. Three identities and two owners of the current name, all in one address, and if you've lived in Lake Forest more than a decade you've probably shopped there under at least two of them without thinking twice about it.
That kind of turnover isn't a symptom of anything wrong with Market Square. It's the point. The Square has been swapping out what's behind its doors since 1916 while doing the exact same job for the town the whole time, and once you notice the pattern at M on the Square, you start seeing it everywhere else on the block too.
A Design Built to Outlast Any One Tenant
Market Square wasn't planned as a strip of shops that happened to end up next to each other. In 1913, real estate developer Arthur Aldis assembled a group of Lake Forest residents to buy out a stretch of buildings across from the train depot and hired architect Howard Van Doren Shaw, working with Edward Bennett, to lay out a U-shaped block wrapped around a landscaped green, with parking built into the perimeter from day one. It opened in 1916 as one of the first shopping districts in the country designed specifically around the automobile, and the layout has barely moved since.
The clearest proof that the design outlasts the retailers is the single most visible storefront in the whole complex, the one facing directly across from the train station where every commuter's eye lands first. It opened as First National Bank. Marshall Field's took the space over in 1931 and ran its very first branch location there. When Macy's absorbed Field's, the storefront went along with it, and Macy's closed that location in 2008. The most prominent address in Market Square has now changed identity at least three times in a century, and the Square itself never stopped functioning as the town's front door for a single one of those transitions.
M on the Square's own history, three identities and a change of ownership under the current name, is the same story at a smaller scale. The shop changes. The corner doesn't.
What's Actually Open Right Now
Not every storefront turns over at the same rate, and the contrast is worth naming. Kiddles Sports has been outfitting Lake Forest for cycling and athletics since 1968. The Lake Forest Shop is a third-generation, family-owned clothing store that's been running since 1922, started by Margaret Baxter Foster. Williams-Sonoma and Forest Bootery round out the anchor tenants that have held their spots long enough to become fixtures rather than businesses. Against that backdrop, a boutique like M on the Square passing through three identities and a change of hands in the same footprint reads less like instability and more like the Square doing what it was designed to do: hold the block steady while whatever's trending in home goods or apparel cycles through underneath it.
A block off the Square, the Left Bank hot dog stand has been serving Chicago-style dogs and what regulars call its "not-so-sloppy joes" since 1963, without ever changing hands. It's the version of continuity that doesn't rely on the building's design at all, just a small business that decided sixty-plus years ago what it was going to be and never renegotiated.
The Calendar Nobody Interrupts
Whatever the retail mix looks like in any given year, Market Square runs its own events calendar independent of which name is on which lease. That calendar isn't slowing down. Lake Forest Day, sponsored by American Legion McKinlock Post No. 264, brought its parade and carnival through town on August 5, 2026. The Square's Summer Sounds live music series has been running through the season on the green itself. A few blocks away, the Gorton Center has The Brothers Doobie booked for August 20. And the volunteer-run Lake Forest Music Festival, staged in the parking lot behind City Hall with two stages, four live bands and a bourbon, beer and wine pavilion alongside the barbecue, keeps the late-summer stretch full before the calendar turns toward BOO in the Square in October and Joy & Wonder once the holidays arrive.
None of those events depend on M on the Square being M on the Square, or on Kiddles staying Kiddles, or on whatever eventually leases the old Macy's footprint. The programming was never tied to the tenant roster. It was tied to the green space and the town's habit of showing up for it, which is exactly what Aldis and Shaw built into the plan in 1916 whether they used that language or not.
Why This Is the Detail Worth Knowing
If you live within walking distance of the Square, the practical takeaway isn't which shop to visit this weekend. It's that the shop you visit this weekend is not a fixed feature of the neighborhood, and that's fine. The building holding it has already outlived a bank, a department store flagship and two prior identities above M on the Square's own door, and it will very likely outlive whatever's currently trading there too. What doesn't turn over is the green, the parking laid out around it in 1916, and the calendar of parades, concerts and festivals that the town keeps running regardless of who's leasing space that season.
That's the part worth carrying with you the next time a familiar storefront swaps its sign. It's not a sign the neighborhood is changing underneath you. It's the neighborhood working exactly the way it was designed to a hundred and ten years ago.
Cara Buffa has spent more than thirty years paying attention to the details that make Chicago's neighborhoods and North Shore suburbs work, the kind that don't show up in a listing description but explain why people stay. If you're curious about Lake Forest or any of the communities Cara Buffa covers, reach out and work directly with Cara for a personal conversation about the area.
