Walk the north side of Market Square this month and you'll pass a window that wasn't there a year ago. Free People opened in February 2026, tucked into a storefront a few doors down from Lululemon and Starbucks, according to reporting in Lake Forest High School's student paper, The Forest Scout. It's a bohemian, younger-skewing label in a shopping center that turns 110 this year. Both facts fit together, and the way Market Square was built explains why.
Most write-ups of Market Square stop at the history: opened in 1916, designed by architect Howard Van Doren Shaw with local developer Arthur T. Aldis, commonly cited as the first planned shopping center in the country. That's true and worth knowing. But the history explains something more useful than trivia. It explains why a center old enough to have a National Register listing can absorb a store aimed at teenagers without missing a step, and why a family-run shop that opened when Warren Harding was president is still standing two doors down.
The Design Choice That Makes Turnover Normal
Shaw didn't build one big building with one big anchor. According to the architectural record maintained by SAH Archipedia, the ground level of Market Square holds roughly thirty separate storefronts arranged around a landscaped green, each with its own narrow frontage and minimal signage. That's the whole trick. A shopping center built around thirty small leaseholds doesn't live or die with any single tenant. One storefront can turn over to a new retailer while the one next to it hasn't changed hands in decades, and neither shift threatens the character of the place.
Compare that to a mall built around two or three department store anchors, where a single closure reshapes the entire property. Market Square was never built that way. At roughly 103,000 square feet total, per Wikipedia's entry on the property, it's a fraction of the size of a regional mall, but it was designed to spread risk across dozens of small commitments rather than concentrate it in a few large ones. That structural choice from 1916 is the reason the square can look almost frozen in time and still be actively changing underneath.
What Just Changed
Free People is the newest example, but it's not the only one. In February 2026, the Lake Forest-Lake Bluff Chamber of Commerce ran a short profile on M on the Square, the home décor and floral boutique on the green, introducing its new owner, Jennifer Mower. The shop itself isn't new. Mower described a lineage that runs back through The Trading Post, then Molly Flavin's, then Missy Crowe Poth's version of M on the Square before landing with her.
"I have always loved this store dating back to when it was The Trading Post then Molly Flavin's shop and finally Missy Crowe Poth's M on the Square," Mower told the Chamber.
That's the pattern worth noticing. The storefront hasn't moved. The category hasn't moved. Home décor and gifts have occupied that particular lease for years under a rotating cast of owners, each one taking over a going concern rather than starting from empty space. It's turnover that looks, from the sidewalk, like continuity.
Free People's arrival works the same way in reverse. The Forest Scout's coverage noted that before Free People signed on, Starbucks and Lululemon were the only stores in the square aimed squarely at a younger shopper, and that the absence of national apparel brands aimed at teenagers had been sending some local shoppers toward Old Orchard in Skokie instead. One new storefront changed that math without displacing anything else on the green.
What Hasn't Turned Over, and Why That's the Other Half of the Story
Set the new arrivals against the tenants that have simply never left. The Lake Forest Shop has operated as a family-owned clothing store since 1922, when it started as Margaret Baxter Foster selling pieces out of her own closet, according to reporting from Islands.com. It's now in its third generation of family ownership. Kiddles Sports has anchored a corner of the square since 1968. Left Bank, the hole-in-the-wall known for Chicago-style hot dogs and its own take on a sloppy joe, has served the same corner since 1963. Local reporting notes that Lake Forest native Vince Vaughn has counted himself among its regulars over the years.
None of those three businesses needed to reinvent themselves to survive alongside a wave of newer arrivals. Le Colonial, the upscale Vietnamese restaurant chain that started in New York in 1993, opened its Market Square location in 2022, giving the square a different kind of dining option than Left Bank's counter service, without either one crowding out the other. A shopping center with thirty separate leaseholds has room for a 103-year-old family shop and a three-year-old imported restaurant concept at the same time, because neither one was ever competing for the same square footage.
Here's the current tenant mix if you're mapping the square in your head:
- Decades-old, family or independently run: The Lake Forest Shop (1922), Left Bank (1963), Kiddles Sports (1968)
- National retail, longer-standing: Talbots, Williams-Sonoma, J. Crew, J. McLaughlin, Forest Bootery
- Recent arrivals: Le Colonial (2022), Free People (2026)
- Recently changed hands, same category: M on the Square (2026, new ownership under Jennifer Mower)
That's not a museum. It's a small, working commercial district where the churn rate is low enough that each individual change gets noticed by name, which is a very different experience from watching a strip mall's tenant roster shuffle every eighteen months.
The Details Easy to Miss on a Fast Walk-Through
The green at the center of the square carries its own layer of history that has nothing to do with retail. The fountain at the east end is topped by a sculpture called "Girl with Baby on Shoulder," created by Sylvia Shaw Judson and installed in 1982, according to the Cultural Landscape Foundation. Judson was Howard Van Doren Shaw's daughter, which means the person who designed the square's buildings and the person who made the piece that anchors its green were father and daughter, separated by more than sixty years. It's the kind of detail that doesn't show up on a store directory but changes how a five-minute pass through the square reads if you know it.
A block off the square sits the 1933 Art Deco post office, easy to walk past if you're headed straight for a parking spot but worth the detour for its high ceilings and original counters. None of this requires planning a special trip. It's simply what's there if you slow down on a walk you'd otherwise make on autopilot.
A Reason to Stay Past Dinner
If you're already planning an evening at the square this fall, the History Center of Lake Forest-Lake Bluff has two programs on the calendar worth building an evening around: one on September 17 and another on October 8, both at 7:00 p.m. Either one pairs naturally with dinner at Le Colonial beforehand or a hot dog at Left Bank if you'd rather keep it simple, and both put you back on the green in time to see the fountain lit for the evening.
None of this requires treating Market Square as a destination you have to plan around. It's already part of how Lake Forest runs its week. The point of noticing the turnover this fall isn't that the square is changing dramatically. It's that a shopping center built in 1916 was designed well enough to keep changing in small pieces for over a century without ever needing to change all at once.
If you're weighing what a specific home near Market Square is worth in today's market, or just curious how walkable retail like this factors into value on the North Shore, Jennifer Haug can walk you through it, no obligation required.
