America's First Planned Shopping Center Is A Historic Midwest Mecca Of Design, Boutiques, And Eats

Chicago's North Shore is lined with wealthy suburbs filled with malls and boutique shops, but only one place holds the distinction of being home to America's first planned shopping center. When Market Square opened in downtown Lake Forest in 1916, there wasn't anything else like it in the United States. Modeled after English market squares, this U-shaped shopping center stood out for its pioneering approach to urban planning. It was one of the first commercial hubs to be planned around automobiles, with parking spots bordering the shops, and it is cited as one of the first strip malls, too.

Market Square design offers a charming mix of European styles: Flemish, English, and Bavarian elements come together in brick and limestone buildings, while an ornate clock tower and sundial arguably influenced the architecture of outdoor malls for years to come. Tree-lined walkways with benches surround a small park with a fountain and sculptures, making Market Square a strong contender for the best outdoor malls for the ultimate shopping experience.

Market Square embodies another time and place and a slowness outside the fast-paced life in Chicago, just over 30 miles away. Take a leisurely stroll to explore its historic 20th-century boutiques or stop for a classic Chicago hot dog at a Lake Forest institution. For over a century, Market Square has been an iconic North Shore destination. 

While Lake Forest may now be one of the Midwest's wealthiest suburbs, in the 1860s, it was more like an Old West town. Things changed when Chicago's elite started building their summer homes in this forested area along the shore of Lake Michigan. In 1912, local real estate developer Arthur Aldis partnered with architect Howard Van Doren Shaw to build a proper downtown for the up-and-coming Lake Forest. 

They created Market Square, whose three-sided layout of commercial and residential spaces opened out onto the train station, so that when commuters got off the train, it was the first thing they saw. It also helped that Market Square had such a strong design to draw people in. In fact, it's one of the state's best examples of the European revival style that became popular in the early 20th century. Elements like the division of storefront windows into smaller panes offered a fresh perspective to the shopping experience, a contrast to traditional commercial districts at the time.

Although online shopping has created so many abandoned malls around America, Market Square's retail power has stood the test of time. Initially, it was business and service-oriented. Its original clients were the First National Bank, U.S. Postal Service, and the YWCA, but it started shifting to retail in 1931 when Marshall Field & Company moved in. Brands like Kiddles Sporting Goods followed, and this 1968 athletic shop still stands today as a fixture of Market Square. Other historic Market Square boutiques include Lake Forest Shop, a third-generation family-owned clothing store that's been open since 1922, when the Coco Chanel-loving Margaret Baxter Foster started selling items from her overflowing closet. Besides these local shops, there are also bigger retailers like Williams-Sonoma and Free People.

After working up an appetite from shopping, you may want to head to Left Bank, a local institution known for its Chicago-style hot dogs and "not-so-sloppy joes." This hole-in-the-wall joint opened in 1963 and has been serving folks from all walks of life since. People like Lake Forest native Vince Vaughn have been known to grab a seat in its small seating area to enjoy what one Google reviewer calls the "best dogs in Chicago."

If you prefer a more upscale vibe, check out Le Colonial Lake Forest, a high-end Vietnamese restaurant chain that first began in New York City in 1993. This location opened in 2022, and visitors can enjoy lunch or dinner on its patio, terrace, or indoor dining room. The menus include Vietnamese dishes like crunchy green papaya salad, bo luc lac (shaking beef), and bo bia (vegetable rolls).

Getting to Market Square is a breeze since it was designed with different forms of transportation in mind. There are two-hour parking spots surrounding the shopping center's park. Additional 90-minute and three-hour spots are all around the area. Or you can take the UP-N train for an hour from Chicago, which leaves you right across the street from Market Square. That way, you can also see the historic 20th-century train station, whose English Tudor style inspired the architecture of Lake Forest's iconic shopping plaza.