Above:Market House on the Square Photo: Courtesy of the restaurant
The gently winding streets and gorgeous mansions of Lake Forest recall a lovely Connecticut town. The tony North Shore burg’s history, however, is all-Chicago: Meatpacking magnates Swift and Armour owned estates here. Local starchitects Howard Van Doren Shaw and David Adler designed many of the homes. John Hughes, king of Chicago-set ’80s teen movies, is even buried in its cemetery (more on that below). Oh, and by the way—those winding streets? Planners in the mid-19th century purposefully made them byzantine to help maintain residents’ sense of privacy—which is just a polite way of saying “keep out the riff-raff.”
1. Elawa Farm
The former Armour estate has been reimagined as a 16-acre nature area that features an organic garden, a farmers’ market, cooking classes, and a wildlife center with a bobcat (cool!), a baby sloth (cute!), and a Komodo dragon (no thanks!).
2. Forest Park
This 29-acre lakefront park and beach has swimming cells (between breakwalls that help lessen erosion), a fishing area, and even kayaks and paddleboards for rent. And hey, it just started selling booze!
3. Gorton Community Center
This is no run-of-the-mill rec center: Housed in a historic schoolhouse, it hosts concerts, readings, and art films at the recently renovated John & Nancy Hughes Theater.
4. Herbert Glore House
The only home Frank Lloyd Wright built in Lake Forest is a private residence but welcomes tours occasionally through the Frank Lloyd Wright Building Conservancy.
5. Lake Forest Cemetery
Take a hard left when you pull into the grounds and follow the drive until you see a headstone engraved with “Hughes.” That’s where the legendary filmmaker is buried. Also interred: William H. Smith, who was president of the Associated Press in the 1870s.
6. Lake Forest Book Store
Thankfully, Amazon hasn’t killed this charming independent shop, which has been owned by local women since 1949 and brings in renowned authors such as Georgia Hunter, Chloe Benjamin, and Rene Denfeld.
7. Lake Forest Resale Shop
Do the math: Affluent Lake Forest residents minus stuff they want to ditch equals pretty good swag—mint golf clubs, strappy Gucci sandals, a huge steel and fiberglass replica of a Greek statue …
8. Molly Flavin
It doesn’t get more Lake Forest than this insanely quaint gift shop that stocks colorful candles, crisp linens, and an abundance of flowers.
Family-owned for more than 35 years, old-timey ice cream shop atmosphere, and hand-dipped chocolate-covered Oreos. We’re good.
Just your normal Saturday running-around threads—in posh fabrics like cashmere and velvet.
Eat & Drink
This upscale Mexican joint is almost always packed, and with good reason. Try the ridiculous salmon with a roasted red pepper sauce and ancho-honey glaze.
12. Deer Path Inn
Renovated in 2016, the English manor–style hotel has 57 guest rooms and three restaurants. Stop by for afternoon tea service: The master of tea (it has a master of tea!) comes from a family that’s been involved with the trade since 1842.
13. The Gallery
It’s an art gallery, but it’s also a restaurant with a revolving menu that’s thematically connected to exhibits. Recently: corn dogs, whitefish tostadas, and crème brûlée for a show about Chicago, Havana, and Paris.
14. The Lantern
This throwback burger-and-a-beer place is a favorite spot for retired (and some current) Chicago Bears. Fun game: Find the faded Polaroid of former Bull Toni Kukoč encased along the bar.
15. Market House on the Square
You could shell out $25 for the bistro steak, but locals rave about the $16 double burger with fontina cheese and truffle mayo. And many of the ingredients are locally sourced from the chef’s farm in Sheffield.
April 5:Please your inner cinephile and Francophile with a showing of Faces Places, an Oscar-nominated documentary about an 89-year-old director’s travels through France, at 7 p.m at Gorton Community Center.
April 7:Two things: 1. The Lake Forest Symphony is playing Beethoven at 8 p.m. at Lake Forest Academy. 2. Lake Forest has a symphony?!
April 11:Nosh with authors Stephanie Dray and Laura Kamoie while they discuss their new novel, My Dear Hamilton, during an 11:30 a.m. lunch at the Deer Path Inn. (And yes, it’s that Hamilton.)
April 27 to May 27:Citadel Theatre’s The Explorers Club spoofs British manners, sexism, Victorian adventurers, and who knows what else.
Did You Know?
Jack Benny’s dad owned one of the original shops at downtown Lake Forest’s Market Square, which was among the first planned shopping centers in the United States.
If You Want to Live Here
Median houshold income
Median sale price (house)
(92% white, 4% Asian, 3% Hispanic)
Listing of the month
1126 Edgewood Rd.
Specs:2,189 square feet, 4 bedrooms, 4 baths
This leafy Cape Cod–style house, on two lots, is close to the lake, the high school, and about five bazillion trees.
NOTE: Real estate data are from January. SOURCES: Statistical Atlas, Zillow