Boasting scenic charm and boundless amenities, tony Lake Forest is the epitome of the North Shore good life. Here, our essential spots in the lush lakeside community.
Where To Eat
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255 E. Illinois Road, Lake Forest / Website
In a cozy corner of the Deer Path Inn, this award-winning hotel restaurant offers an inviting fine dining menu (think prime beef tartare, roasted duck and wild mushroom risotto) in elegant surroundings. The lavish Sunday brunch buffet has long been a favorite of Lake Forest families, and in pleasant weather, the outdoor space is a special treat.
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293 E. Illinois Road, Lake Forest / Website
This downtown Lake Forest restaurant—part of restauranteur Scott Harris’ beloved Francesca’s empire—boasts zesty, earthy cuisine and friendly service in a space filled with photos of rural Italian life.
See Also: The Ultimate Guide To Evanston
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655 Forest Ave., Lake Forest / Website
Set in Lake Forest’s historic former police and fire department building in the center of town on Market Square, this outpost of the downtown Chicago classic boasts serious personality of its own. With interiors completely renovated and decked in signature Le Colonial style and the restaurant’s signature menu of French-Vietnamese fare, it’s one of the hottest restaurants in town.
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200 N. Field Drive, Lake Forest / Website
Inspired by the ancient white oak heritage trees found in Lake Forest, Oaken Bistro + Bar serves a classic, comforting menu of plates like smoked wings, flatbreads, burgers, salads and pastas. The lounge-style interiors are laid-back and luxurious, and there’s an eclectic list of cocktails, wine and beer.
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181 E. Laurel Ave., Lake Forest / Website
As the co-founders of Ballyhoo Hospitality, husband-and-wife team Ryan and Anna O’Donnell are known for beloved downtown concepts like Gemini Bistro and Coda di Volpe. Now, the partners have expanded their Sophia Steak concept into new territory with their first Lake Forest restaurant, and it’s a huge hit.
Where To Shop
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662 N. Western Ave., Lake Forest / Website
A downtown Lake Forest institution since 1949, this beloved, independently owned book nook has an expansive, meticulously curated selection of tomes and hosts regular author readings and other community events.
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265 Market Square Court, Lake Forest / Website
This long-standing Lake Forest fashion destination exudes more than a century of high style, as it was established by a local socialite after an extravagant shopping spree with Coco Chanel.
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770 N. Western Ave., Lake Forest / Website
This iconic Lake Forest gentlemen’s shoppe has revitalized energy under new owners Tryey Gonzales and Kip Helverson, who curate a smart selection of menswear and accessories from brands like Barbour, Ettinger London and Truefitt & Hill.
260 E. Deerpath Road, Lake Forest / Website
Homemade chocolates, toffee, peanut brittle and more have been the staple of this local family favorite since 1982.
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227 E. Westminster Ave., Lake Forest / Website
Elevated casual womenswear, accessories and gifts are the hallmarks of this style stop with North Shore locations in Winnetka, Glencoe and downtown Lake Forest.
What to See & Do
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1401 Middlefork Drive, Lake Forest / Website
Adjacent to the picturesque trails of the Middlefork Savanna, this restored farm and garden built in 1917 for prominent Chicagoan A. Watson Armour on 16 acres is a lovely spot for year-round strolling as well as shopping fresh produce and flowers in the seasonal Garden Market.
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801 N. Lake Road, Lake Forest / Website
Lake Foresters flock to this 29-acre year-round park for its scenic beach and grass areas, sheltered pavilions, fishing pier, boat launching ramp and walking paths, plus an in-season (Memorial Day to Labor Day) concession stand. Non-resident guest pass $25 daily
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1275 Gilgare Lane, Lake Forest / Website
From 3.65 miles of scenic hiking trails to top-notch birdwatching, self-guided nature exhibits and a stunning lake overlook from a 70-foot bluff, this stately green space is one of the area’s top outdoor destinations.
Western Avenue just north of Deerpath Road / Website
The beating heart of downtown Lake Forest is this historic 1916 square, which was designed by renowned architect Howard Van Doren Shaw, is considered the first planned shopping center in the U.S. and is still the town’s retail hub to this day.
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1260 N. Green Bay Road, Lake Forest / Website
Situated on the lovely Arts & Crafts former estate of architect Howard Van Doren Shaw and poet and playwright Frances Wells Shaw, this renowned artist’ retreat occasionally opens to the public for cultural events such as the Read with Ragdale series, which gives attendees the opportunity to discuss literary works with featured Ragdale resident authors.
Where To Stay
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255 E. Illinois Road, Lake Forest / Website
Inspired by the long-standing tradition of English innkeeping, this iconic property was established in the 1860s and has been one of the area’s top spots for luxury accommodations ever since.
Looking for more luxe Chicago-area guides? See our ultimate Chicago neighborhood guide.
Photography by: Oaken Bistro photo courtesy of Heron Agency; other photos courtesy of brands
