Aug 24, 2023 - Things to Do

A day tripper's guide to historic Sheridan Road

Photo of a walkway with plants and signs for businesses
Lake Forest. Photo: Justin Kaufmann/Axios

For my money, the best quick getaway in any season is to head north along Lake Michigan on historic Sheridan Road.

  • Drive it. Bike it. Hell, you could even walk it.

๐Ÿ˜๏ธ Catch up quick: The famed road (our Highway 101) was built in the late 19th century as an extension to Lake Shore Drive.

  • The scenery is spectacular, including the massive homes you see on the lakefront.

The road technically starts in Chicago, but the sights start when you hit Evanston and continue all the way up to Zion and Illinois State Beach Park (about 50 miles).

  • You could continue up to Wisconsin, but we didn't go that far for this trip.
Photo of a counter inside a cafe.
Hometown Coffee & Juice in Glencoe. Photo: Justin Kaufmann/Axios

๐Ÿฅค Breakfast: There are so many options in Evanston, Wilmette and Winnetka, but we stayed the course until Glencoe to stop at Hometown Coffee and Juice.

  • They have an extensive menu of bowls, smoothies and toasts that attract North Shore residents from all over the lakefront.

Mid-morning activity: Getting to the lake is a little tough on the North Shore, given that most municipalities guard their beaches. But Fort Sheridan is a nice spot to take in nature and the shoreline.

  • You also get a history lesson on how the military trained pilots and artillery units.
  • For a pit stop just south of Glencoe, you could get a tour of Baha'i Temple in Wilmette.
Photo of an old artillery gun pointed at a lake.
Artillery still on display along the bluffs of Lake Michigan at Fort Sheridan Forest Preserve. Photo: Justin Kaufmann/Axios

๐ŸŒญ Lunch: Keep going north to Lake Forest to check out Left Bank. The 60-year-old hot dog stand is also known for its "Not So Sloppy Joe," a hollowed-out kaiser roll stuffed with meat, cheese, onion and pickle.

  • Great taste, less mess.
Photo of a sandwich in a red basket.
Left Bank in Lake Forest. Photo: Justin Kaufmann/Axios

๐Ÿ˜Ž Afternoon activity: You could stay in Lake Forest and browse the quaint storefronts, home to a variety of fair trade stores and consignment sellers.

  • Or go house-gawking, to see everything from picket fences to gaudy mansions.

To get out of town, go north to Zion, where the state park beach is free.

Dinner: So many options.

  • I like to hit Highwood (just south of Fort Sheridan) for La Casa de Isaac & Moishe or any other dining spot there.
  • Or if you want to go fancy, Aboyer in Winnetka is a local favorite.

๐ŸŒƒ Evening activities: You can head to Highland Park and see a show at Ravinia, which has Boys II Men this weekend. Or explore any other of the gorgeous cities on the North Shore.

Editor's note: This story has been corrected to reflect that Aboyer is in Winnetka, not Kenilworth, and Ravinia is in Highland Park, not Glencoe.


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