Above: Ravinia Festival Photo: Courtesy of Ravinia Festival
Railroad magnate and former Chicago mayor Walter S. Gurnee kept it literal when he named Highland Park in the 1850s: The land was in a park that sat on a 100-foot-high bluff overlooking the lake. Now the North Shore burg is better known for Ravinia, the über-classy outdoor music venue, and its lively downtown, which boasts both well-curated boutiques and bourgie chains such as Anthropologie and Eileen Fisher. Then there’s the 385-acre Chicago Botanic Garden, which is technically in Glencoe but just across the street from Highland Park. This month gives you two reasons to visit: abundant spring blooms and the return of the wildly popular Antiques, Garden and Design Show (April 15 to 17), featuring dealers from San Francisco to Surrey, England.
1. Ben Rose House
AKA the Ferris Bueller house, where best bud Cameron lived in the John Hughes classic. You can peek at the glass-walled hideaway, designed by Mies acolyte A. James Speyer, from the end of the driveway. 370 Beech St.
The famed architect’s surprisingly modest bungalow is on the National Register of Historic Places. (No tours, though.) 950–954 Dean Ave.
4. Rosewood Beach
After a $14.5 million revamp, this gorgeous stretch of sand features winding walking paths and an elegant science center. (Cover the kids’ eyes: Lake fish will hit the adjacent Ravinia Stream this month to spawn.) pdhp.org/rosewood-beach-project
5. Stupey Log Cabin
And you thought microapartments were bad: A family of 10 originally crammed into this 1847 one-room log cabin, the oldest standing building in town. highlandparkhistory.com
How’s this for cute: The tot shop has a mini ball pit, an electric train set suspended from the ceiling, and “toyologists” to help find the right playthings. beanstalktoys.com
7. Rock N’ Rags
Business in the front (women’s clothing and jewelry). Party in the back (albums and CDs). shoprocknrags.com
8. Shaevitz Market
Chicago dining editor Penny Pollack gets her holiday brisket here. Order at least two weeks ahead! shaevitzkosher.com