Built in 1929 as a weekend retreat for wealthy Chicagoans, the Deer Path Inn has retained its charms—and can now be enjoyed by the somewhat less privileged.
Built in 1929 as a weekend retreat for wealthy Chicagoans, the Deer Path Inn has retained its charms—and can now be enjoyed by the somewhat less privileged. Credit: Mara Shalhoup

I likely would never have had the occasion to visit Lake Forest—that “bastion of gentility and reserve“—if not for the gravitational pull of the town’s annual rummage sale.

I’ve spent an inordinate portion of my adult life scouring secondhand stores and junk shops for the likes of vintage purses (I recently unearthed a Coach shoulder bag at the Village Discount Outlet on Kedzie), midcentury china (I once scored an eight-piece set of Russel Wright serving platters at a yard sale), and long-lost oil paintings by 17th century masters worth 100 times my lifetime earnings (impossible, sure, but that doesn’t mean I’ll stop trying).

So I was easily swayed to travel to Lake Forest for a rummage sale billed not only as among the highest-grossing in the country, but one that’s filled with castoffs from some of the country’s highest-grossing households. I was so compelled, in fact, that I woke up at 7 AM on a Saturday to book it for the burbs.

Two bags of clothes, three massive brass planters, and $85 later, I could have departed Lake Forest perfectly content. Then I got slightly lost and happened upon an ivy-clad, Tudor-style relic: the Deer Path Inn, designed in the 1920s by architect William C. Jones (who also worked on the 1893 World’s Columbian Exhibition) as a weekend retreat for upper-crust Chicagoans.

I ended up leaving Lake Forest ecstatic.

The thing about the inn that initially gave my shopping companion and me pause, aside from its charming facade, was a side entrance shaded by a green awning that enticingly announced in Old English lettering: “The Bar.” We hesitated only for a moment, concerned that my ratty Chuck Taylors and stained T-shirt would offend the staff and guests of such a fine establishment. Of course, a solution was near at hand. I extracted from my rummage sale loot a cable-knit Land’s End sweater and lime-green, butter-soft Italian loafers. The transformation into prototypical Lake Forestonian was instantaneous.

The bar wouldn’t open for another hour. Fortunately, the inn’s English Room was still serving lunch. My friend and I lazed away the remainder of the afternoon gazing upon the misty, moody courtyard; nibbling on lobster salad and chicken Milanese while sipping martinis; and poking our heads into the Deer Path Inn’s every nook and cranny.

The bar, once it opened, was all we’d hoped it would be, the walls hung with oil paintings of hunting dogs and the ceiling dripping with chandeliers. And a concierge was kind enough to provide us a glimpse of a room—a suite with its own fireplace. (Though nice, I’d have been fine with one of the more basic options.) It was like being transported to another time—and another caste.

We decided it would be worth returning to the inn this summer to spend the night, for several reasons. First, the Metra will take you straight to Lake Forest, but not before passing by the Chicago Botanic Garden. That means you could stop off in Glencoe and spend the afternoon walking the 2.6-mile perimeter of the grounds and revisiting childhood in the model railroad garden: 18 miniscule trains running on 1,600 feet of tracks, past tiny replicas of 50 American landmarks including Wrigley Field, Old Faithful, New Orleans’s French Quarter, Frank Lloyd Wright’s Robie House, and the Golden Gate Bridge.

Yet another bucolic wonderland can be found a mere 15-minute walk from the Deer Path Inn: the Skokie River Nature Preserve. June is an especially fine time to visit the 122-acre site; both the Shaw Prairie and Bennett Meadow, popular spots for hikers and bird-watchers, are graced by more ephemeral guests: scores of butterflies, from viceroys to pearl crescents, fritillaries to swallowtails.

The third destination proximate to the inn, a three-minute Metra ride north in Lake Bluff, isn’t just a dining destination worthy of a trip should you happen to be in the northern suburbs. It’s a dining destination worthy of the trip, period. At Inovasi, chef John des Rosiers (a veteran of Charlie Trotter’s and Gabriel’s) has composed a menu of dishes with smartly sourced ingredients—Anson Mills polenta, Q7 Ranch beef, Meadow Haven Farm chicken—and entrees that top out at $22. But you might as well spring for the six-course tasting menu with beer and wine pairings. This is the high life, after all.