By Damien Jaques Senior Contributing Editor Published Jul 04, 2011 at 9:01 AM

Warm summer nights, a newly issued driver's license and keys to the family car. It's 1963 or '64, and some of us Milwaukee kids on the leading edge of the Baby Boom are a little bored and restless.

Summerfest was a word and a concept yet to be coined. Large rock concerts were rare and never happened in Milwaukee. A television was the most sophisticated electronic device we owned.

A full tank of gas meant an evening road trip to The Kiltie in Oconomowoc, a drive-in restaurant that made its own frozen custard. For a car full of teenage boys, the food was the secondary attraction. The Kiltie had carhops who wore teasingly short Scottish plaid skirts.

Nearly 50 years later, Milwaukee teens don't need to travel for entertainment but carhops are still at The Kiltie, hanging aluminum trays bearing burgers, sundaes and malts on car windows. A note to the guys: those plaid skirts are still pleasingly short. Carhops report they are often asked for their phone numbers.

In fact, a visit to The Kiltie in 2011 reveals amazingly little has changed. The restaurant got a new owner, Drew Howie, 20 years ago, but that had virtually no effect on the drive-in's look, menu and operations. A 1973 graduate of Oconomowoc High School, Howie had begun working at The Kiltie as a teenager.

The Kiltie's refusal to acknowledge the passage of time accounts for much of its charm. From the logo of a smiling Scotsman wearing a Tam o' Shanter hat, to the large neon The KILTIE sign, to the lack of a microphone-speaker system for customers to voice their orders, The Kiltie is still in the '60s.

"We thought speakers were too impersonal," Howie explains when asked why that update to drive-in technology was never installed.

The Kiltie has also not bowed to the flavor-of-the-day trend made popular at other custard eateries. On weekdays it offers only chocolate, vanilla and a twist of the two. Limited special flavors such as mocha and mint are available on weekends.

The retro feel at The Kiltie extends to the staff, which numbers about 50 part-timers. Carhops have been known to pack water guns on especially hot days, and Howie, sort of a favorite uncle figure, encourages high-spirited fun.

When business is slow, staffers have tossed around footballs and frisbees. Parking lot races have broken out. Howie is also committed to his employees on a more serious level.

Manager Kristen Hilbert, who has worked at The Kiltie for eight years, says, "Drew treats us like we were his kids. He always says family, school and sports come first."

When her car went to a repair shop for an extended period of time, he loaned Hilbert one of his.

The loyalty works both ways. A teen can begin working at The Kiltie at 14, and employees often stay for eight to 10 years.

Brittany Sontag, who will be a senior at UWM in the fall, works as a server at the Water Street Brewery during the school year, but she drives out to Oconomowoc to do carhop shifts at The Kiltie in the summer. While the money is good, she credits the atmosphere for her continued presence there.

High school reunion programs from area schools often include a visit to The Kiltie, and wedding parties have stopped there between the church and the reception.

The restaurant has a shorter season than most drive-ins because it is reliant on customers who have summer lake homes in Waukesha County. When those folks remove their piers and lock up their houses, business diminishes. The Kiltie opens in early April and closes in mid-September.

In keeping with its '60s persona, The Kiltie has no website, but a Facebook fan page exists. The drive-in's address is N48 W36154 Wisconsin Ave., Oconomowoc.

Details of The Kiltie's history are murky. Howie believes his restaurant dates back to 1947 or '48, and local lore is that the founder was a Scotsman. Why else would he name his restaurant The Kiltie?


Damien Jaques Senior Contributing Editor

Damien has been around so long, he was at Summerfest the night George Carlin was arrested for speaking the seven dirty words you can't say on TV. He was also at the Uptown Theatre the night Bruce Springsteen's first Milwaukee concert was interrupted for three hours by a bomb scare. Damien was reviewing the concert for the Milwaukee Journal. He wrote for the Journal and Journal Sentinel for 37 years, the last 29 as theater critic.

During those years, Damien served two terms on the board of the American Theatre Critics Association, a term on the board of the association's foundation, and he studied the Latinization of American culture in a University of Southern California fellowship program. Damien also hosted his own arts radio program, "Milwaukee Presents with Damien Jaques," on WHAD for eight years.

Travel, books and, not surprisingly, theater top the list of Damien's interests. A news junkie, he is particularly plugged into politics and international affairs, but he also closely follows the Brewers, Packers and Marquette baskeball. Damien lives downtown, within easy walking distance of most of the theaters he attends.