Vintage Cars Under the Big Sky

The first time I saw them, I was walking out of Whitefish Lake Lodge on a balmy, late-summer day: vintage cars, three of them, parked in front of the building.

They glimmered like diamonds in the light. They were bright, curvaceous, and cared for like show horses or firstborn children. A small crowd had gathered, and the onlookers were crossing their arms and smiling, rocking back on their heels and shaking their heads appreciatively.

The owners of the cars stood around and beamed, as well. They were jovial, friendly, and thrilled to chat with admirers about the history of their vehicles. Within minutes of interacting with them, it was apparent that these were folks who made a point of exploring often and exploring well. The fact that they did it in beautiful classic cars didn’t hurt, either.

I didn’t know it then, but what I was seeing was a small portion of the Going to the Sun Vintage Car Rally, which winds through Montana every September. One of the most notable vintage car gatherings in the country, the Going to the Sun Rally brings together vintage car aficionados and their masterpieces and takes them on a five-day trip through the stunning landscapes of Montana and Canada. 

This year’s route, for example, snakes from Whitefish, out to Idaho, and up into British Columbia. The roads are scenic and winding, the couples are friendly and enthusiastic, and the cars are jaw-droppingly pretty. Seeing them pass through town is not something you want to miss. 

If you can’t imagine anything better than cruising up Going to the Sun Road or driving through the vineyards of B.C.’s Okanagan region in a classic Porsche, you’re not alone. It’s that kind of excitement the Going to the Sun Rally is dedicated to creating and supporting year after year.

The History of the Going to the Sun Rally

The Going to the Sun Rally started in 2005 when three friends from Bozeman came together with an idea. They shared a love of vintage cars and Montana’s scenic byroads, and they wanted to bring the two elements together.

They also wanted to raise money for charities throughout Montana. After a bit of brainstorming, the vintage car rally was born. The original gathering was small, and the maiden route took rally attendants through Yellowstone and Bozeman, into Whitefish, in the Northwest corner of the state, and through Glacier National Park.

Since then, the rally has become a recurring attraction for many attendants, and several participants come back for the event each year. While some participants own only one vintage car, others own several eligible vehicles and bring a new one to the rally every few years.

Currently, the event admits just 50 teams each year, although it receives about 150 applications annually. Despite the outpouring of interest, the organizers work hard to maintain a balance of about 20% new faces at each gathering. This ensures that vintage car enthusiasts from across the country have the opportunity to participate and supports the spirit of excitement and enthusiasm.

In the years since its inception, the Going to the Sun Rally has become one of the best-known vintage car events in the country. Today, the event brings together enthusiasts from across Canada, Great Britain, and the U.S. Past rallies have included entries from Arizona, California, Connecticut, New York, and Bozeman.

Don’t let the good looks and shiny cars fool you, though: this isn’t just fun and games.

The organizers of the Going to the Sun Rally are dedicated to raising money for charities, and they’ve made that mission a pillar of the event. Since the rally began, it has raised more than $550,000 for Montana organizations and nonprofits, including Big Brothers/Big Sisters, the Clark Fork Coalition, First Descents, Montana Hope Project, Whitefish Legacy Partners, and the Headwaters Trail System.

While the routes are different each year, the focus on local communities isn’t. “We love to go through different communities,” says director Teresa Kessler-Prond. “Before we take off, our directors will go on a pre-rally route to link in with the community and identify needs—things like food banks and educational programs—and figure out how to interface with the community.”

The Current State of the Rally

In 2018, the Rally takes place September 4th through the 9th. Although the Rally commonly starts in the southwestern landscape of Bozeman, they’ll be starting in Whitefish this year. From there, it’s out to Coeur D’Alene, across the border into Osoyoos and Nelson, BC, and then back down to Whitefish, where rally attendants wrap up the celebrations with a closing banquet.

While the Going to the Sun Vintage Car Rally doesn’t announce its locations as it rolls along, you’ve got a pretty good chance of seeing the vintage Porches, Jaguars, and more if you happen to be in or around Whitefish on the September 4th start date. The rally participants gather in Whitefish in the days before the departure date, and it’s not uncommon to see the vintage cars touring around the lake or parked downtown.

If you do happen to find yourself in Whitefish, you may see some of the cars cruising up and down main street or driving back from a day trip to Glacier National Park before the rally kicks off. While you can’t count on it, the rally sometimes announces itself to the local community.

“Once,” says Kessler-Prond, “We were in Crouch, ID. It’s a small community, very quaint. We got in touch with the radio station, and they started to make announcements about car numbers and participants as we were coming into town. People came out to see the cars, and it got to be a fun surprise for the community.”

This year, the rally is supporting Warriors and Quiet Waters, a Bozeman-based organization that works to provide support for post-9/11 combat veterans with fly fishing trips throughout Montana.

While the rally staff has worked for years with this organization, they’re striving to make Warriors and Quiet Waters a more integrated member. In the coming years, they’d like to bring a participating veteran along on the rally with them.

In many ways, this effort is right in line with everything else the rally has done in the years since its launch: a group of dedicated people who come together to celebrate beautiful cars, beautiful places, and, most of all, to support the communities and organizations they believe in.