Twisted Road has never had an office. I started the company with a folding chair and card table in my kids’ playroom. Then, later, as I hired people to keep up with the demand, we decided against an office. It seemed too structured. Too corporate. And it wasn’t us.

So with employees in five states, it’s been difficult for us to get to know each other. I mean, we use Slack at all hours of the day—and night!—but having some personal contact is just better than shared memes and Zoom calls.

It was time to schedule an offsite.

How the Ice Age & Dairy Farms Made Our Choice Easy

Picking a central location with good riding proved to be a little bit of a challenge. You see, our front-end developer Chris didn’t have his motorcycle endorsement, so he couldn’t rent with us. Which meant that we had two choices: Chris either had to get his endorsement quickly, or we needed to ride near Chris—in Kansas City. And, because people don’t see Kansas City as the riding capital of anywhere, he really needed an endorsement. 

So after riding for 21 years, he finally made his way to the DMV on April 27, 2021 for his road test. After witnessing the rider before him drop his bike during the exam and still pass, Chris also passed. For the purpose of our trip, we appreciate Kansas’s loose standards (which were also apparent on Chris' original license which had him listed as "female"). 

With our team spread out between Chicago, Denver, Austin, Indiana, and Kansas City, we wanted something that was equally (in)convenient for everyone. We decided to ride the Driftless Area, which encompasses the corners of Wisconsin, Illinois, Iowa, and Minnesota. Many of you know the midwest for having straight flat roads. There’s even the moto-joke “What’s the difference between riding the Tail of the Dragon and riding in Chicago? The Tail of the Dragon is 318 turns in 11 miles, and riding Chicago is 11 turns in 318 miles.” But the Driftless Area is different.

You see, the entire Midwest was flattened by glaciers during the last ice age, but not the Driftless Area. So this area is known for “steep, forested ridges, deeply carved river valleys, and geology-characterized by spring-fed waterfalls and cold-water trout streams.” Thanks Wikipedia. In addition to these hills and twisties, there are plenty of dairy farms in the area, so local roads are kept in pristine condition to allow milk trucks and other vehicles to safely navigate the region, regardless of weather conditions. So even though there aren’t many vehicles in the area, the roads are very well maintained. 

Rolling hills, plenty of turns, pristine roads with few cars—the perfect antidote for long workdays.

Our Moto Trip-Planning Resources

The team trickled into the Windy City throughout the weekend. Some brought spouses so they could explore the Chicago area together. Others came alone, for a break from kids and exes. Our freelancers and even our star intern joined that evening for dinner and laughs around a fire pit (bundled, because Chicago).

Tuesday morning, we got our bikes. I rode my 2013 Moto Guzzi Griso, and head of marketing Sean took Jason’s Africa Twin. Community manager Nick and Chris grabbed Harleys from Woodstock Harley Davidson. Nick was on a 2019 Harley Heritage Classic, and Chris was on a 2019 Harley Street Glide Special. Community manager Clare doesn’t ride, but she rented this 2021 maroon Nissan Sentra from Enterprise, and generously helped us transport our luggage and groceries.

I used two resources to plan the ride. First, Driftless Road Adventures gave me plenty of routes to try out. Because we stayed in SW Wisconsin, the Pecatonica Route was best suited for us. I then used The Rever app to import these roads and help us navigate during our rides.

Eating & Riding—Hallmarks of a Good Trip

Once the bikes were picked up, we rode to our Airbnb, a working farm in Monroe, Wisconsin where we met Dan. He’s been working on the farm his entire life, and he was eager to answer our many questions about the cattle, horses, a single, fat pig, and other livestock.

For dinner the first night, we rode into New Glarus, WI, the home of the New Glarus Brewery. Their beer is exceptional, but they’ve decided to only sell it in Wisconsin, which means, if you're there, stock up. We grabbed burgers, beer, and cheese curds at Toffler’s and then rode back to the barn. We had a few beers and Dog Walkers, ate a bunch of snacks, and crashed.

The next day, we spent about two hours wandering and found that there aren’t any bad roads in this area. I wish I could give you details about where we rode, but I can’t. We started by following the rides in the maps I downloaded, but soon decided to take some random detour and kept exploring. Speed limits are around 60-70 MPH, and all roads were designed so that trucks can easily maneuver on them. This means that broad turns can be taken at fast speeds while staying safe and maintaining good sight lines.

The remainder of the time was filled discussing the company's plans, outlining new processes, and articulating our culture. 

For dinner the last night, we went to Pancho and Lefty’s Outlaw Grill where Nick scarfed down a double cheeseburger while the rest of us sat in awe of his 25-year-old metabolism.

The next day, we rode back to Woodstock Harley to return the bikes, and grabbed one final team dinner at Porky's for our last team meal—BBQ.

I found the trip to be perfect. It had a nice balance of team-building and camaraderie, riding and work. And it forced Chris to finally get his endorsement (oh, and a correctly-gendered license). All in all, I'd call it a success.

Editor's Note: Soon after we published this feature, we heard from rider Carl from Minnesota who shared some great intel about the Driftless Area and a charity ride that we are happy to share here.