City Sights by Segway

It was a perfect July day and our wheels rolled along the riverside path, passing sightseers, dog walkers and lunchtime joggers. Our tour guide, well-known Bend resident John Flannery, rolled ahead of me and gave the signal to “hold up,” so I gently leaned back and came to a halt. The hum of our Segways quieted, and we gathered around to learn about Bend’s rich history.

This was my first experience driving a Segway, and I was already charmed. I was on the Bend City Sights Segway Tour with The Bend Tour Company, owned by Flannery and Bret Graham. Segways are two-wheeled, self-balancing, battery-powered electric vehicles, invented as an alternative means of transport. The driver stands upright and makes subtle movements to operate the Segway, which is why Flannery likes to call them “magic carpets.”

When I arrived at the tour company headquarters in the upper Old Mill District, I looked to Flannery with some trepidation. “It’s like riding a bike, right?” He smiled and laughed, “No, Miss Katy, not like a bike, but just as fun!” He then patiently coached us through getting on and off, moving forward, stopping and turning the Segway as we practiced navigating around traffic cones in the loading bay.

After getting comfortable on our new rides, our little group, including Flannery and Graham, set out on our tour towards the Deschutes River in the Old Mill District. I was reminded of how Bend was born as a rough-and-tumble logging town, built by harvesting lumber out of the nearby forests. I’ve lived in the heart of Bend for nearly 20 years and I still learned fascinating new tidbits about this place I call home from Flannery, like my new favorite term “Pond Monkeys”—the millworkers that scrambled across the logs in the river, guiding the lumber downstream to the mill.

From the Old Mill, we cruised through Farewell Bend Park and the Les Schwab Amphitheater as Flannery talked about the rise of public art in Bend and the foresight of the community in developing parks and public spaces. Rolling along the paved paths, kids pointed at us and looked to their parents for an explanation of what these funny two-wheeled machines were that they were seeing. Right around this time, I realized that I wasn’t even thinking about how to drive the Segway anymore, I was just doing it, easily making the gentle movements to turn, stop and roll. I was surprised at how quickly it became second nature, seemingly for any age or ability. Graham shared that the oldest Segway tour customer they’ve ever had was 88 years old.

From the amphitheater, we crossed the bridge overlooking the Bend Whitewater Park to Whiskey Flats, the neighborhood just north of Miller’s Landing Park. We were in my own neighborhood now, and I learned a lot of new history about the area I call home. In the 1920s, Whiskey Flats was the place to be if you were into making booze during Prohibition. Due to the neighborhood’s location on the banks of the Deschutes, the moonshiners could quickly dump their goods in the river when the authorities came around.

After cruising through Drake Park, we continued on our route to downtown Bend. This was the true test. Could we navigate through the Brooks Street breezeway, down Minnesota Street and across Wall and Bond Streets? It was no problem! I felt like a pro, zipping along and making confident turns as Flannery pointed out more public art and historic buildings along the way.

Ending our excursion back at the tour headquarters, we stepped off our motorized steeds and thanked Flannery for his wit, wisdom and superb Segway skills. It doesn’t matter if you are a longtime Bend resident or a new visitor, the Bend City Sights Segway Tour is an excellent way to explore Bend and learn about its history and culture. And c’mon, admit it, you know you’ve always wanted to try a Segway!



Segway Tours

The Bend Tour Company offers three different Segway Tours for ages 14 and older, as well as custom tours for groups.

Bend City Sights Segway Tour. A 1.5-hour tour including the Old Mill District, Deschutes River, Whiskey Flats, Drake Park and downtown Bend.

Bend Sunset Spectacular Segway Tour. A 2.5-hour tour that includes the Bend City Sights route, with additional stops to sample food and drinks along the way.

Old Mill Centennial Segway Tour. A special 1.5-hour tour celebrating Bend’s industrial history, led by a Deschutes Historical Museum guide.

Learn more at

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