Highland Is Home Episode 5: Generations

Over the last fifteen years, the Highland Family has grown in ways we could have never imagined. In this year’s final episode of Highland Is Home, we talk to four of the families who have found a second home at Highland, where they can share their passion for bikes and bring up a new generation of riders: meet the Bensons, the Andersons, the Morrises, and the Paysons.

Corey and Sherri Benson both grew up close to the mountain, spending winters at The Highlands when it was still a local ski hill. It wasn’t until their three sons took up mountain biking that they started looking into the sport themselves. “They went to camp,” Sherri explains. “And we were like, ‘why are they having all the fun?'” Now, all five Bensons are avid riders and familiar faces to anyone who frequents the lift line. 

On days that Corey and Sherri can’t make it to the mountain themselves, they feel comfortable leaving the boys in the capable hands of their Highland Family. Some parents may balk at the idea of dropping their young kids off at the chairlift with a mountain bike, a full-face helmet, and a smile and wave, but these days the Bensons don’t bat an eye. They know that any day of the week, their kids will have a network of fellow riders (friends, peers, parents, staff, and anyone in between) looking out for them and keeping the stoke high. 


Jack Benson touches the sky

If there were an encyclopedia entry for ‘Highland Family,’ it wouldn’t be complete without a photo of Caitlyn and Billy Anderson. They both worked at Highland in the early years of the park (in the café and bike shop, respectively) before getting married and welcoming their two sons, Charlie and Gunner: part of the first generation of little shredders to be born into the Highland Family. The boys have never known a life without Highland dirt on their tires.


Billy and Charlie try some new tricks on the strider bike at the 2016 Brodown Showdown

Caitlyn and Billy have seen every evolution of Highland firsthand: years when fifty riders showing up on Saturday constituted a busy weekend, seasons characterized by wild parties, and now the family-oriented mountain where they’ve introduced their children to their shared love of riding. For them, the Highland experience has come full circle. “We just love this place so much, and to able to share it with our kids…well, that’s what you look for when you have kids, right?” Caitlyn says. “This is our passion.”


Caitlyn and Billy charge down Lower Happy Hour

Kristi and Jack Morris found Highland through the lessons program. They convinced Kristi’s dad to give it a shot, and now that they’ve also gotten their son and nephew involved mountain biking is a passion the family shares across three generations. “The smiles on their faces…it’s just outstanding,” Jack says. The kids love the pump track in particular, but all five of them have been steadily working on progressing their way through more difficult terrain, conquering new trails and jumps at a fun and supportive pace. In what has been an exceptionally challenging year for pretty much everyone, the adults love hearing the kids so excited and happy about something. “Being able to come here and be outside and have a good time on a bike…it sort of makes it all worthwhile.”


Grady floats above it all

The Paysons have been riding at Highland for years. Justin learned about the park from a friend in the early seasons, and as his kids got older he couldn’t wait to introduce the whole family to the sport. Erika herself had only just started riding in her thirties, but once she visited Highland for the first time she didn’t want to go anywhere else. “That meant that I got to ride a lot more,” Justin says with a smile.

“Their confidence level is boosted so much,” Erika says of the kids. “It’s been amazing.” Justin and Erika recall their first time visiting the park with both Grady and Kyla. They ended up walking their bikes down almost every trail they attempted. Now, Grady is hitting almost every major feature on the mountain. Kyla has conquered all of the green trails and is working on picking off all of the blues. Between the camp programs that both kids have attended over the years and the unwavering support of the Highland Family, their riding has continued to progress. There’s no telling where it will take them next.