How to Explore Vail Like a Local

If you haven’t visited yet, chances are Vail—Colorado’s quintessential mountain town—is high on your bucket list. Its walkable villages, cobblestone streets, and old-world Tyrolean alpine architecture add to its sweeping Rocky Mountain views.

But what keeps mountain-loving visitors coming back again and again? Unbeatable access to world-class hiking, biking, and a wide range of family-friendly outdoor adventures—all just steps from Vail Village and Lionshead.

To truly understand what makes Vail so special, you need insight from someone who lives it every day. That’s why we turned to Josiah Middaugh, a longtime local and elite athlete. A 15-time XTERRA USA national champion, 2015 XTERRA world champion, five-time Fat Bike World Champion, six-time USSSA National Snowshoe champion, and Eco-Challenge Fiji competitor, Middaugh has explored his home as both an adventure-seeking athlete and a parent of three.

“My family and I moved to Vail in June of 2000, and we were immediately in awe of the Gore Range and the vibrant, active community,” Middaugh recalls. “We quickly fell in love with the summers—spending our weekends exploring the endless trails that wind through Vail and East Vail.” It’s a sentiment he’s carried ever since. As Middaugh puts it, “You come for the winter, but you stay for the summer.”

We asked Middaugh to share a few of his favorite spots and tips for making the most of your time in Vail—whether you’re training like a pro or adventuring with the family.

Outside: What are your favorite trails to run or hike when you’re training? 

Josiah Middaugh: I am a big fan of the North Trails, including Trapper’s Run, Buffehr Creek to Red Sandstone, and Red Sandstone to Son of Middle Creek, and the Son of Middle Creek Trail, which is also a popular singletrack for mountain bikers. They are easily accessible from Vail, so it can be a short ride, or you can link some of the trails together and it can be a long adventure.

Where are the best places to ride? 

On the road bike, Vail Pass is a great go-to ride. Once you pass the gate, the road is free of cars for a nine-mile climb up to 10,600 feet. If you don’t want all that climbing, one option is to shuttle to the top and ride down. Renting a bike in Vail is easy, too—just head to one of the many bike rental shops in the villages to get geared up.

After a solid training session, where do you like to refuel? 

Sometimes during or after a long ride, I will stop into the Hythe to visit Mountain Ration for a mocha and some grab-and-go food. My favorite burrito is the veggie breakfast burrito from Loaded Joe’s.

What are some of your go-to places for a family adventure? 

When we have visitors in town, we often take a ride up the Eagle Bahn Gondola (#19) in Lionshead Village for a short hike. A great activity with the kids is the alpine coaster. We also have some fond memories of our kids playing at the Pirate Ship Park when they were little—but now they’re onto bigger adventures like XTERRA USA and world championships and world cups.

Discover Vail is the official destination-marketing organization for Vail, Colorado. It’s responsible for promoting Vail as a premier year-round destination, focusing on boosting tourism, and enhancing the economic health of Vail.