Climb out of the Hilltop Ski Area parking lot on a September morning and the singletrack does the talking. Drone Lane switchbacks up through spruce and cottonwood, feeds into Queen Bee Loop, and from there splits toward Janice's Jive or the long grassy drop of The Hive. None of it looks manufactured. There's no visitor center, no interpretive signage explaining what you're riding through. It just works, the way a well-worn path through someone's backyard works, because in a real sense it is one.
That backyard just got a national label. On March 31, 2026, the International Mountain Bicycling Association named Anchorage a Trail Town, one of only 28 communities in the country to hold the designation. The announcement cited more than 50 miles of mountain bike specific singletrack across the city, much of it built at Kincaid Park and on the Hillside. Will Taygan, executive director of the local nonprofit Chugach Mountain Bike Riders, called the recognition a chance to tell visitors there's reason to stay another day in Anchorage. Five mountain biking nonprofits operate in this city alone, which tells you something about how much of this trail network exists because people decided to build it themselves rather than wait for a budget line.
The math nobody did
Here's the part that doesn't show up in the press release. The organization responsible for almost all of that singletrack, Singletrack Advocates, has been building trail in Anchorage since 2004. Add up every mile they've cut since then and you land close to 40. Break that total out by year and location, and the Hillside carries nearly half of it.
| Year | Location | New singletrack |
|---|---|---|
| 2008 | Hillside | 8 miles |
| 2011 | Kincaid Park | 9 miles |
| 2014 | Kincaid Park | 7 miles |
| 2018 | Hillside | 5 miles |
| 2022 | Chugach State Park | 6 miles |
| 2025 | Hillside (Service Singletrack) | 6 miles |
Nineteen of those roughly 40 miles sit on the Hillside. That's not a rounding error. It means the trail system that just earned Anchorage a spot alongside 27 other Trail Towns nationwide is, by mileage, closer to a Hillside project with a citywide footprint than a citywide project that happens to touch the Hillside. If you live up here and use these trails on a normal week, you're not adjacent to the story. You're most of it.
Nobody waited on a budget
The reason the timeline reads the way it does, in bursts eight years apart rather than one continuous build-out, is that every mile came from grants and fundraising rather than a municipal capital plan. Singletrack Advocates is entirely volunteer-run. The first 8-mile Hillside network in 2008 was hand-built. Phase Two, another 5 miles, wasn't finished until a decade later, in the fall of 2018.
The most recent addition, a 6-mile beginner and intermediate loop connecting Service High School to Hilltop known as the Service Singletrack Project, took its own path to completion. Its first 2.5 miles opened while the group was still raising money for the rest. The full loop was finished in 2025, funded by $600,000 raised across all phases of the project. When the newest segment opened, it didn't happen quietly. Mountain bikers from around Anchorage showed up on October 1, 2025 for a ribbon cutting, snacks, and a chance to ride the new sections before the season closed out.
That's the pattern behind every mile on this map. Somebody pitched a route to the Hillside Community Council, somebody else ran a fundraiser, and eventually a crew of volunteers with hand tools turned a proposal into a trail with a name and a difficulty rating.
What changed since you last rode
If your last lap through Hillside Park was earlier this summer, a few things are different now, and a few are still ahead before the trails go quiet for the season.
- The Alaska MTB Marathon returned for its second year on July 18, 2026, running a 15-mile loop through Hillside terrain that includes Jeff's Whoop Whoop and the technical, root-heavy Brown and Black Bear trails. A share of every entry fee went back to Singletrack Advocates.
- The MTB4W Festival, built around a no-drop social ride and skill clinics, staged out of the Hilltop Chalet this year with support from the Trek Store of Anchorage and The Dirt House, plus lunch from Finn's Kitchen and Wild Scoops.
- The Alaska Mountain Bike Festival brought back the Kendall Toyota of Anchorage Downhill Race Series along with a new e-bike race, both centered at Hilltop.
None of these events existed on the Hillside a decade ago. Now they're a normal part of the summer calendar, using trail names, like Ticket to Ride at 1.6 miles, that most Anchorage residents outside the neighborhood have never heard of.
Not just a bike network
The Trail Town designation is a mountain biking story, but the trail system underneath it serves more than one kind of resident. In May 2026, Audubon Alaska launched a new Anchorage Birding Trail covering 35 locations from Eagle River to Whittier, and Hillside Park made the list as one of what the group's communications manager Lauren Cusimano called a lesser known site worth a look. The organization updated its checklist of Anchorage area birds for the first time since 2014, and nearly 300 species have now been recorded within city limits.
The Besh Lighted Loop, a 3.2-mile trail that parallels Abbott Road, shows up on trip logs for cross-country skiing and hiking as often as it does for birding, with breaks in the tree line opening onto the Chugach Mountains. It's the same physical network the bikers use, accessed from the same points, Abbott Road near Service High School, Elmore Road, or Campbell Airstrip Road, just moving at a different pace.
The part worth sitting with
A national trail designation usually reads like a marketing win, a line for a tourism brochure. What the mileage actually shows is that Anchorage's new title rests on two decades of volunteer labor concentrated in one place, and that place is the ground behind Hillside driveways. The city didn't earn this by building a flagship park. It earned it because a nonprofit kept coming back to the same hillside, year after year, with hand tools and a fundraising page, until the network was big enough for the rest of the country to notice.
That's worth knowing if you already live here, because it means the thing you ride or walk or bird on most weeks isn't background scenery. It's the reason your neighborhood keeps showing up in stories that are ostensibly about the whole city.
If you're weighing a move to the Hillside, or thinking about what your own property near this trail system might be worth, the team at RE/MAX Dynamic Properties knows this neighborhood at the trail level, not just the listing level. Find the REALTOR® who's right for you.
