I have a confession to make: The first time I rode my bike up Lookout Mountain, I didn’t make it to the top.

It was August 2007. I’d recently moved to Denver, and as an avid cyclist, I’d read about the climb up Lookout, which I could access after riding about 15 miles from my home in northwest Denver. But there was a small problem. Or maybe a not-so-small problem. I’d moved to the Mile High City from sea level—and a pancake-flat landscape. Although I was fit, I was not acclimated to cycling at elevation (forget about climbing at elevation).

After riding for a little less than an hour, I reached the base of Lookout and started pedaling up the hill. It was a hot, late-summer morning, and the wind was gusting as I rounded some of the lower hairpin turns exposed to the valley. I immediately recognized why professional endurance athletes train at elevation and at the same time acknowledged that I was not, in fact, a professional endurance athlete. About a third of the way up, I took stock of the conditions and my fitness, tucked my tail between my legs, and turned around. It was not my proudest moment on two wheels.

Since that day 17 years ago, I’ve ridden Lookout Mountain—all the way to the top—countless times. I’ve become intimately acquainted with the different grades throughout the 4.5-mile ascent. I know the turns. I know the views. I know right where I’ll get a whiff of the scent of sunbaked pine needles (hint, it’s near the top). I know, based on the time it takes me to do the climb, if I’m fit or if I need to dial back the happy hour beers and spend more time on the bike.

Lookout is a relatively short climb, and it’s not all that steep, but from most locales in metro Denver you can get there from your front door. And it’s always a fun challenge that won’t wreck your day when you’re done (like, say, riding up Mt. Blue Sky). It is, without a doubt, my favorite ride in Colorado, and one of my favorites in the Lower 48.

But the Front Range, and Colorado as a whole, have innumerable scenic, demanding road rides. Here are five of my favorites—including Lookout—that you should have on your short list for this summer and fall. —Geoff Van Dyke

Confluence Park to Cherry Creek Reservoir

Looking west over I-225 on the Cherry Creek Trail. Photo by Geoff Van Dyke
  • Difficulty: Easy
  • Distance: 12.3 miles (one way)
  • Elevation gain: 610 feet

This easy out-and-back is popular for a bunch of reasons: It’s flat-ish, it provides access to a bunch of different parts of metro Denver, and the entirety of the ride is on a protected bike path so you don’t have to worry about people who are looking at their phones instead of actually driving their cars. It’s not the most beautiful ride in the state, but as you pedal through town, you’ll pass two golf courses, Four Mile Historic Park, and never are far from Cherry Creek.

As you leave Confluence Park, the ride southeast to the reservoir is ever-so-slightly uphill and you may experience a headwind. Take your time and save some energy for the short, steep hill you will ascend after you pass under I-225, which takes you into Cherry Creek State Park. Refill your water bottles near the beach at the reservoir, and delight in knowing your way back will be fast and furious as you pedal the slightly downhill path with the wind at your back.

Flagstaff Road (Super Flag)

  • Difficulty: Hard
  • Distance: 4.6 miles (one way)
  • Elevation gain: 2,163 feet
  • Average grade: 8.2 percent

This Boulder climb is renowned for its similarity to some of the famous—or infamous—Pyrenean climbs of the Tour de France, and indeed it was used as the final ascent during a stage in the 2012 U.S.A. Pro Challenge. You’ll see pros and semi-pros training here, and you see regular people grinding up the hill trying to set PRs on Strava.

The climb starts where Gregory Canyon Road runs into Flagstaff Road. From there, you will have a steady uphill grade—which averages 8.2 percent—for the rest of the climb. Pace yourself: There is a section known as “The Wall” during the last third of the climb (IYKYK). Once you reach the “second summit” of Flagstaff (the first summit is at the amphitheater, which is a 3.5-mile climb), turn around and enjoy the ride down the hill while planning where you’ll refuel in Boulder.

Lookout Mountain

The view from the top of Lookout Mountain. Photo by Geoff Van Dyke
  • Difficulty: Moderate
  • Distance: 4.5 miles (one way)
  • Elevation gain: 1,280 feet
  • Average grade: 5.4 percent

This one’s a challenging, but completely doable climb for accomplished cyclists and newbies alike. My favorite way to do Lookout is as the midway point in a roughly 35-mile ride from Highland Square in Denver. Ride west on 32nd Avenue through west Denver, Wheat Ridge, Applewood, right past the Coors Brewery, into Golden. Wind through town, skirt the edge of the Colorado School of Mines, and then start the climb toward the base of Lookout on 19th Street.

Once you pass through the Finlay McFarland pillars near Beverly Heights park, you will be on the climb proper, which is steady—even though the grade never reaches 10 percent—to the summit at the Buffalo Bill Museum and Grave. There, you can take in the view from the parking lot, refill your water bottles, and, if you brought your wallet, buy some snacks before the fun, nontechnical descent back into Golden.

Vail Pass (from East Vail)

  • Difficulty: Moderate
  • Distance: 4.5 miles (one way)
  • Elevation gain: 1,706 feet
  • Average grade: 4.2 percent

Like the ride to the Cherry Creek reservoir, this high elevation climb gets high marks because it’s on a recreational path. It’s not steep—although there are several very steep pitches—but keep in mind that you’ll be starting out in Vail at around 8,200 feet and topping out at roughly 10,500 feet at Vail Pass.

This ride is one segment of the popular Copper Triangle (Copper Mountain to Leadville to Minturn to Vail and back to Copper) and, in my opinion, is best enjoyed as part of a larger ride. If the Triangle loop is too much for you—it’s 79 miles with multiple mountain passes—you can try Vail to Copper and back again for a fun up-down-up-down ride. Or if you’ve got two cars and don’t mind doing a bit of extra driving, the ride from Leadville to Minturn and then up Vail Pass makes for a beautiful ride with stunning views of the Gore Range in every direction.

Maroon Bells

Road cyclists in front of the Maroon Bells
Maroon Bells. Getty Images
  • Difficulty: Moderate
  • Distance: 5 miles (one way)
  • Elevation gain: 1,234 feet
  • Average grade: 4.6 percent

This route rewards you with spectacular views of the West Elks with the iconic Pyramid Peak and Maroon Bells as the stars. Folks hike and walk their dogs here, and during the winter you’ll find cross-country skiers, snowmobilers, and occasionally fat-tire cyclists here, too.

Let’s be clear: You do not do this ride for the road itself, which is nearly straight and, honestly, pretty boring. What is not boring is the Maroon Creek Valley, through which you’re pedaling. You’ll see aspens galore, the backside of Highland Bowl, and the aforementioned fourteeners: Pyramid Peak, Maroon Peak, and North Maroon Peak. On top of that, the road is closed to private vehicles during the day from late May to late October to ease congestion at the Maroon Bells Scenic Area, so the only other traffic you’ll have to contend with are other cyclists, hikers, and the area’s wildlife.

Geoff Van Dyke
Geoff Van Dyke
Geoff Van Dyke is the editorial director of 5280 Publishing. Follow him on Twitter @GeoffVanDyke