Best Challenging Day Hikes Near Winter Park, Colorado

Disclaimer: You should only be hiking trails that aren’t overcrowded during the height of the COVID-19 pandemic, and keep at least a six-foot distance from others. Before taking on any outdoor activity, be sure to follow all CDC guidelines, state-by-state regulations, and to stay up-to-date on changing circumstances.

Do you enjoy spending a grueling afternoon up above treeline? Do you thrive on Type II fun? If so, these day hikes in Grand County, Colorado, are right up your alley.

These trails are steep, have rough terrain, moderate exposure, and a considerable amount of elevation gain. They are all out-and-back routes, and I would only recommend them to experienced hikers who are comfortable at high elevation. As a general rule of thumb, in the summer months, I usually like to start hiking by 5:30 a.m. Bring a few liters of water for each person to drink. I would recommend wearing sturdy hiking shoes, and having sunscreen. Although I prefer to hike without, trekking poles would be useful if you have one. Be sure to bring a jacket because it can get windy above treeline.

1) Devil’s Thumb Trail
Distance: 7 miles to Devil’s Thumb Pass; 8 miles to The Devil’s Thumb
Difficulty: Hard
Parking: Here

The Devil’s Thumb Trail is located in Fraser. The terrain is steep and gains around 2,250 feet from the parking lot to the top of Devil’s Thumb Pass. There are a lot of boulders, and sometimes an occasional downed tree.

This beautiful route passes through a dense alpine forest, a meadow where you can spot moose relaxing, and has an uphill slog through the alpine tundra. Please be aware of your surroundings and be sure to watch out for the moose—there are a lot of them, and although they are cute, they are large and can be territorial.

This is a wonderful day hike that goes by pretty quickly. It usually takes my husband and me around four hours total to complete this trail. I wish I had recorded the actual distance to the Devil’s Thumb formation and back. This is the point that we usually hike to, and I believe that it makes the total distance around 8.4 miles. Hiking to the rock formation is only a bit farther than this route to the top off the pass listed on AllTrails.

The Devil’s Thumb is a very obvious point of interest, and you won’t get lost if you decide to venture all the way to the rock formation. The trail that goes back to the car is the only trail that brings you down the mountain, and there are wooden blazes marking the way.

If you have a solid grip of the area, you can hike all day on the Divide by The Devil’s Thumb. I have done a lot of off-trail exploring in these parts. There are plenty of peaks to be bagged, and you can even find some spicy class four scrambles. Stick to the main trail if you do not have the proper equipment or adequate experience to venture forward.

2) Mount Flora Trail (option to continue to Parry’s Peak)
Distance: 6 miles to Mount Flora; 14 miles to Parry’s Peak
Difficulty: Hard
Parking: Here

The trail to Mount Flora begins at the top of Berthoud Pass. You can hike to the weather station on the top of Colorado Mines Peak and then over to Mount Flora, but I prefer to avoid the crowd and take the standard trail. These peaks are best hiked from late May through the end of September. This hike is almost entirely above treeline, and the terrain is steep, but rather smooth. It does get a little rocky if you choose to adventure across the ridgeline and over to Parry’s Peak.

This area can be crowded during all times of the year. Hiking is very popular during the summer and early fall months. Backcountry skiing is huge in the winter. During the non-snowy season, most people who are up on Berthoud Pass are usually either there to take pictures or are just hiking on the road that goes up to the weather station. It is an incredibly scenic area, and it is definitely worth visiting.

Make sure to check the forecast. Only hike this trail in good weather, and keep an eye out for clouds or storms rolling in. It is fairly easy to bail back to your car if you are only going to Mount Flora, but remember that it’s three miles down from the summit. Lightning is deadly, and the rare occasion of a summertime thunder-snow attack is not as fun as it sounds. I don’t think thunder-snow is a scientific term, but I promise that you do not want to be caught in a situation where it is simultaneously thundering and snowing above treeline.

The path to Parry’s Peak is extremely obvious, and many CDT thru-hikers choose this route as part of their journey. Follow the direct ridgeline from Mount Flora, over to Mount Eva, and then across to Parry’s Peak. Be prepared to consistently gain and lose elevation over the course of the trail from Mount Flora and beyond. Parry’s Peak sits at 13,392 feet, and is the highest summit within this small section of the Divide. This hike is pretty awesome because you can tag four high summits on the Continental Divide in a 14-mile day.

3) Byers Peak Trail
Distance: 9.1 miles
Difficulty: Hard
Parking: Here

Byers Peak sits at 12,804 feet. It is iconic because it towers over the valley, and it seems rather lonely over there in the Fraser Experimental Forest. The summit has a flat and sort of square-shaped top. Byers Peak looks very different, but somehow the exact same no matter where you look at it from within the area.

This trail gains 2,988 feet from the parking area to the summit. The first two miles are rather mellow. The trail starts on an old forest service road that is now closed to vehicles, and you can bike up the road to the official trailhead.

The remainder of the trail is steep, rocky, and requires some light scrambling to reach the top. For reference, we did this hike with two dogs, so the scrambling isn’t too serious, but it can be nerve-racking.  The trail gets steep above treeline as it follows the long ridge to the summit. It’s usually windy up there, as Byers Peak sits on its own in the middle of a large valley. This hike offers incredible views, and the trail usually isn’t super crowded.

This hike took my husband and me around four hours total. In a nutshell, the trail to Byers Peak includes four miles on a washboard road, a lot of switchbacks along through the trees, and rather steep terrain above along the ridgeline.

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Comments 1

  • Allie : Apr 22nd

    Great pics and info! Thanks for the Alltrails links, I was able to click and put these directly into my save list. 🙂



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