Winter Park, Colorado
Looking for the best hiking in Winter Park? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Winter Park. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Winter Park
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Boulder, Colorado
Sunshine Lion's Lair Loop
5.05.05 mi / 1257 ft gainThis is a mix of trails that will bring you on an easy loop to the peak of Mt Sanitas, but will keep you away from the usual crowds of the more well-known paths up. The hike is a clear path that brings you 5+ miles from around 5,500 ft in elevation to 6,800. You'll start at the Centennial Trail...Read more -
Boulder, Colorado
Mount Sanitas Loop & Settlers Park
4.43.83 mi / 1371 ft gainFirst off, these are two different hikes but both stem from the same parking lot and Settlers Park is a mere 5 minutes away from where you park so why not kill two birds with one stone? One of the more popular hikes in Boulder, Mount Sanitas is a 3 mile hike that quickly scales nearly 1,350 feet...Read more -
Silverthorne, Colorado
Lily Pad Lake
4.73.27 mi / 531 ft gainLily Pad Lake is a well known destination just outside of Silverthorne and in the Eagle's Nest Wilderness. The trail may be heavily trafficked on the weekends, but solitude can still be found in the early mornings or during the weekdays. The trail starts at the Lily Pad Lake Trailhead, just to t...Read more -
Boulder, Colorado
Royal Arch Trail
4.43.32 mi / 1220 ft gainRoyal Arch Trail climbs up Boulder's famous Chautauqua Park to an archway formed by sandstone rocks that tower over thirty feet high. Start at the Chautauqua Trail Station by the Ranger Station, and continue up Bluebell Road for 0.7 miles. You will then arrive at a more forested area, where you ...Read more -
Boulder, Colorado
Hike to the 1st Flatiron
4.62.4 mi / 1422 ft gainStarting at the ever-popular and ever-populated Chautauqua Trailhead, take the main trail (a highway version of a dirt trail) straight towards the Flatirons. Continue going straight passed the Ski Jump trail to your right (0.2 mi.), then at a crossroads with the Bluebell-Baird trail (0.3 mi.) tur...Read more -
Boulder, Colorado
Green Mountain via Chautauqua Park
4.55.24 mi / 2467 ft gainStarting from the popular Chautauqua Park trailhead, head west on the main trail to the first branch off onto a smaller trail that will take you toward Baseline Road. Follow this trail until it eventually connects with Gregory Canyon Trailhead—you can park at this trailhead if you wish, but miss ...Read more -
Boulder, Colorado
Hike the Chautauqua Trail to the Ski Jump Trail
5.01.55 miBeginning at the Chautauqua Trailhead, the Chautauqua Trail goes for 0.6 miles before connecting with the Bluebell-Baird Trail. From here it becomes a choose-your-own-adventure hike. For a short, simple hike you can do with people who aren't ready for lots of elevation gain, take a right and conn...Read more -
Boulder, Colorado
Woods Quarry via NCAR
4.23.28 mi / 755 ft gainYou can start from Chautauqua Park, but I prefer to start at NCAR, especially since there is ample parking and you can take a bathroom break inside before hitting the trail. From the intersection of Table Mesa Drive and Broadway in Boulder, drive west on Table Mesa to its end at the NCAR buildin...Read more -
Boulder, Colorado
Hike the Enchanted Mesa Trail
4.01.4 mi / 440 ft gainStart out on McClintock Trail for 0.7 miles (this particular stretch can get muddy), before switching over to Enchanted Mesa Trail. To add a scenic 0.4 miles to your hike, take the Quarry Loop by turning right at the stone cabin, then following the steps up to the quarry, where you can overlook t...Read more -
Evergreen, Colorado
Hike the South Loop at Elk Meadow Park
3.04.4 miElk Meadow Park near Evergreen, CO spans 1,140 acres of open meadow and pine forests and has over 16 miles of managed trails by Jeffco Open Space. This park will give the visitor a diverse taste of ecosystems and terrain and is perfect for trail runners, families, or those seeking a quick excursi...Read more -
Boulder, Colorado
Mars Blocks via Bear Canyon Trailhead
4.89 mi / 1923 ft gainThe Bear Canyon Trailhead is just one of many starting points for this hike, one could also start at NCAR, North Fork Shanahan, or any point on the Mesa Trail. For the purposes of this adventure, I'll start at Bear Canyon Trailhead in South Boulder. This hike will take you about 2-4 hours dependi...Read more -
Boulder, Colorado
Hike South Boulder Peak
4.56.7 mi / 2900 ft gainStarting at the Mesa trailhead, continue a half a mile through a relatively even grade before arriving at the North Fork Shanahan trailhead, which will take you another half a mile on much steeper grade up to Fern Canyon where you will start a much harder portion of the hike; here, you'll head st...Read more -
Boulder, Colorado
Hike the Big Bluestem Trail Loop
4.04.35 mi / 841 ft gainThis is a great spot for an easy/moderate hike or trail run. The trail is accessible year round and can often be hiked in winter as well as other seasons. You start out at the Mesa Trailhead parking lot off of Hwy 170. There is a parking lot here but this is a starting spot for several hikes into...Read more -
Boulder, Colorado
Hike Bear Peak
4.87 mi / 2810 ft gainThe best advice I can give you? Wake up early to start this hike.Even though the Bear Peak hike will only take you about 4-5 hours round trip, it will still be advantageous to get off the mountain before afternoon and evening storms might pass through. This is a steep 7-mile out and back trail.St...Read more -
Boulder, Colorado
Doudy Draw Trail
4.37 mi / 433 ft gainDoudy Draw Trail is an out-and-back trail where you may see beautiful wildflowers located near Boulder, Colorado.Read more -
Boulder, Colorado
Scramble Angel's Way
5 mi / 1000 ft gainAngel's Way is an amazing 8 pitch rock climb scramble (5.2) that is tucked away in Skunk Canyon, hidden from the crowds of Chautauqua. The best part of this scramble is you only need your climbing shoes and chalk-bag. It is similar to the 'Free Way' on the Second Flatiron. I would encourage ev...Read more