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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

  • Boulder, Colorado

    Sunshine Lion's Lair Loop

    5.0
    5.05 mi / 1257 ft gain
    This 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...
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  • Boulder, Colorado

    Mount Sanitas Loop & Settlers Park

    4.4
    3.83 mi / 1371 ft gain
    First 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...
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  • Silverthorne, Colorado

    Lily Pad Lake

    4.7
    3.27 mi / 531 ft gain
    Lily 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...
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  • Boulder, Colorado

    Royal Arch Trail

    4.4
    3.32 mi / 1220 ft gain
    Royal 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 ...
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  • Boulder, Colorado

    Hike to the 1st Flatiron

    4.6
    2.4 mi / 1422 ft gain
    Starting 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...
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  • Boulder, Colorado

    Green Mountain via Chautauqua Park

    4.5
    5.24 mi / 2467 ft gain
    Starting 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 ...
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  • Boulder, Colorado

    Hike the Chautauqua Trail to the Ski Jump Trail

    5.0
    1.55 mi
    Beginning 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...
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  • Boulder, Colorado

    Woods Quarry via NCAR

    4.2
    3.28 mi / 755 ft gain
    You 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...
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  • Boulder, Colorado

    Hike the Enchanted Mesa Trail

    4.0
    1.4 mi / 440 ft gain
    Start 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...
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  • Evergreen, Colorado

    Hike the South Loop at Elk Meadow Park

    3.0
    4.4 mi
    Elk 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...
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  • Boulder, Colorado

    Mars Blocks via Bear Canyon Trailhead

    4.89 mi / 1923 ft gain
    The 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...
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  • Boulder, Colorado

    Hike South Boulder Peak

    4.5
    6.7 mi / 2900 ft gain
    Starting 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...
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  • Boulder, Colorado

    Hike the Big Bluestem Trail Loop

    4.0
    4.35 mi / 841 ft gain
    This 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...
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  • Boulder, Colorado

    Hike Bear Peak

    4.8
    7 mi / 2810 ft gain
    The 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...
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  • Boulder, Colorado

    Doudy Draw Trail

    4.37 mi / 433 ft gain
    Doudy Draw Trail is an out-and-back trail where you may see beautiful wildflowers located near Boulder, Colorado.
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  • Boulder, Colorado

    Scramble Angel's Way

    5 mi / 1000 ft gain
    Angel'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...
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