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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

    Hike the Tenderfoot Trail

    4.3
    2.1 mi / 400 ft gain
    From Chautauqua Park in Boulder, follow Baseline Road west (if you are driving up the mountain, you are golden). Drive 3.4 miles up Flagstaff Road and look for the sign for Realization Point on your right. It’s a little tricky to see from the road, so keep an eye on your odometer. The trail star...
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  • Boulder, Colorado

    Rattlesnake Gulch Trail

    3.49 mi / 1093 ft gain
    Rattlesnake Gulch Trail is a loop trail that takes you by a river located near Eldorado Springs, Colorado.
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  • Boulder, Colorado

    Hike the Rattlesnake Gulch Trail

    4.3
    5.3 mi / 1304 ft gain
    Rattlesnake Gulch Trail is located in Eldorado Canyon State Park. It is a short 20 minute drive from Boulder and is one of three hikes in the park. You will need to pay an entrance fee to get inside to the park which costs $8. The trail is approximately 2.8 miles one way and carries a consistent ...
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  • Grand Lake, Colorado

    Hike to Cascade Falls, Rocky Mountain NP

    5.0
    6.8 mi / 425 ft gain
    Cascade Falls is accessed through the North Inlet Trail on the western side of Rocky Mountain National Park. The trailhead, North Inlet Trailhead, is north of the main town area of Grand Lake. Parking at the trailhead is limited, so hikers can also park along the road leading to the trailhead. Th...
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  • Grand Lake, Colorado

    Backpack the CDT Loop in Rocky Mountain NP

    24.3 mi / 4000 ft gain
    This section of the CDT begins at the North Inlet trailhead, located on the western side of Rocky Mountain National Park. The trailhead is north of the main town area of Grand Lake. Parking at the trailhead is limited, so hikers can also park along the road leading to the trailhead. The hike foll...
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  • Allenspark, Colorado

    Sandbeach Lake Trail

    4.0
    8.56 mi / 2057 ft gain
    Sandbeach Lake is best known for (as you can probably guess) its wide sandy shore. At nearly 50 feet deep, it is one of Rocky Mountain National Parks deepest lakes. If you are looking to fish at the lake, make sure to bring barbless flies and lures. There are six official campsites (1.8 miles Hol...
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  • Boulder, Colorado

    Hike the Eldorado Canyon Trail

    4.5
    6.3 mi / 1875 ft gain
    Eldorado Canyon Trail makes for a great day hike, with great views and a steady, challenging uphill – bring lots of water!For something shorter, try Streamside Trail (1 mile roundtrip), Fowler Trail (1.4 miles), or Rattlesnake Gulch (2.8 miles). Streamside, appropriately, leads you alongside a cr...
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  • Swan Mountain Road, Colorado

    Sapphire Point Overlook

    3.3
    0.62 mi / 49 ft gain
    This short, 0.6 mile loop hike gives a beautiful view of Lake Dillon and is an easy, family-friendly hike. Dogs are allowed but must be kept on leash. The trail is clear cut and descends a few feet while looping around the side of the mountain to the overlook point.  It is definitely a worthwhil...
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  • Silverthorne, Colorado

    Hike to Old Dillon Reservoir

    4.5
    1.7 mi / 137 ft gain
    Today, Lake Dillon is one of the biggest attractions in the Dillon Valley, attracting boaters, anglers, and campers. However, the large reservoir we know today was not the first one in the area.  The Old Dillon Reservoir was built in the 1930s to supply water to the original town of Dillon, which...
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  • Golden, Colorado

    Hike the Sawmill to Maverick Loop

    4.3
    2 mi / 450 ft gain
    For this adventure, you'll be completing the Sawmill to Maverick loop. It is a short, but gentle trail that will take you through open meadows, to pine forests, and great views of Denver and Golden.Starting from the west parking area, cross the road and hit the Sawmill Trail. This trail starts ou...
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  • Boulder, Colorado

    Green Mountain via Gregory Canyon and Ranger Trail

    5.45 mi / 2313 ft gain
    Green Mountain via Gregory Canyon and Ranger Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Boulder, Colorado.
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  • Boulder, Colorado

    Hike the Saddle Rock Trail

    5.0
    2.6 mi / 1500 ft gain
    You can either start the from the Gregory Canyon Trailhead or the main Chautauqua trail.  At the Chautauqua trailhead you will need to pay for parking on Saturdays and Sundays and at the Gregory Canyon Trailhead you will need to pay for parking if your car is not registered in Boulder. If you sta...
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  • Boulder, Colorado

    Hike the Red Rocks Loop Trail

    3.7
    1 mi
    Parking is available on either Canyon or Sunshine Roads. During the weekends it tends to get crowded around sunset so plan accordingly. The entire trail is a loop and is a little over 1 mile in length so it doesn't take too long. The main feature is the massive red sand stone rocks that jut out o...
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  • Boulder, Colorado

    Mount Sanitas Peak Trail

    2.57 mi / 1296 ft gain
    Explore the natural wonders of Boulder, Colorado, with the Mount Sanitas Peak Trail hike. This trail offers stunning vistas of the Rocky Mountain wilderness and Colorado's Front Range. This hike is just over 2.5 miles with about 1300 feet of elevation gain.  Parking and Access: Start your hik...
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  • Boulder, Colorado

    Red Rocks and Anemone Trail Loop

    1.26 mi / 459 ft gain
    Red Rocks and Anemone Trail Loop is a loop trail that provides a good opportunity to view wildlife located near Boulder, Colorado.
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  • Boulder, Colorado

    Mount Sanitas + Sunshine Canyon loop

    5.03 mi / 1257 ft gain
    This loop takes you up Sunshine Canyon, a milder and less crowded grade when compared to the popular Sanitas ridge. You'll head up the canyon for a bit before reaching the terminus of the canyon trail -- where you'll cross the road to pick up on the Lions Lair connector. Continue following this u...
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