Middlebury, Vermont

Looking for the best hiking in Middlebury? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Middlebury. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Middlebury

  • Cambridge, Vermont

    Sterling Pond Trail

    5.0
    2.28 mi / 876 ft gain
    Sterling Pond trail begins across the street from a parking area on Route 108, about 3 miles south of Smugglers' Notch Resort. Keep in mind that the road is closed to vehicles once the snow falls, so if you want to hike this area in the winter, you'll have to park about 40 minutes away and hike ...
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  • Lake Placid, New York

    Cobble Hill

    5.0
    2.31 mi / 463 ft gain
    Looking for a great family hike up in the Adirondacks? Take a look into Cobble Hill right off of Mirror Lake in Lake Placid. This is a perfect hike for those with younger kids and want to expose them to hiking. Cobble Hill has a little bit of everything all packed into the short distance. The ...
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  • Wilmington, New York

    Hike Cobble Lookout in the Wilmington Wild Forest

    4.7
    2.6 mi / 240 ft gain
    Park at the trailhead located on County Route 18A just after the split from Whiteface Veteran's Memorial Highway in Wilmington, NY. There is a small parking lot for 4-5 cars and a pull off just ahead for another 3-4 cars. The trail begins at the back of the parking area. Following the contour of ...
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  • North Creek, New York

    Gore Mountain via Schaefer Trail

    5.0
    9.14 mi / 2562 ft gain
    You will start this hike following the blue blazed Schaefer trail. Though the sign shows 5.8 miles to the summit it is actually only 5.0 miles. Much of the way you follow Roaring Brook which has many waterfalls along the way. Just after the North Creek Reservoir you will get your first glance at...
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  • Hartford, Vermont

    Camp at Quechee State Park

    4.0
    Located on the Ottauquechee River, Quechee State Park offers camping options right beside one of Vermont's most famous gorges—Quechee Gorge. The steel bridge that passes over the 165 ft. gorge is just one of many spectacular views in this area. Quechee State Park is on Route 4 and easily accessi...
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  • Lake Placid, New York

    McKenzie and Haystack Mountains

    12.24 mi / 3553 ft gain
    McKenzie Mountain stands at 3,861 feet and is one of the highest 100 in the Adirondacks. Haystack Mountain stands at 2,874 feet. Both are part of the Saranac 6ers Challenge. The trailhead for this route to McKenzie and Haystack is located on route 86 in Ray Brook, there is a nice parking area of...
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  • Wolcott, Vermont

    Elmore Mountain Fire Tower Loop

    4.0
    5.43 mi / 1535 ft gain
    If hiking in off season when the park is closed, begin from the lower parking lot or the "day use area". If hiking while the park is open you can drive to the upper parking lot (subtract about 1.4 miles from total distance) Beginning from the lower parking lot make you way through the gate and i...
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  • Groton, Vermont

    Hike to Owl's Head Trail Overlook

    4.0
    3 mi / 200 ft gain
    Starting at 1746 ft of elevation, this easy 3 mile hike (RT) pays off with a dramatic view of Lake Groton, Kettle Pond and the Green Mountains of Vermont. The trail head begins in New Discovery Park, along the dirt road to Osmore Pond. There is room to pull off the dirt road and park near the t...
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