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The Best Backpacking in Winslow

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

Top backpacking spots in and near Winslow

  • Bowdoinham, Maine

    Swan Island Loop

    7.48 mi / 492 ft gain
    Swan Island Loop is a loop trail that takes you by a river located near Bowdoinham, Maine.
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  • Weld, Maine

    Hike Tumbledown Mountain

    5.6 mi / 2300 ft gain
    To keep the hike as short as possible, the hike can be an out and back at 5.6 miles, but if you wanted to make it a loop that is possible and adds only an additional 2 miles or so. We took the Brook Trail up to the summit (which passes by the alpine lake) and then followed it back down. To hike t...
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  • New Portland, Maine

    Bigelow Loop

    12.28 mi / 2507 ft gain
    Bigelow Loop is a loop trail that takes you by the lake located near New Portland, Maine.
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  • Carrabassett Valley, Maine

    Crocker Mountain and South Crocker Mountain via Appalachian Trail

    6.58 mi / 2867 ft gain
    Crocker Mountain and South Crocker Mountain via Appalachian Trail is an out-and-back trail where you may see beautiful wildflowers located near Kingfield, Maine.
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