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The Best Hiking in Portland

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

Top hiking spots in and near Portland

  • Middletown, Connecticut

    Hike Mattabesset River, Coginchaug River, And Cromwell Meadows

    11.4 mi / 75 ft gain
    Mattabesset River, Coginchaug River, and Cromwell Meadows is a 11.4 mile out and back hike where you may see beautiful wild flowers located near Middletown, Connecticut.
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  • Middletown, Connecticut

    Hike Wadsworth Mansion At Long Hill

    1 mi / 68 ft gain
    Wadsworth Mansion at Long Hill is a 1 mile loop hike that takes you past great forest setting located near Middletown, Connecticut.
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  • Cromwell, Connecticut

    Hike White Blaze Trail Loop

    2.2 mi / 196 ft gain
    White Blaze Trail Loop is a 2.2 mile loop hike that is good for all skill levels located near Cromwell, Connecticut.
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  • Cromwell, Connecticut

    Hike Red And Green Blaze Trail Loop

    1.6 mi / 91 ft gain
    Red and Green Blaze Trail Loop is a 1.6 mile loop hike that takes you by a river located near Cromwell, Connecticut.
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  • Middletown, Connecticut

    Hike Wadsworth Mansion Inner Trail

    0.9 mi / 42 ft gain
    Wadsworth Mansion White Oak Lane and Dolly Lane is a 0.9 mile loop hike that takes you past great forest setting located near Middletown, Connecticut.
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  • Middlefield, Connecticut

    Hike Camille's Way Trail

    2.2 mi / 180 ft gain
    Camille���s Way Trail is a 2.2 mile loop hike that takes you past great forest setting located near Rockfall, Connecticut.
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  • Middletown, Connecticut

    Hike Mattabesett Trail: River Rd To Bear Hill Rd

    9.3 mi / 1 ft gain
    Mattabesett Trail: River Rd to Bear Hill Rd is a 9.3 mile loop hike that takes you by a lake located near Middletown, Connecticut.
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  • Middletown, Connecticut

    Hike Asylum Reservoir Loop

    1.4 mi / 98 ft gain
    Asylum Reservoir Loop is a 1.4 mile loop hike that takes you by a lake located near Middletown, Connecticut.
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  • Middletown, Connecticut

    Hike Wadsworth Falls Trail

    3.6 mi / 360 ft gain
    Wadsworth Falls Trail is a 3.7 mile loop hike that takes you by a waterfall located near Rockfall, Connecticut.
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  • Middletown, Connecticut

    Explore Wadsworth Falls

    5.0
    0.25 mi
    When it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...
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  • Middletown, Connecticut

    Hike Smith Park Loop

    1 mi / 108 ft gain
    Smith Park Loop is a 1 mile loop hike that takes you past wildlife located near Middletown, Connecticut.
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  • Middlesex County, Connecticut

    Hike to Glen Falls

    5.0
    0.75 mi
    Accessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...
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  • Portland, Connecticut

    Hike Portland Reservoir Loop (Red Blazes)

    1.6 mi / 72 ft gain
    Portland Reservoir Loop (Red Blazes) is a 1.6 mile loop hike that takes you by a lake located near Portland, Connecticut.
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  • Portland, Connecticut

    Hike Reservoir, North Mulford And Del Reeves Road

    8.9 mi / 1 ft gain
    Reservoir, North Mulford and Del Reeves Road is a 8.9 mile loop hike that takes you by a lake located near Portland, Connecticut.
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  • Berlin, Connecticut

    Hike Pistol Creek

    2.3 mi / 127 ft gain
    Pistol Creek is a 2.3 mile loop hike that takes you by a river located near Berlin, Connecticut.
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  • Rocky Hill, Connecticut

    Hike Dividend Pond Lower Pond Loop

    0.4 mi / 26 ft gain
    Dividend Pond Lower Pond Loop is a 0.4 mile loop hike that takes you by a lake located near Rocky Hill, Connecticut.
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