The Best Trails in Pittsburgh, Pennsylvania (United States)

107 trails

(11)
Photo of Oakland, Greenfield and Squirrel Hill Photo of Oakland Short Loop Photo of Point State To Emerald View Trail
Show map

  • Oakland, Greenfield and Squirrel Hill

    Walking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    6.54mi
    Elevation +
    709f
    TrailRank
    86| Rating 5.0
    Photo ofOakland, Greenfield and Squirrel Hill Photo ofOakland, Greenfield and Squirrel Hill Photo ofOakland, Greenfield and Squirrel Hill

    I started this slightly longer walking or jogging trek at the Mary Schenley Memorial Fountain in Central Oakland at 40.44201°N and -79.95205°W. I walked along Schenley Drive crossing the Schenley Bridge at 40.44134°N and...

    This is a very good walk and quite easily done. I enjoyed the small sections with some gradient through Squirrel Hill. T...
    Trini Hiker

  • Oakland Short Loop

    Walking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    5.04mi
    Elevation +
    364f
    TrailRank
    85| Rating 5.0
    Photo ofOakland Short Loop Photo ofOakland Short Loop Photo ofOakland Short Loop

    I started this easy walk on a chilly winter evening in early January from the Forbes Field Outfield Wall along Roberto Clemente Drive at 40.44145°N and -79.95286°W. Turn right at the traffic lights at Schenley Drive and ...

    Great walking trail in the late Spring or early Summer months. Lots to see and do along the way.
    Trini Hiker

  • Point State To Emerald View Trail

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    12.45mi
    Elevation +
    1765f
    TrailRank
    83| Rating 5.0
    Photo ofPoint State To Emerald View Trail Photo ofPoint State To Emerald View Trail Photo ofPoint State To Emerald View Trail

    I started this very interesting trek from “The Point” at Point State Park in downtown Pittsburgh. The western terminus of the Great Allegheny Passage sits at 40.44190°N and -80.01323°W and is clearly labelled. This park ...

    This trail is one of the challenging trails in the Pittsburgh area but well worth doing.
    Trini Hiker

  • To McKees Point and Beyond

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    24.43mi
    Elevation +
    699f
    TrailRank
    83| Rating 5.0
    Photo ofTo McKees Point and Beyond Photo ofTo McKees Point and Beyond Photo ofTo McKees Point and Beyond

    I started this moderate length walking trek at the corner of Forbes & Murray Avenues in Squirrel Hill at 40.43803°N and -79.92303°W. I walked along Murray Avenue and turned onto Hazelwood Avenue at 40.41972°N and -79.928...

    It's a good trail to get out and do. The only real issues I found were the long sections in direct sunlight exposure and...
    Trini Hiker

  • Create your Trail Lists

    Organize the trails you like in lists and share them with your friends.

    Get Wikiloc Premium Upgrade to remove Ads
    Create your Trail Lists Create your Trail Lists

  • Greenfield To Schenley Park

    Walking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    8.39mi
    Elevation +
    968f
    TrailRank
    83| Rating 5.0
    Photo ofGreenfield To Schenley Park Photo ofGreenfield To Schenley Park Photo ofGreenfield To Schenley Park

    This short walk explores Schenley Park but starts in Greenfield. I started this trek at the traffic lights at the Alger Street, Ronald Street, Beechwood Boulevard, and Greenfield Road intersections at 40.42719°N and -79....

    I was lucky enough to have seen a couple of white tail deer along this trek. It is relatively easy to do but, depending ...
    Trini Hiker

  • Squirrel Hill to McKeesport

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    22.08mi
    Elevation +
    719f
    TrailRank
    83| Rating 5.0
    Photo ofSquirrel Hill to McKeesport Photo ofSquirrel Hill to McKeesport Photo ofSquirrel Hill to McKeesport

    I started this moderate trek at the corner of Forbes & Murray Avenues in Squirrel Hill at 40.43803°N and -79.92303°W. From here a couple options exist. For the adventurous you can start walking along Murray Avenue. You c...

    It's worth doing. The most interesting part of the trail was the leg between the Waterfront in Homestead right to the cr...
    Trini Hiker

  • Exploring Schenley Park

    Walking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    6.39mi
    Elevation +
    627f
    TrailRank
    83| Rating 5.0
    Photo ofExploring Schenley Park Photo ofExploring Schenley Park Photo ofExploring Schenley Park

    Schenley Park is a 456 acre park in the city of Pittsburgh. The park borders Oakland, Squirrel Hill and Greenfield. It contains many trails as well as natural and man-made attractions. Because of the physical size of the...

    It is indeed a very nice area for walking. There's ample wildlife sightings along the trails. The deer appear un-phased ...
    Trini Hiker

  • Four Rivers and Five Trails

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    39.17mi
    Elevation +
    883f
    TrailRank
    80| Rating 5.0
    Photo ofFour Rivers and Five Trails Photo ofFour Rivers and Five Trails Photo ofFour Rivers and Five Trails

    This trail is one of the most entertaining that I have done in some time. It has a little of everything for everyone. It was marked as a hiking trail but it can be biked. I prefer to hike it to experience all that the tr...

    This is a very nice adventure, for a cyclist! Long sections of the trail has nothing to see. I didn't enjoy the section ...
    Trini Hiker

  • Three Trails, a River, and a Park

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    17.61mi
    Elevation +
    906f
    TrailRank
    80| Rating 5.0
    Photo ofThree Trails, a River, and a Park Photo ofThree Trails, a River, and a Park Photo ofThree Trails, a River, and a Park

    I started this interesting yet moderate length walking trek at the corner of Forbes & Murray Avenues in Squirrel Hill at 40.43803°N and -79.92303°W. I walked along Murray Avenue and turned onto Hazelwood Avenue at 40.419...

    I was fortunate enough that on the day I did this trail there were few cyclists and many more walkers along the Three Ri...
    Trini Hiker

  • Emerald View Trail Short Loop

    Hiking
    Save to a List
    Author
    Sherwin P. Cedeno
    with Trini Hiker
    Distance
    2.31mi
    Elevation +
    344f
    TrailRank
    52| Rating 5.0
    Photo ofEmerald View Trail Short Loop Photo ofEmerald View Trail Short Loop Photo ofEmerald View Trail Short Loop

    The Emerald View Trail is just about the most enticing trail that I have encountered in Pittsburgh. It's an actual hiking trail that's full of everything you need and so much more. You can start the trek at the "Points o...

    This trail is challenging. I did this one after rainfall and it was very slippery. I think that it should be started wit...
    Trini Hiker

  • Frick Park Meetup

    Hiking
    Save to a List
    Author
    JLR44
    Distance
    4.43mi
    Elevation +
    2185f
    TrailRank
    24
    Photo ofFrick Park Meetup

    This is a 4.4. mile hike in Pittsburgh's Frick Park that takes in most of the real estate in this city park. Approximate hiking time is 2 hours 00 minutes.

  • Square to the Breeze

    Walking
    Save to a List
    Author
    PWiegman
    Distance
    2.04mi
    Elevation +
    157f
    TrailRank
    22
    Photo ofSquare to the Breeze Photo ofSquare to the Breeze Photo ofSquare to the Breeze

    A two-mile loop walk through the northern end of Frick Park. It begins and ends in the Regent Square neighbor and at the apex touches the Point Breeze neighbor.

  • Dinky Bridge

    Walking
    Save to a List
    Author
    PWiegman
    Distance
    2.13mi
    Elevation +
    138f
    TrailRank
    20
    Photo ofDinky Bridge

    An hour's walk on the east side of Frick Park in the Regent Square neighborhood. The Dinky Bridge Trail portion is used by mountain bikes and includes a tilted bridge over a small ravine. It makes for an interesting cros...

  • Allentown Urban Hike 9 24 16

    Walking
    Save to a List
    Author
    JLR44
    Distance
    3.21mi
    Elevation +
    486f
    TrailRank
    19

    Urban Hike led a 3 hour hike through the streets of the Allentown neighborhood of Pittsburgh, several of the trails in Emerald View Park, and finally down the Pittsburgh steps near Grandview Park. We stopped at the "Work...

  • Frick Park Shorty

    Walking
    Save to a List
    Author
    PWiegman
    Distance
    1.05mi
    Elevation +
    82f
    TrailRank
    16
    Photo ofFrick Park Shorty Photo ofFrick Park Shorty

    Easy mile-long walk 1/2 woodlands and 1/2 quiet residential streets beginning at the Biddle Building/Clay Tennis Courts parking lot.

  • Pgh

    Road Bike
    Save to a List
    Author
    nukonamo
    Distance
    15.44mi
    Elevation +
    1647f
    TrailRank
    16

    road bike trip around downtown. Its an easy ride, but beware of the hill leading up to the 31st bridge.

  • Highland Park Ramble 8 2 17

    Walking
    Save to a List
    Author
    JLR44
    Distance
    1.52mi
    Elevation +
    121f
    TrailRank
    12
    Photo ofHighland Park Ramble 8 2 17

    Today's ramble started at the Rhododendron Shelter and went behind Carnegie Lake, the swimming pool, up to and around the Bigelow Trail, and then back again.

Advanced Filters

Filter by recording month or date. Find trails only from people you are following.

Get Wikiloc Premium Upgrade to remove Ads
Advanced Filters Advanced Filters