Top Trail Towns: Philadelphia, PA

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Many Americans think of Philadelphia as the place our nation was born, where our nascent country declared independence from colonization and the earliest conversations about U.S. governing and law took place. For those visiting from elsewhere in the States, it’s perhaps a rite of passage to pay homage to our nation’s origins.

However, Philly locals know that another kind of freedom abounds here: green space. The city has an ornate park system with singletrack-running opportunities in several places within city limits, and even more in the surrounding metropolitan area.

Says Bob Reynolds, a long-time member of the local trail-running club, the Wissahickon Wanderers, “Although I’ve been here all my life and running competitively for 45 of those years, I am still impressed with how the park system in Philadelphia can quickly transport you from a sometimes gritty urban environment to quiet, clean wooded trails. It is an oasis that recharges my energy.”

So, if you come for the history, you’ll want to stay for the dirt.


> Wissahickon Valley Park / More than 50 miles of trails await in what locals call “The Wiss,” a park encompassing Wissahickon Creek in northwest Philadelphia. Forbidden Drive is a wide, flat, dirt doubletrack that runs next to the creek, and singletrack takes off from it in every direction, spiking up and down the park’s short but steep hills. The Wiss is Philly’s crown trail jewel.

> Pennypack Park / Located northeast of downtown but within the Philly city limits, Pennypack Park is a narrow park following Pennypack Creek to the Delaware River. There’s a paved bike path that runs the approximate eight-mile length of the park, with dirt doubletrack next to it and a variety of singletrack snaking into and out of the park’s mature deciduous forest.

Photo: Steve Boyle


> Wissahickon Trail Classic / This 10-ish-kilometer trail race held in Wissahickon Valley Park is a popular event that tackles the park’s hilly terrain. It had more than 500 finishers in 2015.

> Sloppy Cuckoo Trail Runs / These unusually named 10K, half-marathon and marathon races take place in Philly’s Pennypack Park. You can run a whole trail marathon within city limits!


> Get There / Fly direct into Philadelphia International Airport. Or, since Philly is easily linked with New York, Baltimore and Washington, D.C., hop aboard an Amtrak train. Use the Southeastern Pennsylvania Transportation Authority’s bus and rail service to make your way around town. A rental car helps for the trailheads outside the city.

> Play Tourist / Visit Independence National Historical Park, where you can see the Liberty Bell and Independence Hall. Check out the Franklin Institute, which has been a science museum since—ahem—1824. Off the tourist path, but a delight if you’re a literature buff, is a visit to Charles Dickens’s pet raven, Grip, which has been taxidermied since its death in 1841. Grip, said to have also inspired the writing of Edgar Allan Poe, is housed in the Free Library of Philadelphia’s Rare Book Department.

> Take Note / While winter can be blustery in Philly, locals still trail run! Bundle up for below-freezing temperatures and wind, and be prepared for ice and maybe snow on the trails.


63 Number of parks managed by Philadelphia Parks and Recreation, totalling 10,500 acres—more than 10 percent of Philadelphia County’s land area—making it one of the largest urban park systems in the U.S.

1776 Year the Declaration of Independence was famously signed in Philadelphia. In 1787, the United States Constitution was also signed there.

This article originally appeared in our December 2015 issue.

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