The Ultimate Trail to Tavern 3-Day Weekend in Philadelphia

Philadelphia might be best known for cheesesteaks and ‘Brotherly Love’, but this trail to tavern city is working hard to earn a new nickname: America’s Best Beer City. Philadelphians love drinking and brewing beer so much that they’ve dedicated an entire week to the craft each year. For outdoor enthusiasts looking to pair ales with hiking trails, America’s 5th biggest city has a ton to offer—if you know where to find it. From trekking on the Appalachian Trail to exploring the wilds of the Wissahickon, you can spend time in nature without even leaving the city limits. Follow this long-weekend itinerary for some of the best outdoor activities (and the best beer!) that the city has to offer.

Day One

No visit to the America’s birthplace is complete without seeing a landmark steeped in history. Kickoff your day at Valley Forge National Historical Park, where General George Washington’s Continental Army set up camp during the original British Invasion in 1777. Take some time to tour Washington’s headquarters then go forth to conquer Mount Misery and Mount Joy. It’s just over 4 miles (if you climb both) of lush, wooded trails. You’ll pass a dilapidated, old bottling plant, a covered bridge from the 1800s and eventually pop out at the summit of Mount Joy. America the beautiful, indeed! On your way back from Valley Forge, grab a beer in the Philly neighborhood of Manayunk. Its vibrant Main Street is home to more than 60 funky shops and restaurants, and the most scenic spot for lunch is Manayunk Brewing Company. Order a flight and hang out on the massive riverside deck overlooking the Schuylkill River. After a cold drink, make your way to Center City and grab lunch at the Reading Terminal Market. This farmer’s market has all kinds of restaurants, ranging from Thai food to burger joints, but it’s pretty much a requirement to get yourself a cheesesteak when in Philly. By George! Pizza, Pasta and Cheesesteaks is one of the best. It’s also a good option to pick up a slice of pizza if cheesesteaks aren’t your thing. After filling up at the market, take it easy and rent a bike from Philadelphia’s Indego bike share. Saddle up and cruise on one of America’s best urban trails: the Schuylkill River Trail. Take in views of the Philadelphia skyline as you ride along the water, and continue up the riverfront to the Philadelphia Art Museum. Movie aficionado or not, channel your inner Rocky Balboa as you ascend the steps. And if you throw up your arms in celebration at the top, we won’t judge. To get a true education on Philadelphia’s beer scene, head straight to the source. Tucked down a dark, inconspicuous alley in the heart of the city, you’ll find McGillin’s Olde Ale House. As Philadelphia’s oldest continuously operating bar, the beer’s been flowing here since 1860 and hasn’t stopped since - not even during Prohibition (hence the dark, inconspicuous alley). McGillin’s is still the rowdiest ale house in town, but they’re serious about great beer. You’ll find 30 beers on tap, with a focus on eastern Pennsylvania breweries and three signature brews: McGillin’s Real Ale, McGillin’s Genuine Lager, and McGillin’s 1860 IPA. McGillin’s has typical bar fare (think nachos and mozzarella sticks), but also has a full menu with everything from pizza and salad to full-on entrees like chicken parm, meatloaf, and a German sausage platter.

Where to Stay

After a long day, head to the revitalized Fishtown neighborhood to get a good night’s sleep. This up-and-coming neighborhood currently has just one hotel—a four-room boutique called Wm. Mulherin’s Sons. Housed in a restored 1800s whiskey distillery that bore the same name, Muhlerin’s shares its space with one of the city’s best restaurants and is walking distance from the best breweries and taphouses around.

Day Two

After a potentially long night at McGillan’s, you may need a little pick-me-up to start day two. Luckily, just a couple blocks from the hotel is the Gryphon Coffee Company. Check out the local art on display while you sip your latte and then head out to escape the city’s hustle and bustle with a mountain bike ride or trail run in Wissahickon Valley Park. Just beyond the city’s art museums, this forest haven is technically within city limits but feels worlds apart. Out of eye and earshot of Philadelphia, explore some of the 50 miles of rugged trails winding through the gorge. Look for remnants of the old milling industry: crumbling dams, preserved homes and roadhouses, and the only covered bridge left in Philadelphia. Despite the name, Forbidden Drive is one of the easiest trails at the park, with a gentle grade and wide gravel path. The 5.35-mile route follows the Wissahickon Creek from one end of the park to the other, and is popular for biking or an easy trail run. For more of a challenge, try the 4.39-mile White Trail. You’ll find technical singletrack with some steep sections along the eastern side of the park. Once you’ve worked up a sweat, head to Philadelphia’s Kensington neighborhood for a free tour and tasting at Philadelphia Brewing Company. Every Saturday, this local brewery opens their doors to the public from 12-3 p.m., and the vibe is totally casual—no reservations necessary. You’ll learn about the brewing process and they say you might even pick up a few useful tidbits of information as well. Try year-round classics like the Kenzinger, a crisp, light golden beer that you’ll find all over town or the PHL Session IPA if you like it hoppy. From Philadelphia Brewing Company, grab another Indego bike and head down Christopher Columbus Blvd. to Spruce Street Harbor Park on the Delaware River Waterfont. Grab a bite to eat at one of the vendors or at the floating (that’s right, floating) restaurant, and then hang out in one of the colorful handmade hammocks. You can also take a walk along the boardwalk, play one of the many games available (bocce ball, life-sized chess or Connect Four), or play traditional boardwalk games housed in converted shipping containers. This pop-up park is open from May - September. From the park, go about three miles north for a drink at the Evil Genius Beer Company, an old auto body shop turned innovative beer lab. The ridiculous names and unique flavor combinations make for a memorable pit-stop. Try the Purple Monkey Dishwasher, a chocolate peanut butter porter, or the I Love Lamp, a pineapple Hefeweizen. And if you need a 90’s video game fix, a vintage Sega Genesis is calling your name (that’s the actual game console, not a beer, FYI). They’ve got a kitchen too, so stock up on hoagies and sloppy joes, too. The night doesn’t have to end there: less than a half-mile walk from Evil Genius, get a taste of Germany on Fishtown’s bustling Frankford Avenue. The massive indoor-outdoor beer garden at Frankford Hall is the place to challenge your friends to a round of Jenga or foosball. Go big and order a giant one-liter stein of German (or local) beer, and pair it was a Bavarian soft pretzel the size of your face.

Day Three

For your last day, we’ve got one more hike for you, and it’s a toughie. Drive 90 mins to the town of Hamburg and jump on the 8.7-mile Appalachian Trail circuit to the Pinnacle and Pulpit Rock. The high point of the AT in Pennsylvania, Pinnacle and Pulpit Rock’s expansive vistas make this steep, rocky trek worthwhile.

Another Option

If you want to get a different perspective on the city, head back over to the Schuylkill River and rent a kayak or paddle board from Hidden River Outfitters. Located at the Walnut Street Dock, Hidden River also runs tours a couple days a week during the summer. Paddlers of all levels will feel comfortable on the waterway, and the outfitter offers moonlight kayak tours and movie nights if you end up staying for one more night. Top off an adventure-filled weekend than one last pint at Yards Brewing, a Philadelphia mainstay since 1994. Rent an Indego bike and follow the paved East Coast Greenway to this riverside brewery. Free tours are offered from 12-4 p.m. and you should take it. You’ll learn why Philadelphia water is tops for beer production and how Thomas Jefferson’s Tavern Ale is made (hint: it’s a historically accurate beer made from the original recipe that ol’ TJ brewed at Monticello). When it comes to food, Yards has you covered - they feature a different local food truck every Saturday, while Oink & Moo BBQ is there every Sunday. You can also load up a bowl of homemade bison and beef chili, nachos, or a sandwich to fill your stomach before calling it a weekend. Just make sure you get there before last call (usually around 7 p.m.). Don’t say we didn’t warn you: it only takes a couple days to fall in love with a place like Philadelphia. Between the tasty beer, extensive trail network, and historical landmarks, the city of Brotherly Love offers something for everyone. Don’t be surprised if you start planning your next trip on the ride home. Originally written by RootsRated for Toad&Co. Featured image provided by Montgomery County Planning Commision