Philadelphia Boys Trip Weekend Getaway: 18 Things Men Will Love To See And Do In Philly!

Going on an adventure with the boys is an enticing thought and one of the most under appreciated destinations for a boys trip is Philly. It's literally the "City of Brotherly Love" and is packed with craft beer, artisinal food, history, movie sites and more. We think Philadelphia is a hidden gem that more guys should know about. There are tons of things to do here, from restaurants and bars to the obvious long list of historical sites, and of course, this is where Rocky was from, so there are plenty of movie sites to visit, too. But if you're looking to get away with the boys, Philadelphia also offers a ton of unexpected places and experiences to keep you occupied and happy. So, let's take a look at some of the best things to do do in Philly for men!

Run Up the Stairs of the Philadelphia Museum of Art

This is pretty much a required thing to do for a guys weekend in Philadelphia, so get ready. We're going to run in the steps of Rocky up to the Philadelphia Museum of Art and then take photos with the statue located adjacent to the steps. This is actually a great museum but sweaty guys shouting their favorite Rocky quotes is a great way to kick off your guys weekend!

Grab a Cheesesteak and Argue About Who's Is Better

While Philly locals all have their own favorite cheesesteak place, and many of them chose places other than the famous Geno's Steaks and Pat's King of Steaks, this is a required stop when you visit here.  The two properties are located on the same corner of South 9th Street and Passyunk Ave so this is an easy way to get your debate on experience part of Philly's legendary food culture.

If cheesesteaks aren't your style, don't worry! This is a SANDWICH CITY and someone has the right combo for you, so keep searching :)

Reading Terminal Market

This historic market is a food lover's paradise and the perfect spot to fuel up before a day of activities or recover from the previous night's festivities. Housed in a former railroad terminal since 1893, Reading Terminal Market offers everything from classic Philly cheesesteaks and roast pork sandwiches at DiNic's (voted "Best Sandwich in America" by the Travel Channel) to Amish breakfasts and local specialties. The best strategy is to divide and conquer – have each person in your group get something different and create your own food-sharing feast at the communal tables.

Visit the Eastern State Penitentiary

At one point, Eastern State Penitentiary was the most famous and expensive prison in the world. Today, though, it stands as a crumbling reminder of a prison system that lives on only in our legends and stories of famous criminals like "Slick Willie Sutton and Al Capone. It is also the first of a generation of prisons designed as a true penitentiary ... a detention facility designed to inspire it's residents to become penitent in true regret due to the foreboding architecture and strict discipline.

Catch a Game (seriously, Philly Sports are all Awesome!)

While I dream of one day attending a Flyers game, I'd be more than happy to cheer on the Eagles or Phillies too. Oh yeah, and the Sixers are here too. :) Philadelphia is absolutely one of the biggest destinations for sports fans, and win or lose, the fans here are among the fiercest sports fanatics in the US, so it might just be safer to cheer for the home team instead.

Beer Tour

Philadelphia's craft beer scene rivals any major city, with a collection of world-class breweries all within easy reach of downtown. Start at Yards Brewing Company, Philadelphia's largest brewery, where you can tour the facility and sample their revolutionary ales inspired by founding fathers' recipes. From there, hit up Love City Brewing in the Spring Arts district and finish at Philadelphia Brewing Company in Kensington – each offering unique takes on classic styles and innovative new brews in distinctly different neighborhood settings.

McGillin's Olde Ale House

Step into Philadelphia's oldest continuously operating tavern, where the beer has been flowing since 1860 and the walls are literally covered with historical artifacts from the city's past. McGillin's is more than just a bar – it's a living piece of Philly history that serves up excellent pub fare and features 30 beers on tap, including their own McGillin's Real Ale. The place really comes alive on weekend nights with a diverse crowd of locals, students, and visitors all mingling in an atmosphere that perfectly balances historic charm with lively sports bar energy.

Liberty Bell & Independence Hall

No boys' trip to Philadelphia is complete without a quick dive into American history at Independence Hall, where you can actually stand in the room where the Declaration of Independence and U.S. Constitution were debated and signed. While tickets are required during peak season, they're free, and the guided tours last just 30 minutes – perfect for getting your cultural fix without spending the whole day on history. The guides bring the room to life with fascinating stories about the founding fathers' heated debates and power struggles that shaped America.

More Ideas For A Philly Guys Getaway!

There's so much to do in Philadelphia that it's sometimes surprising that it's a forgotten city sandwiched between New York and Baltimore/Washington. Today, though, Philly has an amazing food scene, tons of craft beer, and even a handful of distilleries. Here's 10 more ideas for guys looking to plan the ultimate boys trip or guys weekend getaway.

Visit Franklin Institute

One of America's oldest and best science museums, featuring interactive exhibits, an IMAX theater, and a giant walk-through human heart. Perfect for guys who love technology and hands-on experiences.

South Street Bar Crawl

Hit up iconic spots like Tattooed Mom's, Bob & Barbara's (home of the citywide special - a shot and a beer), and Bridget Foy's along this vibrant street known for its eclectic nightlife.

Tour the U.S. Mint

See where America's coins are made and learn about the minting process. It's free and surprisingly fascinating, especially for history or engineering buffs.

Go-Karting at Speed Raceway

Indoor electric karting in nearby Horsham offers high-speed racing on a professional-grade track. Great for adding some adrenaline to the trip.

Penn's Landing Waterfront

Check out seasonal events, concerts, and festivals along the Delaware River waterfront. In winter, there's ice skating; in summer, there are beer gardens and outdoor movies.

Poker Night at Rivers Casino

Try your luck at Philadelphia's waterfront casino, featuring table games, sports betting, and multiple restaurants and bars.

FDR Park Disc Golf

For something more active, this 18-hole disc golf course in South Philly offers a fun outdoor activity, especially if you need some fresh air after too many cheesesteaks.

Schuylkill River Trail Bike Ride

Rent bikes and cruise along the scenic riverside trail, with great skyline views and stops at Boathouse Row. Can be combined with a visit to the Philadelphia Zoo.

Axe Throwing at Urban Axes

Located in Kensington, this BYOB venue offers a unique competitive activity perfect for group entertainment. They provide instruction and run mini-tournaments.

Live Music at Underground Arts

This gritty, industrial-style venue in the Callowhill neighborhood hosts rock shows, comedy nights, and other performances in an authentic Philly atmosphere.

It's a city that's got enough that you can make what you want of it, but don't ignore it when you make plans this year!