Boston’s Freedom Trail is annoyingly great. Could Philly do the same by 2026?

I went to Boston for the first time last weekend and I’m sorry to report that it wasn’t terrible. In fact, I had a pretty good time and I’m saltier than a bowl of clam chowder about it.

Over two days, my husband and I spent a majority of our trip walking Boston’s Freedom Trail, a 2.5-mile path of bricks, red paint, and bronze plaques on Boston’s sidewalks (yes, we could have done it in one day, but we were on vacation and drinks were involved).

Created in 1951, the trail takes you to 16 historic sites around the city, from Boston Common to Bunker Hill. You can do it self-guided, as we did, or join a tour with a guide in colonial garb. Some sites charge admission, but walking the trail yourself is free.

As we followed the path, exploring old cemeteries and the USS Constitution (a.k.a. “Old Ironsides”), I couldn’t help but wonder, “Why doesn’t Philly have one of these trail things?”

Along the way, we also saw many artists busking. In Boston Common, there was a man in a porkpie hat on a tiny spinning platform playing Bob Dylan’s “Blowin’ in the Wind” on a device covered in horns and drums that he’d labeled the “Peace Wave Generator.”

Just outside of the Old North Church, we talked with a woman playing the glass armonica, a musical instrument that was invented by Benjamin Franklin, but one which I’d never actually seen played before.

And in the car-free pedestrian zones around Faneuil Hall and Quincy Market, there were always public performances happening, from high school marching bands and drum lines to a woman playing the violin in a ball gown and a dude in a bear costume playing the keytar.

Admittedly, some performers were better than others, but as I dropped dollar bills in their buckets, I couldn’t help but wonder, “Why doesn’t Philly have this many buskers?” I asked myself the same question after visiting New Orleans last year.

I love Philly, probably to a degree that’s unhealthy, because it will break your heart in many ways, many times. Yet it remains my favorite U.S. city because of the experiences, people, and history that surround us here.

I still get goose bumps when I see Independence Hall, even though our newsroom looks right over it. I’m still fascinated by Philadelphians, whose blunt honesty and unique talents never cease to amaze me. And I still live for the experiences I never expect, like singing with a stranger on the street or having a Benjamin Franklin reenactor hold the door for me at Wawa.

But there are always things we could do better, especially as 2026 approaches and people from across the country and around the world will come here for the nation’s 250th birthday and the World Cup.

Philadelphia needs to make it easier for tourists to experience our history and our people, so outsiders can understand why we love it here, and we can bask in their envy.

First, Philly needs its own version of the Freedom Trail. Of course, our city is already filled with talented tour guides who are great ambassadors, but not everybody has the foresight or money to schedule a tour.

There are some self-guided walks available for free online, like the Constitutional Walking Tour (which made me snicker since constitutional can be a euphemism when morning is put in front of it).

The tour isn’t bad — it’s a three-mile walk around Center City and Old City with 30 stops at places like Independence Hall and Elfreth’s Alley — but it’s a bit outdated. It includes Signers’ Walk, a series of plaques featuring members of the Continental Congress embedded in the sidewalk on Chestnut Street, at least 12 of which have been stolen. And there’s a stop on the tour at the Philadelphia History Museum at the Atwater Kent, which closed in 2018.

But what Philly really needs is a physical trail like the Freedom Trail, so people have a clearly designated path to follow. Humans love a good journey, and giving people the means to set off on one of their own in our city could make for a memorable experience, as it did for us in Boston.

Embedding a path in the sidewalk and streets also helped keep me off my phone and in the moment. I didn’t need Google Maps to tell me how to get to the next stop on the Freedom Trail, I just looked down at the path on the sidewalk.

Philly’s version of the Freedom Trail could be called the Liberty Walk or Independence Path (other ideas suggested by users on X, the platform formerly known as Twitter, include the Streets of Philadelphia, Revolution Road, Freedom Jawnt, and the “Yo! I’m walkin’ here! trail”).

Philadelphia also needs to do a better job at bringing artists into public spaces. Street performers give a city character and break us out of the everyday.

I know Philly is filled with uniquely talented people willing to perform in public. Heck, I’ve written about a lot of them, from David Puryear and his saxophone, “Miss Nasty,” who’ve been staples on Market Street in Old City for years, to Philly street poet Marshall James Kavanaugh.

You can usually find buskers outside Reading Terminal Market and City Hall but their numbers are nowhere near what I’ve seen in some other U.S. cities.

The question of why Philadelphia seemingly has so few buskers has been asked several times on various Philly Reddit threads over the years, with answers ranging from “there’s not an established area for busking” to “Orpheus himself could not melt the cold hearts of the Philadelphian with music. That is why the scene is dead here … no appreciation.”

To gain further insight, I talked with Kavanaugh, the Philly “Dream Poet for Hire” I profiled a few years ago. He often sets up his folding table, chair, and typewriter in Rittenhouse Square and has busked in other U.S. cities like Santa Fe, Denver, and New York.

Kavanaugh said he doesn’t need a permit to busk in Philly and the barriers here aren’t higher than in other cities.

“It kind of falls under freedom of speech, as long as you’re not blocking a sidewalk, you’re welcome to do whatever you want,” he said.

The Mayor’s Office did not respond by deadline to a request seeking any rules and regulations governing busking in Philadelphia, nor did Independence National Historical Park, which oversees Independence Mall (a large, grassy area where buskers are never seen). SEPTA does require a permit to busk in its concourses and busking must be done in designated areas.

Kavanaugh said he worried when he started busking here that Philadelphians might be closed off to the idea.

“But I was very pleasantly surprised. People in Philly were very open and excited and very sweet,” he said. “I think we love the underdog, so we see the guy who’s pitching his craft on the corner and we’re like, ‘That guy is not Pablo Picasso, he’s not making a million doing what he’s doing, but he’s chasing a dream and that’s exciting.’”

Perhaps one of the biggest roadblocks to a more vibrant busking scene in Philly, Kavanaugh said, is the city’s lack of pedestrian-only malls, plazas, and streets. Philly doesn’t have a defined pedestrian hub (like the area around Faneuil Hall in Boston) where buskers can set up and large crowds can gather.

“I think pedestrian and foot traffic areas create that perfect space for performers because everyone stops as they’re walking by,” he said.

The more I travel across the country and abroad, the more compelled I am to join the chorus of people calling for a car-free, pedestrian-only zone in Philly. It feels like we’re already behind the ball on this, and if there was ever a moment to get started it’s now, for 2026.

Just like we need our own version of the Freedom Trail to introduce tourists to our history, we also need a defined pedestrian zone to introduce visitors to our people and to allow for communal experiences between locals and out-of-towners.