Philadelphia Neighborhood Scouting: First Impressions of Manayunk, Fairmount, Chestnut Hill & More

Philadelphia city scouting trip: complete. Is it going to be home? To be determined.

After a smidge over 13 years in D.C. and a layover in my hometown, I’m now on the search of my next true home base. Somewhere that feels alive, inspiring, and maybe even a little forgiving when it comes to parallel parking. Philly landed high on my shortlist — so I packed my car and took the mini-roadtrip (about an hour and a half) to the City of Brotherly Love and spent a weekend exploring its neighborhoods.

While I’m not entirely sure if Philly is “the one” yet, the city surprised me in some good ways — the warmth of its people and strong sense of city pride and community, the mix of grit and charm (pros and cons here, to be honest), and the fact that cars actually stop when you’re trying to cross the street (I KNOW. Very not DC-like). Here’s how each neighborhood stacked up in my humble opinion:

Manayunk: Philly-Lite with Floating Umbrellas

Manayunk feels like the starter kit of city living. A row of boutique stores, coffee shops, and restaurants line Main Street, punctuated by murals and those whimsical floating umbrella art installations. It’s adorable, approachable, and just urban enough to feel like you’ve left the suburbs behind. In reality, it’s kind of “Philly training wheels” — a landing spot for college grads or newcomers dipping their toes into city life without fully committing.

Fairmount: History Meets Brick-Row Elegance

Fairmount swept me off my feet with its polished brick row homes, tree-lined blocks, and stylish patios dressed with seasonal décor. But Philly never lets you get too comfortable: right in the center of the neighborhood sits Eastern State Penitentiary, once the most famous prisons in the world and now a museum. Its looming stone walls are a reminder that Philly loves its juxtapositions — beauty and darkness, refinement and rawness. Somehow, it works.

Spring Garden: Fairmount’s Edgier Twin

Just next door, Spring Garden feels like Fairmount’s slightly rougher sibling. The bones are similar — row homes, leafy streets — but the polish fades. Some blocks have charm, others feel more unpredictable, especially after dark. Still, there’s character here, and I can see why people love the location, a stone’s throw from Center City but with a (slightly) quieter vibe.

Center City: Big-City Hub Bub

Center City is exactly what you’d expect. Towering skyscrapers, crowded sidewalks, and the buzz of commerce. Think “Philly does NYC-lite.” It’s fun for dinner, rooftop bars, and people-watching, but not somewhere I’d personally want to live. Too much hubbub, too much traffic, too little calm. Still, the energy is undeniable, and for many, that’s the whole point.

East Passyunk: Tattoos and Grit with a Side of Cool

Walk through East Passyunk and you’ll catch whiffs of old-school South Philly blended with a modern indie spirit. The neighborhood’s roots lie in its early 20th-century row homes — you can almost imagine immigrant families spilling onto stoops in a scene straight out of Dublin or Naples. Today, the vibe is grittier and cooler: edgy restaurants, quirky plant shops, craft cocktails, and bike stores that double as community hubs. Honestly? I’d need at least seven more tattoos to truly belong here.

Fishtown: Trendy… with Zombies

Fishtown has become one of Philly’s buzziest neighborhoods, and it shows. Breweries, art galleries, and coffee roasters spill into renovated warehouses, while new condos rise quickly. But it’s also ground zero for Philly’s opioid epidemic, a reality that hits hard when you see people struggling just steps from a trendy brunch spot. The contrast is jarring. Add in the fact that it’s a bit farther north than I’d like, and I think Fishtown and I will stay casual acquaintances.

Mt. Airy: The Sleepy City-Suburbs

Mt. Airy lives in the liminal space between city and suburb. Streets are leafy and quiet, lined with 1940s and 50s homes alongside weathered row houses. There’s a genuine community feel here, bolstered by local markets and coffee shops. But it’s sleepy — the kind of place that makes you wonder if living here counts as “being in the city” or if you’re cheating. Still, for those who want more space and peace without leaving Philadelphia entirely, it’s an appealing middle ground.

Chestnut Hill: Cobblestones and Farmers Markets

Ah, Chestnut Hill. You cute little cutie. Cobblestone streets, boutique markets brimming with local produce, and historic townhomes dating back to the 1800s. It feels like a small-town village that just happens to be tucked into a big city. The charm is irresistible. The price tag? Less so. Million-dollar homes are the norm here, which makes me wish for just a slightly more affordable version — crackhead or two included.

Final Thoughts

So, where did I fall hardest? Chestnut Hill and Fairmount stole the show. But what struck me most is that every neighborhood has its own personality — from polished to gritty, sleepy to buzzing.

And while I’m still not sure if Philly is my forever city, I walked away a bit more impressed than I thought I would be. The people were kind, conversations flowed easily, and the city felt more welcoming than I expected. Philly lived up to its name: a city of Brotherly (and Sisterly) Love.

Thinking about a move yourself? Check out my City Scouting Guide for the exact questions I used to compare neighborhoods and decide what really matters when choosing a new home base.