Login | February 09, 2026
Pittsburgh Bound
PETE GLADDEN
Published: February 9, 2026
With all this crazy cold winter weather we’ve been enduring seems as though it’s about time to take a little trip to escape what appears to be a prolonged, and maybe for some of you an agonizing, 2026 winter season.
Yet reality for many of us is that we don’t have the where-with-all to pull off a spur-of-the-moment Jet Blue getaway to some far flung south-of-the-border beach.
And that brings me to today’s column.
So how about I let you in on a little weekend winter road trip that won’t break the bank nor require a prolonged auto journey?
It’s a place that, for those of you like myself who can’t get out of Dodge until spring, can be a real morale booster as we move into February.
And it just so happens to be a cool little one-tank trip that my girlfriend and I embark on round about every Valentine’s Day.
The place I’m suggesting is one of our nearest big city neighbors, Pittsburgh Pennsylvania.
Now stay with me diehard Browns fans.
If you’ve been purposely avoiding the black & gold’s hometown for a while you’re going to be pleasantly shocked at what a fun place Pittsburgh can be.
And that’s because of its accessible downtown, a downtown that lends itself to exploratory weekend walking excursions where you have the option of ducking in and out of the cold winter elements to dine, to shop and to enjoy some great winter sight-seeing…especially during the evening hours.
So let me give you a couple of the notable downtown Pittsburgh venues that make this a great place for wintertime urban walking excursions.
1) Market Square
Market Square, located smack dab in the middle of the city, is an open public space loaded with a variety of restaurants and specialty shops.
It’s located at the intersection of Forbes Avenue and Market Street and entails a pedestrian-only square that hosts numerous community events and festivals throughout the year.
Now I’m definitely not a shopper - nor a browser - but for some odd reason I really enjoy winter hiking in and out of the various shops that make up the Market Square during a cold winter’s Saturday afternoon.
And we always manage to find some great afternoon and evening dining later in the day whether it’s at the square or at the nearby strip district.
Do keep in mind though that there are limited parking spaces near Market Square, though there are plenty of garages in the area.
And that parking issue is exactly why we hotel right downtown such that we can walk everywhere.
2) PPG Place
If you’re looking for a change of pace in some wintertime aerobic activity merely head about a block south to skate at the beautiful PPG Place ice rink.
This iconic building, which resembles a massive crystalline sculpture, is the third tallest building in Pittsburgh and the tenth tallest in the state.
3) Point State Park
I’ve always loved visiting Point State Park, but honestly, something about a cold, clear and starry winter’s night just makes this venue exponentially more fabulous to stroll through.
So the park occupies a spit of land jutting out between the Allegheny and Monongahela Rivers - which makes for some truly dramatic scenery.
There you’ll find paved walking and biking paths, spotlessly clean restrooms and a plethora of benches where you can sit back and take in the sights.
It’s truly the perfect place to soak in the ambience of downtown Pittsburgh.
4) Walking routes in downtown Pittsburgh
Northshore Riverfront Trail is a 7.2 mile one-way asphalt trail that starts at the corner of North Franklin Street and Oxline Street and meanders along the Ohio and Allegheny Rivers.
Along it you’ll pass by the North Shore Riverfront Park, the West Penn Railroad Bridge and a host of amazing views of downtown Pittsburgh.
Strip District Trail is a flat 2.1-mile, paved section of the Three Rivers Heritage Trail, and it connects Point State Park to the 25th-33rd Street areas where you’ll encounter some of the city’s historic industrial remnants along with some cool old neighborhoods and a plethora of shopping and food venues.
So if you can’t get out of Dodge this winter season don’t despair, because there’s some pretty cool little winter getaways just around the corner - like Pittsburgh, PA.