Travel Spotlight: A Weekend In Pittsburgh

Mike Archer (1)

Like a Phoenix rising from the ashes, the City of Pittsburgh in recent decades has transformed from a gritty industrial city with crumbling factories, into a high-tech, hip urban metropolis.  It is a city, I recently had the opportunity to visit and fall in love with.

In recent years, Pittsburgh has become a top destination for weekend travel. The city, with its rich history and friendly Midwestern hospitality, is home to world class cultural venues, major sports teams, top Universities, great restaurants and unique activities you will not find in other U.S. cities.  It comes as no surprise that the charm and beauty of Pittsburgh has placed it on the top of many “Best Places” lists and is a perfect place to visit on your next weekend adventure.



Pittsburgh is a compact city centered around its Downtown, Business, Cultural and Strip Districts; with vibrant neighborhoods flanking it on either side of the rivers.

Along the Monongahela River sits the Southside.  Here you will find iconic Station Square and the Monongahela Incline, historic Southside Flats and the new Southside Works.

Across the Allegheny River you will find the Northside which includes: North Shore, Allegheny Center, Allegheny West, Heinz Field and PNC Park.

East of the city is where you will find the eclectic and upscale neighborhoods of Oakland (home to the University of Pittsburgh and Carnegie Mellon University), Shadyside, Squirrel Hill, Highland Park (home to the Pittsburgh Zoo), Schenley Park and Frick Park.


If you only have a weekend to explore the city, staying downtown (or close to it) will be your best option.  Our top picks for lodging include: Sheraton Hotel at Station Square, The Wyndham Grand (near Point State Park), Westin Convention Center, Renaissance Pittsburgh (in the Cultural District) and the historic Omni William Penn.


DAY ONE:  Discover Downtown and The Southside

Explore the City By Foot:  The heart of the city is compact, making it easy to explore by foot. As you make your way down the city streets you will notice how the city has a perfect balance between historical turn-of-the-century and modern architecture.  You will also find that the city has many beautiful public green spaces to sit, relax and enjoy a quick snack.  If you get tired of walking, the city has four downtown “T” stations that provide free transportation within the Downtown and North Shore areas.


What not to miss on your walking tour: UPMC Building (The tallest building in downtown), Allegheny County Court House and Old County Jail on Grant Street, Mellon Square, Consol Energy Center (home of the Pittsburgh Penguins), The First Presbyterian Church (6th Avenue), The Wood Street Galleries, Market Square, The PPG Building and Plaza, The Cultural District — Heinz Hall, Benedum Center (Penn Avenue).

Or, Take A Guided Tour:  If you prefer to learn about Pittsburgh’s rich history before setting out on your own, a take a professionally guided tour through:  Just Ducky Tours (see the city by land and water), Hop On Hop Off Double Decker Bus Tour, Bike The Burg (tour the city by bike).

Grab lunch in Market Square:  Diamond Market Bar & Grill’s outdoor patio is the perfect place to relax and take in the beauty of Market Square.


Visit Point State Park:  Tour Fort Pitt Museum, step inside the past as you enter the Fort Pitt Block House (the oldest building in Pittsburgh) and capture a few snapshots of the fountain.

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Explore the Southside:  Take an evening sightseeing or dinner cruise on the Gateway Clipper.  A unique way to enjoy spectacular views of the city as you cruise along the three rivers.

Have dinner or shop at Station Square:  This historic 52-acre waterfront complex has great views of the city, a variety of restaurants and specialty shops to explore.

Ride the incline to the top of Mount Washington:  One of the most picturesque views of the city.  Best time to visit is right before dusk to watch the city slowly light up the night sky.  Stop in DiFiore’s Ice Cream Delite for a sweet treat as you enjoy a walk along Grandview Avenue.


Late Night Fun: For the traveler looking for nightlife, make your way up to Southside’s Carson Street for an eclectic mix of dining, art and evening entertainment.

DAY TWO:  Northside, The Strip District, Shadyside and Oakland

Tour Heinz Field and/or visit The Carnegie Science Museum (if traveling with kids)


Walk along Allegheny Riverfront Park:  See the Mr. Rodgers statue, the Law Enforcement Memorial, the Veterans War Memorial and the Korean War Memorial.

Visit the Andy Warhol Museum, Mattress Factory (featuring work from artists around the world) and/or tour the National Aviary.

Explore The Strip District:  Have lunch and discover great bargains as you tour this historic area of the city.  Click here to read more about the “Strip”.

Strip District

Take a quick tour of Oakland:  See the Cathedral of Learning on the University of Pittsburgh campus, the Carnegie Library and the Soldiers & Sailors Memorial Hall and Museum.  If you have more time, explore the Carnegie Museum of Art.

Visit Walnut Street in Shadyside:  Enjoy upscale shopping and dining as you stroll along this beautiful street.

Take in a Game:  If you are visiting in the summer, cheer on the Bucs at PNC Park; or, if you’re feeling lucky head on over to the Rivers Casino for some nighttime action.


DAY 3: Have a Day Adventure

This is your day to kick back and enjoy one of three different full or half-day activities:

  • Get your thrills at Kennywood Park in Homestead and enjoy a fun filled day at one of the country’s best amusement parks.
  • The Pittsburgh Zoo and PPG Aquarium (Highland Park) – home to 400 species and 4,000 animals.
  • Visit the Pittsburgh Botanic Gardens in the morning and The Frick Pittsburgh in the afternoon for a day of culture and beauty.


If you have more than a weekend:

  • Take a day trip to Frank Lloyd Wright’s iconic Falling Water (Mill Run, PA)
  • Go white water rafting at Ohiopyle
  • Visit Flight 93 National Memorial honoring the passengers and crew for their courage on 9/11 (Stoystown, PA)

Things that will surprise you about the City of Pittsburgh:

  • The cleanliness of the city: This is a city where you will be hard-pressed to find litter or grittiness that is typically associated with traditional urban downtown areas.  There are numerous public spaces and mini-parks that enhance the cleanliness and beauty of the downtown area.
  • This city’s downtown is compact and can easily be explored on foot.
  • Public transportation is FREE within the downtown and North Shore zones. Not only is the underground light-rail system free, but there is also classical music playing while you wait for the next train.
  • Pittsburgh locals are extremely friendly and will go out of their way to help you.
  • There is so much to see and do, one weekend is not enough.



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