Home Culture A Road Trip Guide to Pittsburgh, Pennsylvania

A Road Trip Guide to Pittsburgh, Pennsylvania

by Taylor Duncan
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Pennsylvania is a huge state with unique cities and smaller towns dotted throughout. If you’ve grown up on the east coast, chances are you’ve been able to visit Philadelphia, in eastern PA, on more than one occasion. But for many, the western part of PA is still a mystery. Enter Pittsburgh, also known as the “Steel City” – an area that has transformed itself into a place of community, high-tech industries, vibrancy, and one of the most walkable places around.  

Pittsburgh, also known as the “Steel City”, has been named one of the Top 100 Best Places To Live in 2020, coming in at number 51 {Jersey City was ranked 56th on the list}.

While you can never go wrong with a baseball game at PNC Park, a Steelers game at Heinz Field, or a hockey game at PPG Paints Arena. There is so much that the ‘Burgh has to offer to its weekend visitors. With endless neighborhoods to explore and a variety of culture and history — your time in this Western Pennsylvania city will be nothing short of extraordinary. So here is your ultimate guide to Pittsburgh, Pennsylvania for your next road trip:

How to Get There

By Car

The distance between Pittsburgh and the NYC area is about 330 miles. If you’re looking for a fun road trip, the journey to Pittsburgh is an easy one. With ample rest stops and open roads – take I-78 W to 1-81 S to 1-76 W, and you’ll be there in no time.

By Bus

There are direct buses departing from New York to Pittsburgh. Services depart more than twice a day and operate every day. The travel time is approximately six hours and 30 minutes by bus. Check with Megabus or Greyhound, as they usually have the most roundtrip options – sometimes as little as $20 for a ticket.

Where to Stay

Kimpton Hotel Monaco Pittsburgh {620 William Penn Place}

Kimpton Hotel Monaco pittsburgh

{Photo credit: @monacopgh}

Located in a 1903 building right in downtown Pittsburgh, the Kimpton Hotel Monaco Pittsburgh is your ultimate boutique hotel. Everything from the stunning room design to the city skyline views – Oh, and two Pittsburgh hot spots are located inside {The Commoner and Hotel Monaco’s outdoor Biergarten}.

Fairmont Pittsburgh {510 Market Street}

Fairmont Pittsburgh

{Photo credit: @fairmonthotels}

Also located in downtown Pittsburgh, the Fairmont is within walking distance to the city’s Cultural District, Market Square, and more. With two restaurants, a full-service spa, and two bars/lounges – you’re sure to have a relaxing stay in the ‘Burgh.

Read More: A Guide to Exploring Princeton

Things to Do

Duquesne Incline {1197 W Carson Street}

Pronounced “doo-KANE” {you’re welcome Duquesne University students}, the Duquesne incline has red cars visible from many areas of the city. Take a ride on one, and up the 100+-year-old incline to see a spectacular, panorama view of the entire city. At the top of the incline, you will find yourself in Mount Washington {see below}.

Market Square 

Market Square 

In the center of Downtown Pittsburgh is Market Square — surrounded by shops and restaurants, this space {a favorite of both visitors and locals} boasts year-round activities. A few restaurants to check out are Primanti Bros. {a legendary Pittsburgh spot, which has been around since 1933}, Pizzaiolo Primo {serving delicious Italian food}, and for craft beer — City Works Eatery & Pour House has over 90 selections on tap.

During the holidays in Market Square, there are festive markets for shopping. And if you visit during the rest of the year, there are a variety of pop-up events — a little something for everyone.

Mount Washington 

Mount Washington

Back in 2013, USA Today named the nighttime view from Mount Washington the second most beautiful place in America, on their list of top ten. Grandview Avenue contains a few fine dining options, and while the food is delicious — the view will blow you away. Altius, Monterey Bay Fish Grotto, and LeMont are all dining options that provide stunning views of Pittsburgh. While La Tavola is the place to go for some authentic Italian food {see below for more on these dining options}.

Warhol Museum {117 Sandusky Street}

Warhol Museum

{Photo credit: @thewarholmuseum}

While he’s very well-known in our tri-state area, Andy Warhol was from Pittsburgh. This museum {located in the North Shore neighborhood} marks the largest collection of Warhol’s artworks and an archive that is a must-see when visiting Pittsburgh.

Point State Park {601 Commonwealth Place}

Providing a beautiful 36-acre destination in downtown Pittsburgh — Point State Park is paved with riverfront trails and epic views of different parts of the Steel City. This park is also home to one of the country’s largest fountains, where the Allegheny and Monongahela rivers meet to form the Ohio River — also known as “The Point”.

South Side

This neighborhood of Pittsburgh boasts culture and community with a variety of boutiques, restaurants, art galleries, theaters, and even a live music venue {looking at you Rex – a fixture on Pittsburgh’s Southside for over a century}. Similar to Hoboken, this area has one of the highest concentrations of bars in any place in the country. So there is plenty to do, especially when it comes to happy hours or celebrating whatever Pittsburgh team is in season.

Strip District

Formerly occupied by warehouses and railroads, “The Strip” is authentically Pittsburgh. This shopping district is your hub for produce stands, sidewalk apparel vendors {if you want to pick up any Steelers gear}, and a bunch of restaurants with a local, lively vibe.


A beautiful, walkable area just outside of the city. Shadyside is known for its mix of upscale boutiques, vintage, antiques, and home decor stores. If you’re looking for some craft beer spots, American eateries, or brunch spots – this is your neighborhood. And on the way in you’ll pass some of Pittsburgh’s most stunning homes, everything from Victorian mansions to fun, modern apartments.

See More: How to Spend a Day in Morristown

Food and Drink

Altius {1230 Grandview Avenue}


{Photo credit: @altius_pgh}

Craft cocktails and city views. Nothing beats Altius when it comes to an amazing dining experience. The restaurant in Mount Washington serves delicious upscale American dishes and will have you dreaming about returning for the stellar #eats and #views.

Coop De Ville {2305 Smallman Street}

Coop De Ville

{Photo credit: @coopdevillepgh}

New to the scene {but has immediately made a name for itself} is Coop De Ville. Expect some mouthwatering Southern-style dishes – and a champagne vending machine {no, you aren’t dreaming}. The best part about it? You get to relive your childhood with arcade games, duckpin bowling, ping-pong, pinball, pool tables, and more. This space is definitely a must-visit.

Sienna Mercato {942 Penn Avenue}

Sienna Mercato

{Photo credit: @siennamercato}

If you’re looking for a rooftop experience while in the Steel City, Sienna Mercato is your go-to. The two-story Italian eatery offers a diverse menu {both food and drinks}. And the rooftop is heated, so have no fear visiting in the winter months. Just prepare to be blown away by the beauty of the city once at the top.

Primanti Brothers {multiple locations}

{Photo credit: @primantibros}

When it comes to Pittsburgh, there is nothing more famous than this sandwich joint. It’s iconic, and often the only thing people really know about the city. Imagine this: a tasty sandwich topped with french fries and coleslaw on heavy Italian bread. Something you probably won’t see anywhere else but the ‘Burgh. 

The Urban Tap {1209 E Carson Street, 216 S Highland Avenue}

The Urban Tap

{Photo credit: @theurbantap}

With locations in both South Side and Shadyside, you’ll have a completely unique experience at The Urban Tap. From creative American dishes to mimosa flights {Yes, we said mimosa flights!} – this gastropub is a favorite among Pittsburgh residents and regulars.

La Tavola {1 Boggs Avenue}

Let’s face it, you’re probably visiting from New Jersey. Therefore, if you’re craving some authentic Italian food – make sure to check out La Tavola in Mount Washington. A long-running, family-owned BYOB – the eatery has some amazing pizza, pasta, and specialty desserts. This spot is tucked back in the neighborhood, so make sure to take your pic with the Mount Washington view before or after dinner!

Mario’s Saloon {1514 East Carson Street, 5442 Walnut Street, 116 Oakland Avenue}

The ultimate neighborhood pub and a Southside stapled. Enjoy trivia, karaoke, or your favorite sports team at Mario’s. With locations in the Southside, Shadyside, and the neighborhood of Oakland – Mario’s boasts a fun happy hour menu and even a shot wheel.

Local Bar + Kitchen {1515 E Carson Street}

Local Bar + Kitchen

{Photo credit: Local Bar + Kitchen}

For a true taste of the ‘Burgh {and western PA in general} – head to Local Bar + Kitchen in the Southside. This spot is known for serving up local brews and some Pittsburgh-favorite foods. Bonus: Local also has a heated rooftop for visitors in the winter.

Jack’s Bar {1117 E Carson Street}

The local watering hole is true Pittsburgh. At Jack’s the beer is cheap, and they start at 7AM. That’s right, 7AM. Open most days that early, and 365 days a year – this spot is a true Southside staple.

It’s impossible to include all of the stunning sights, delicious dining options, and lively activities that happen in Pittsburgh. But hopefully, this will get you started on your journey. Make sure to tag @thehobokengirl in your adventures to the Steel City!


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