25 Places to See, Shop, and Sip in Pittsburgh, Pennsylvania

Museums, Gardens, Parks, Vintage Clothing, Bars, and MORE!

Last Updated on March 12, 2023
25 places to see, shop, and sip in pittsburgh, pennsylvania - It_s Bree and Ben

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You may not know much about Pittsburgh other than its popular nicknames: the “Steel City”, the “City of Bridges,” or the “City of Champions.” But there’s so much more to this East Coast gem than just touring its former industrial centers, admiring its 446 bridges, and trying fries on your salad.

Pittsburgh has a thriving arts community, hundreds of acres of space for hiking, dozens of opportunities to shop small, and a myriad of opportunities to drink big.

Pittsburgh is a wonderful year-round affordable destination, but our recommendation is to visit in the fall so you will be enveloped by fall foliage along every street and hiking trail. With over 90 neighborhoods to explore and exciting events happening year-round, here are the best things to do in Pittsburgh.

A panoramic view of the Pittsburgh skyline from the Duquesne Incline
A view of the Pittsburgh skyline from the Duquesne Incline

Things to Do in Pittsburgh, Pennsylvania

Arts and Culture in Pittsburgh

  • The Andy Warhol Museum: This museum is one of the largest single-artist museums in the world, as well as the largest in North America. See the largest collection of Warhol’s works, which includes over 4,000 videotapes, 300 films, and his pop art paintings.
  • Mattress Factory Museum: Immerse yourself in this modern art museum that fills entire rooms with massive installations, videos, and performance art by local artists.
  • Randyland: Visit this beautiful outdoor gallery created by Randy Gilson to experience an afternoon in a cheerful and colorful space with dozens of murals, objects, and backgrounds. Plan a short photo shoot for you and your friends or simply enjoy the awe-inspiring art
  • Carnegie Museum of Natural History: Learn about dinosaurs, minerals, gems, Ancient Egypt, and more in a collection of over 20 exhibits.
  • Carnegie Museum of Art: Wander through the halls to see over 32,000 objects of a variety of mediums, including film, photographs, paintings, sculptures and 70,000 negatives by Charles “Teenie” Harris
  • Carnegie Music Hall: See a classical music performance in this historic performance venue adorned with marble and red velvet seating. Built in 1895, this is one of Pittsburgh’s most beautiful venues often used for weddings, classical events, and even comedy shows. 
  • Carnegie Library – Main (Oakland): This location serves as the headquarters for Pittsburgh’s historic materials and information about state residents all the way back to 1895. You can also explore their vast collection of graphic novels, literature, government documents, patents, maps, journals, and so much more.
  • The Frick: Learn about the Frick family by touring their property, which includes a restored mansion, a collection of cars and carriages, a currently working greenhouse, and an on-site art museum.
  • Heinz History Museum: While this may sound like a museum dedicated solely to the Heinz company, this museum also has exhibits about Pittsburgh’s historical figures, artifacts from Mister Roger’s Neighborhood, and other seasonal exhibits. 
  • Inventionland: Tour a one-of-a-kind fantasy-inspired work environment where creatives and engineers work in castles, dog houses, speedways, and more!
  • Heinz Memorial Chapel: Built during the Great Depression, this neo-Gothic style chapel was completed in 1938 and was designed by the same architect who designed the Cathedral of Learning across the lawn, Charles Z. Klauder.
  • Cathedral of Learning: This skyscraper was commissioned in the 1920s and became an unconventional community project. Local industries donated steel, plumbing, and other elements to this building, while the people in Pittsburgh were encouraged to donate cents and “buy a brick” for the Cathedral. Like the chapel across the way, it’s in the neo-Gothic style. The Commons Room on the ground floor is four stories high and you can head to the 35th floor to get a gorgeous view of Pittsburgh. Fun fact, it’s the second-tallest educational building in the world!
Brianne Nemiroff and Benjamin Hagerty of It's Bree and Ben posing in front of the Cathedral of Learning
Cathedral of Learning
Cathedral of Learning
Cathedral of Learning
25 Places to See, Shop, and Sip in Pittsburgh, Pennsylvania - It's Bree and Ben
Heinz Memorial Chapel

Outdoor Activities in Pittsburgh

  • Frick Park: Hike through Pittsburgh’s largest regional park, 644 acres, and explore one of their many hiking trails as a break from city life. If you visit during the fall, you will be surrounded by beautiful fall foliage in the most vibrant natural shades you can imagine of orange, yellow, and red.
  • Point State Park: Enjoy views of Downtown Pittsburgh, North Shore, and South Shore while you hike to the convergence of the Allegheny and Monongahela River.
  • Market Square Farmers Market: Buy local goods from some of Pittsburgh’s farmers and craftsmen in the center of Downtown Pittsburgh.
  • Phipps Conservatory and Botanical Gardens: This public garden has been a staple in Pittsburgh’s community for over 125 years. Enjoy this historic landmark that encompasses 15 acres, including a 14-room glasshouse, 23 distinct gardens, and seasonal exhibits.
  • Duquesne Incline: For the ultimate Pittsburgh souvenir, grab a photo with your party on the observation deck and enjoy an incredible panoramic view of Pittsburgh and its skyline. You can also learn more about the Duquesne Incline inside the upper station at its museum and take a ride up and down the century-old cable car!
A view of the Pittsburgh skyline from the Duquesne Incline
A view of the Pittsburgh skyline from the Duquesne Incline
A view of the Pittsburgh skyline from the Duquesne Incline
A view of the Pittsburgh skyline from the Duquesne Incline
Benjamin Hagerty and Brianne Nemiroff of It's Bree and Ben at Frick Park with fall foliage
Fall foliage at Frick Park
Fall foliage at Frick Park
Fall foliage at Frick Park
fall foliage in Pittsburgh
Fall foliage in Pittsburgh

Shopping Small Destinations in Pittsburgh

  • South Side: Give yourself an afternoon to explore the funky vintage shops along Carson Street (especially Three Rivers Vintage and Highway Robbery Vintage), grab a coffee at Beehive Coffee House, and exploring the racks and menu at The Zenith, half antique/half vegetarian restaurant
  • Strip District: This district used to be an industrial neighborhood which transitioned to a space for grocers and wholesalers. Now, it’s a neighborhood of specialty grocery stores, small retailers, and restaurants. Here you can find one of our favorite coffee shops Allegheny Coffee & Tea Exchange, where you can buy coffee beans and tea in bulk from all over the world.
  • North Oakland: After exploring the Carnegie Museum of Art, Natural History, and Music Hall, head north along Craig Street to get lost in used and rare book store, Caliban Book Shop, shop comic books at Phantom of the Attic Comics, or sift through vinyl records at Desolation Row CD’s.
  • Shadyside: This neighborhood has a few small shopping streets for you to peruse at your leisure. Along Walnut Street, you can search through two floors of toys at SW Randall Toyes and Giftes shop (Pittsburgh’s oldest toy shop) or immerse yourself in a stack of books, stationery, or gifts at Kards Unlimited. Along Ellsworth Avenue, vintage fashion lovers can visit two wonderful vintage boutiques: Hey Betty for vintage women’s clothing and accessories, and Eons Fashion Antique for a thoughtfully curated selection of vintage clothes for men and women, arranged underneath walls adorned by Broadway playbills.
Brianne Nemiroff of It's Bree and Ben posing in front of street art in Pittsburgh
Street art in the South Side
Benjamin Hagery of It's Bree and Ben choosing coffee at Allegheny Coffee & Tea Exchange
Allegheny Coffee & Tea Exchange
racks inside of Three Rivers Vintage
Three Rivers Vintage
racks of clothes and hat boxes inside of Eons Fashion Antique
Eons Fashion Antique
racks inside of Three Rivers Vintage
Three Rivers Vintage

Fun Places to Get a Drink in Pittsburgh, Morning or Evening

  • Commonplace Coffee: This beloved local coffee shop chain has six locations around Pittsburgh and is a favorite among locals, students, and tourists alike. Commonplace Coffee roasts their own coffee and makes some syrups in house.
  • The Church Brew Works: If you’ve ever wanted to drink in a church, well now you have your chance! Enjoy local brews while sitting under stained glass windows and magnificent archways and re”pint” about all of your sins.
  • The Abbey on Butler Street: This unique foodie destination is a hybrid coffee house, brewpub, and bistro. Come in for your morning coffee, a place to work in the afternoon, happy hour after work, or a drink with friends late at night.
  • Independent Brewing Company: Come here to try a curated selection of beer made in Western Pennsylvania or expand your horizons beyond the U.S. with a few of their favorite beers from around the world.
  • Hidden Harbor: Who knew everyone would love a Tiki Bar in the middle of Squirrel Hill, but it has become one of the city’s most beloved bars and is a fan favorite amongst press across the country. Get a tropical drink to sip alone or get a larger cocktail to share with your party.
  • Biddle’s Escape: This coffee and tea shop has an extensive menu that will keep you coming back for more. Sit back in their colorful space with a drink of your choice and admire the artwork in the nearby yards.
the inside of the church brew works
The Church Brew Works
the inside of Biddle's Esscape pittsburgh
Biddle’s Escape

Do you need help putting it all together? Here’s a sample three-day itinerary.

Day 1

  • Breakfast: B52 Cafe
  • Morning Activity: Strip District
  • Lunch: Franktuary
  • Afternoon Activity: Shadyside small shopping
  • Dinner: Pizzoli’s Pizza, Pasta, and Paisans
  • Evening Activity: Independent Brewing Company or Hidden Harbor for drinks

Day 2

  • Breakfast: Square Cafe 
  • Morning Activity: Frick Park and Biddle’s Escape
  • Lunch: Allegro Hearth Bakery
  • Afternoon Activity: North Oakland shopping and choose a Carnegie museum or library
  • Dinner: Apteka 
  • Evening Activity: The Church Brew Works or The Abbey on Butler Street for drinks 

Day 3

  • Breakfast: Onion Maiden (brunch) 
  • Morning Activity: Duquesne Incline and South Side shopping
  • Lunch: The Zenith and Commonplace Coffee – MWS
  • Afternoon Activity: Randyland and Mattress Factory Museum or The Andy Warhol Museum
  • Dinner: El Burro
  • Evening Activity: Catch a sports event or live show at Heinz Hall for the Performing Arts or Carnegie Music Hall

We hope you enjoy Pittsburgh as much as we do! To learn more about the vegan restaurants we incorporated into your itinerary, click here to read Top 6 Vegan Restaurants in Pittsburgh, Pennsylvania.

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Our names are Benjamin Hagerty and Brianne Nemiroff. We’re a married couple originally from California. Since we became a couple in 2009, we have always been passionate about travel, both locally and abroad. We were inspired to take a long-term trip in 2017 to explore more of Canada and the U.S. and we soon realized that this wasn’t just a lengthy trip, but a new lifestyle choice, and that we were destined to explore.


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