Oakland Travel Guide

Discover the best places to visit, things to do, hiking and biking routes, food and drink scene, where to stay, local culture and customs, safety and health, how to get to Oakland, and nearby destinations and excursions in this comprehensive tour guide.


Oakland, located in Pittsburgh Region, Allegheny County, in Pennsylvania, is one of the most vibrant and exciting neighborhoods in Pittsburgh. Known for its historical landmarks, scenic views, outdoor adventures, and a plethora of cultural attractions, Oakland is a must-visit destination in the Mid-Atlantic region. In this comprehensive tour guide, you will discover the best places to visit, things to do, hiking and biking routes, food and drink scene, where to stay, local culture and customs, safety and health, how to get to Oakland, and nearby destinations and excursions.

Introduction to Oakland

Oakland is a diverse neighborhood located in Pittsburgh that is home to many colleges, universities, and cultural institutions. It is a hub for education, arts, and entertainment, with a range of museums, galleries, and theaters. Visitors will find a mix of modern and historical architecture, with landmarks such as Cathedral of Learning, Phipps Conservatory and Botanical Gardens, and Carnegie Museum of Art.

List of Places to Visit in Oakland

Culturally Important Attractions: Museums and Historical Places

Oakland is home to some of the most significant cultural landmarks in the United States. Visitors can choose from an array of museums and historical places, including:

  • Carnegie Museums of Pittsburgh: Composed of four museums, including Carnegie Museum of Art, Carnegie Museum of Natural History, Carnegie Science Center, and The Andy Warhol Museum.
  • Phipps Conservatory and Botanical Gardens: A stunning garden spanning 15 acres and featuring exotic plants and seasonal flower shows.
  • Cathedral of Learning: A historic landmark building on the campus of the University of Pittsburgh, located in the heart of Oakland.
  • Pittsburgh Zoo & PPG Aquarium: A world-renowned zoo with unique species of animals and fishes.

Natural Attractions of Oakland: Outdoor Adventures and Scenic Views

Oakland is also a great destination for outdoor enthusiasts. From scenic views to thrilling adventures, there is always something to do. Some of the must-visit outdoor attractions in Oakland include:

  • Schenley Park: A sprawling park covering 456 acres that offers hiking, golfing, ice-skating, swimming, and other outdoor activities.
  • Panther Hollow Lake: A beautiful lake located in Schenley Park that provides a serene and peaceful environment for relaxation.
  • Phipps Run Trail: A scenic trail through the woods of Schenley Park offering breathtaking views of the surrounding landscape.
  • Forbes Trail: A hiking trail that runs through the heart of Oakland and provides a historical perspective of the area.

Hiking/Biking Routes of Oakland

Oakland is a prime location for hiking and biking enthusiasts. The hills and valleys offer a scenic landscape for bikers and hikers alike. Some of the best hiking and biking routes in Oakland include:

  • Panther Hollow Trail: A scenic trail through the heart of Schenley Park that offers hikers views of the lake and surrounding forest.
  • Three Rivers Heritage Trail: A scenic trail that runs along the banks of the Allegheny River, offering panoramic views of the city skyline.
  • Great Allegheny Passage: A 150-mile trail that runs from Pittsburgh to Cumberland, MD, offering stunning views of the mountains and valleys of western Pennsylvania.

Best Things to Do in Oakland: Activities and Tours

Visitors can choose from a range of activities and tours when visiting Oakland. Some of the best things to do in Oakland include:

  • Visit the Carnegie Museums of Pittsburgh: Explore four world-class museums, including the Carnegie Museum of Art and Carnegie Museum of Natural History.
  • Take a tour of the Nationality Rooms: Located in the Cathedral of Learning, the Nationality Rooms offer a unique glimpse into the cultures and traditions of countries from around the world.
  • Attend a performance at the Pittsburgh Ballet Theatre: The Pittsburgh Ballet Theatre is one of the premier ballet companies in the United States and offers breathtaking performances throughout the year.
  • Explore the historic Oakland Catholic Churches: From St. Paul’s Cathedral to St. Regis Church, Oakland is home to many historic and beautiful churches.

Week-Long Itinerary for Oakland

Visitors to Oakland can make the most of their trip with a week-long itinerary that includes some of the best landmarks and attractions in the area. Here’s a suggested itinerary for a week-long stay:

  • Day 1: Visit the Carnegie Museums of Pittsburgh
  • Day 2: Take a tour of the Nationality Rooms and explore the Cathedral of Learning
  • Day 3: Go hiking in Schenley Park and have a picnic
  • Day 4: Explore the historic Oakland churches and religious sites
  • Day 5: Enjoy a performance at the Pittsburgh Ballet Theatre
  • Day 6: Have a day trip to Phipps Conservatory and Botanical Gardens
  • Day 7: Last-minute shopping in Oakland’s unique shops and boutiques

Food and Drink Scene of Oakland

Oakland has a diverse food and drink scene with many restaurants, cafes, and bars. Visitors can try a range of local dishes and drinks.

Must-Try Dishes

  • Pierogies: A traditional Polish dish consisting of boiled dumplings filled with potatoes, cheese, and onions.
  • Pittsburgh-style Sandwiches: Primanti Brothers is a popular establishment that serves up sandwiches with coleslaw and fries on the inside.
  • Chipped Ham: A thin-sliced ham that is popular in the Pittsburgh region and often served with mustard.

Local Beverages

  • Iron City Beer: A local beer that has gained a cult-like following in the Pittsburgh region.
  • Wigle Whiskey: A local distillery that produces a range of whiskies, gin, and rum.

Where to Stay in Oakland: Hotels, Hostels, and Guesthouses

Oakland has a range of options for travelers looking for accommodations. Visitors can choose from hotels, hostels, and guesthouses, depending on their budget and preferences.

Some of the best hotels in Oakland include:

  • Wyndham Pittsburgh University Center: A hotel located in the heart of Oakland and offering picturesque views of the city skyline.
  • Residence Inn Pittsburgh Oakland/University Place: A hotel located in the heart of Oakland and offering spacious rooms and complimentary breakfast.

What to Buy in Oakland: Souvenirs and Local Products to Bring Home

Oakland has a range of unique souvenirs that visitors can take home to remember their trip. From local produce to handmade crafts, there is something for everyone. Some of the best local products to buy in Oakland include:

  • Pittsburgh-themed souvenirs: Visitors can find a range of souvenirs that celebrate the Pittsburgh culture, including shirts, hats, and magnets.
  • Handmade crafts and arts: Visitors can explore the local arts and crafts scene and take home a unique handmade or painted item.
  • Local produce: Visitors can visit the farmers’ markets in Oakland and take home fresh fruits, vegetables, and other farm-fresh products.

Local Culture and Customs of Oakland

Oakland is a melting pot of different cultures and traditions. Visitors can learn about the unique culture and customs of the area by attending local events and festivals, such as the Pittonkatonk festival and the Three Rivers Arts Festival.

Best Time to Visit Oakland

The best time to visit Oakland is in the spring or fall. The weather is mild, and the foliage is beautiful. Visitors can also enjoy outdoor activities like hiking and biking during these seasons.

Do’s and Don’ts of Oakland

Do:

  • Visit the Carnegie Museums of Pittsburgh.
  • Try the local delicacies, including Pittsburgh-style sandwiches and chipped ham.
  • Attend a performance at the Pittsburgh Ballet Theatre.

Don’t:

  • Leave without exploring the outdoors, including Schenley Park and Panther Hollow Lake.
  • Forget to pack comfortable walking shoes, as many of the attractions require walking and hiking.
  • Miss out on the local events and festivals, such as the Pittonkatonk festival and the Three Rivers Arts Festival.

Safety and Health

Safety in Oakland

Oakland is generally a safe neighborhood to visit, but visitors should take precautions. When out, visitors should avoid walking alone at night and keep valuables out of sight. Visitors should also be aware of their surroundings and stay alert.

Health in Oakland

The medical facilities in Oakland are excellent, thanks to the many hospitals and clinics in the area. Visitors should also be aware of the risk of Lyme disease when hiking in the wooded areas of Schenley Park.

Getting to Oakland: Transportation Options and Logistics

Oakland is easily accessible by both public and private transportation. Some of the transportation options available include:

Airports Near Oakland

  • Pittsburgh International Airport (PIT)
  • Allegheny County Airport (AGC)

Bus Stations Near Oakland

  • Pittsburgh Greyhound Station
  • Megabus Pittsburgh stop

Other Options

  • Uber/Lyft: Ride-sharing services are widely available in Pittsburgh, including in Oakland.
  • Taxis: Taxis are readily available in Oakland and can be reserved in advance.

How to Get Around in Oakland

Oakland is a walkable neighborhood, but visitors can also use public transportation to get around. The best way to explore Oakland is by walking, biking, or using the Port Authority of Allegheny County bus system.

Where to Go Next from Oakland: Nearby Destinations and Excursions

Visitors to Oakland can also explore nearby destinations and attractions. Some of the best nearby destinations and excursions from Oakland include:

  • Visit the Andy Warhol Museum in Pittsburgh.
  • Explore the historic sites of Gettysburg National Military Park.
  • Enjoy a day trip to Ohiopyle State Park and its famous waterfall.

Conclusion

Oakland is a neighborhood with a rich history, vibrant culture, and outdoor adventures. Visitors to the area can enjoy a range of activities, from exploring museums and historical sites to hiking and biking through the hills and valleys. With this comprehensive tour guide, visitors can make the most of their trip to Oakland and discover all the best landmarks, attractions, food, and drink that the area has to offer.

The University of Pittsburgh's Cathedral of Learning The University of Pittsburgh's Cathedral of Learning Map of the Oakland area Map of the Oakland area Map of Oakland Map of Oakland Frick Park Entrance Frick Park Entrance Phipps Conservatory in Schenley Park is an impressive Victorian botanical garden Phipps Conservatory in Schenley Park is an impressive Victorian botanical garden Carved doors in the Hall of Architecture, Carnegie Museum of Art Carved doors in the Hall of Architecture, Carnegie Museum of Art The half-acre, 52-foot-tall Gothic Commons Room of the Cathedral of Learning is surrounded by 29 unique Nationality Rooms on the 1st and 3rd floors that are a must to explore. The half-acre, 52-foot-tall Gothic Commons Room of the Cathedral of Learning is surrounded by 29 unique Nationality Rooms on the 1st and 3rd floors that are a must to explore. Heinz Chapel sits immediately to the east of the Cathedral of Learning and provides free docent led tours. Its stained windows, by noted artist Charles Connick, are some of the largest and most spectacular in the world. Heinz Chapel sits immediately to the east of the Cathedral of Learning and provides free docent led tours. Its stained windows, by noted artist Charles Connick, are some of the largest and most spectacular in the world. Home Plate from Forbes Field's final game in Posvar Hall Home Plate from Forbes Field's final game in Posvar Hall The Nicholas Lochoff cloister in the Frick Fine Arts Building contains some of the best reproductions ever created of classical works of art. The building also contains Pitt's University Art Gallery which is free to the public. The Nicholas Lochoff cloister in the Frick Fine Arts Building contains some of the best reproductions ever created of classical works of art. The building also contains Pitt's University Art Gallery which is free to the public. Hammerschlag Hall, Carnegie Mellon Hammerschlag Hall, Carnegie Mellon Many of Pitt Stage's theater performances occur in the gothic revival Stephen Foster Memorial's Charity Randall Theatre, just one of many performance and theater spaces in Oakland Many of Pitt Stage's theater performances occur in the gothic revival Stephen Foster Memorial's Charity Randall Theatre, just one of many performance and theater spaces in Oakland Pittsburgh Vintage Grand Prix in Schenley Park Pittsburgh Vintage Grand Prix in Schenley Park Looking towards the Pitt campus from the Forbes Avenue business district Looking towards the Pitt campus from the Forbes Avenue business district Walnut Street in Shadyside Walnut Street in Shadyside The The "O", as it is known to local students, is one of Oakland's oldest and most famous student eateries. It has received national publicity for its hot dogs but is well known locally for its greasy food, cheap pizza, extremely large portions in each order of french fries. For decades, the neon on its facade has broadcast its location adjacent to the Pitt campus. Walking a few blocks down Atwood St from Forbes will get you to Oakland's only hookah bar, the Sphinx Cafe, which is located in a former church and is across the corner from the original Mad Mex, famous for their margaritas, which has now expanded into other cities. Walking a few blocks down Atwood St from Forbes will get you to Oakland's only hookah bar, the Sphinx Cafe, which is located in a former church and is across the corner from the original Mad Mex, famous for their margaritas, which has now expanded into other cities. Garage Door Saloon at 223 Atwood St. Garage Door Saloon at 223 Atwood St.