Your Day in Oakland: A 24-Hour Itinerary

This itinerary is designed for a perfect day exploring this iconic Pittsburgh neighborhood. It’s a walkable plan that combines iconic sights, local food, and unique experiences.

Pictured |

Cathedral of Learning

Credit |

Dustin McGrew

MORNING

LUNCH

AFTERNOON

EVENING

DINNER

LATE NIGHT

Morning: Diners & Delicacies

Dive into Diners: Oakland has its fair share of diners and coffee shops that will make sure your day starts right. We recommend Pamela’s Diner on Forbes Avenue, as its colorful interior and retro vibes will make you feel like you stepped right into a 60’s movie. Keep in mind that Pamela’s is a cash-only establishment, which in our opinion, just adds to that old-timey feel.

Just a Cup of Joe: If you’re just feeling like grabbing a cup of coffee, you’ve come to the right neighborhood. Divvy Coffee & Buns is right along the main drag and has unique flavored coffee. La Gourmandine has every pastry you can imagine and delicious cups of coffee to boot. Redhawk Coffee Roasters is a little off the beaten path in a quaint corner of the neighborhood, with excellent coffee and a relaxing ambience

Lunch: Outdoor Dining & Overlooks

Take It Outdoors: Lunch is the perfect time to eat outdoors, so we recommend heading to a place in and around Schenley Park. The Porch is a neighborhood bistro in the heart of vibrant, bustling Oakland. Situated within beautiful Schenley Plaza, this new concept is a come as you are, no reservations restaurant serving the University community, neighborhood regulars and park user alike. Creating simple, delicious, scratch made food that we love to cook and eat; The Porch is an authentic everyday experience for a casual meal, a special occasions destination, or a great place to enjoy the sights and sounds of Oakland while unwinding with a cold drink with new friends or old.

You can also have a light lunch at the Schenley Park Café and Visitor Center, with exposed brick, high ceilings, and a private balcony that overlooks Schenley Park. There’s also a gift shop in the Visitor Center, so you can get something for everyone to commemorate your trip!

Afternoon: Garden Party

Curated Art: Phipps Conservatory and Botanical Gardens, encompassing 15 acres including the historic 14-room glasshouse and 23 distinct gardens, sits in Schenley Park and is one of Pittsburgh’s greatest treasures. Experience breathtaking seasonal flower shows, exclusive commissioned exhibits, immersive Tropical Forest, renowned orchid and bonsai collections, industry-leading sustainable architecture and green practices, delightful butterflies, fun family activities and much more. Discover why Phipps is a top destination for all ages.

All Natural: And for a quick walk through nature in its natural habitat, head out of Phipps and take in Schenley Park itself! Created in 1889 with land donated by heiress Mary Schenley, the park now contains 456 acres of trails, woods, and attractions. Take a ride on the PNC carousel in Schenley Plaza, soak in the sunshine on the Arthur D. Hellman Lawn, relax on Flagstaff Hill, play a round at the Bob O’Connor Golf Course, head to the Schenley Oval Sportsplex for ice skating or summer sports, or take a dip in the swimming pool. And of course, the trails offer a refreshing and convenient escape from city noise and congestion.

Evening: Museum Crawl

Two Museums in One: Oakland is filled with must-visit museums. The Carnegie Museums of Art and Natural History are two museums combined, making it your one-stop shop for the art lover and history lover in your group. The Carnegie Museum of Art, renowned for its collections of more than 100,00 objects, features a range of visual art, including painting, sculpture, decorative arts, design, and photography. Located within the same historic building, The Carnegie Museum of Natural History is home to one of the country’s largest and most celebrated natural history collections featuring 22 million objects and specimens, ranging from real dinosaur fossils and dazzling gems and minerals to iconic wildlife dioramas.

Honor Our Troops: Soldiers and Sailors Memorial Hall & Museum is one of the nation’s only military museum dedicated to honoring the men and women of all branches of service. Within this historic landmark are exhibits displaying artifacts and a concert hall, just to name a few things.

Learn Your History: And while this isn’t technically a museum, we’d be remiss not to mention checking out the Nationality Rooms at the Cathedral of Learning. The Cathedral, affectionately known as “Cathy,” is the tallest academic building in the Western Hemisphere and hosts dozens of rooms that pay homage to the countries around the world. You’ll be immersed in culture from the second you step into the building, but the Nationality Rooms are where it truly shines.

Dinner: File Down Forbes Avenue

Forbes Avenue is one of Oakland’s main drags, which means it’s chalk full of places to stop for a bite. Stop at Stack’d for burgers, CHiKN for chicken sandwiches, Primanti’s for a Pittsburgh staple, The Colombian Spot for Latin, Noodle House for ramen, or CAVA for Mediterranean, just to name a few.

If you’re feeling pizza, we recommend checking out Cork & Crust in The Oaklander Hotel. This new concept has turned the tables on your favorite ‘zas, establishing an elevated wine bar experience to sip and dine as you see fit.

Late Night: College Watering Holes

A Main Stay: Oakland is, at its core, a college neighborhood, which means its bar scene is filled with cheap drinks and good times. Mario’s Oakland Saloon is a staple to Pittsburgh, with a dance floor that runs through the early morning and a kitchen serving up all you need to keep yourself going.

Off the Beaten Path: If you’re looking for more hole-in-the-wall places that are a little off the beaten path, check out Gene’s Place or Bootleggers. Both have that classic dive bar feel (and prices) that will have you wondering if you left the neighborhood entirely.