Embark on a thrilling 4-day city road trip through Pittsburgh’s Downtown, Oakland, Shadyside, Squirrel Hill, and Mount Washington. Uncover the ultimate neighborhood and city guide, revealing top attractions, dining experiences, and hidden gems.
Plus, enjoy the best car rental service from the moment you touch down at the Pittsburgh airport, making getting around easy (well, as easy as navigating Pittsburgh’s renowned unmarked roads can be!). Get ready to explore the exciting Pittsburgh Adventure now!
Welcome To Your Pittsburgh Adventure Yinz
Hello, Yinz, and welcome to Pittsburgh, the Steel City, where your ultimate 4-day city and neighborhood road trip adventure begins. With a hassle-free and luxurious rental car from the airport rental options, you can explore the city at your own pace.
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Seamless Car Rental Experience with Car Rentals at Pittsburgh Airport
When your plane touches down at Pittsburgh International Airport, you’ll be ready to kick-start your city and neighborhood adventure with a seamless car rental experience from whichever rental agency you choose.
As you step off the plane, there’s no need to worry about complicated logistics or lengthy processes. Ensure you have reserved your choice vehicle, and accessing your rental car becomes a breeze.
Make Sure To Rent A Car At The Pittsburgh International Airport
Whether a premium car or a regular car, make sure you have a rental car that will meet your needs and pick it up at the airport so you can navigate like a pro.
When renting a car at Pittsburgh Airport, get a premium car that meets your needs. Their fleets offer economy cars, sedans, SUVs, and luxurious vehicles from brands like BMW.
Who’s ready to start exploring the ‘burgh’ through cultural attractions, yummy food, and stunning views?
Day 1: Airport Arrival and Exploring Downtown Pittsburgh
Pick Up Your Car Rental: Start your road trip adventure by picking up your rental car at the Pittsburgh International Airport. With a wide range of vehicles, including sedans and SUVs, you are sure to travel in style and comfort throughout your trip.
Check into Upscale Downtown Hotels: Once you arrive in downtown Pittsburgh, check into one of the three upscale hotels recommended for a luxurious stay.
- The Omni William Penn Hotel
- Fairmont Pittsburgh
- Kimpton Hotel Monaco Pittsburgh
Each is renowned for its impeccable service and elegant accommodations and offers prime locations in the city’s heart so you can easily take on your Pittsburgh adventure.
Explore the Strip District and Enjoy Lunch: After settling into your hotel, start your Pittsburgh adventure by heading to the vibrant Strip District for a delightful walking tour and Lunch. Indulge in the iconic Primanti Brothers sandwich or try trendy options like Gaucho Parrilla Argentina or Smallman Galley.
Visit Washington’s Landing and Enjoy the View: After Lunch, take a short drive to Washington’s Landing and visit RedFin Blues, a riverside restaurant and bar offering a refreshing view of the city from a different perspective. Relax with a light beverage and soak in the picturesque scenery.
Vintage Shopping and Dining in Lawrenceville: Drive over to Lawrenceville, a trendy neighborhood known for its vintage shops, vibrant arts scene, and bustling dining options. Explore unique stores like Who New? Retro Mod Decor and Decade, then enjoy happy hour at popular bars such as Round Corner Cantina or Spirit. For dinner, savor the culinary delights at restaurants like Morcilla, The Vandal, or Apteka.
Stroll Along Point State Park Fountain: Conclude your Pittsburgh adventure day with a leisurely stroll along Point State Park Fountain, where you can admire the beauty of the park and the confluence of Pittsburgh’s three rivers. Reflect on your day of exploration and immerse yourself in the serene atmosphere.
Day 2 of A Pittsburgh Adventure: Discovering Oakland & Its Attractions
Breakfast at Pamela’s on the Strip: Start your day with a delicious breakfast at Pamela’s Diner on the Strip, known for its iconic crepe-style pancakes, classic breakfast dishes, and super big servings, and that’s a good thing because taking on the Pittsburgh adventure needs fuel.
Visit the Carnegie Museum of Natural History: Immerse yourself in the wonders of natural history with a short visit to the Carnegie Museum of Natural History in Oakland. Marvel at the extensive dinosaur exhibits, explore the Hall of Minerals and Gems and learn about the fascinating ecosystems of the world. Your Pittsburgh adventure inside the Carnegie Museum of Natural History will transport you around the world.
Lunch in Oakland: Treat yourself to a satisfying lunch at The Porch at Schenley or choose from other popular spots like Fuel and Fuddle or Union Grill, known for their diverse menus and cozy ambiance.
Dinner in Oakland: Indulge in a delightful dinner at one of Oakland’s top-rated restaurants as part of your Pittsburgh adventure at any of these restaurants.
- Experience the flavors of global cuisine at Legume
- Enjoy modern American fare at Butterjoint
- Savor authentic Italian dishes at Girasole
Evening Entertainment: After dinner, consider catching a show or performance at one of the cultural institutions in Oakland, such as the Pittsburgh Playhouse or the Petersen Events Center. Immerse yourself in the vibrant arts scene of the neighborhood.
If there is no show of interest, but you are visiting during Spring and Summer, consider a ballgame at PNC Park or, if in the Fall and Winter, a Pens Game!
Day 3: Visiting Shadyside and Squirrel Hill
Today, you’ll be driving, so take your rental and drive a few miles out of the city’s heart into 2 incredible neighbors that must be part of any Pittsburgh adventure. What a fun day you are going to have, it is one of my favorite places, as I attended a local college up in the area and spent many days walking, dining, shopping, and enjoying this unique area.
Breakfast in Squirrel Hill: Start your day in Squirrel Hill, a charming neighborhood known for its eclectic shops and eateries. Enjoy a delicious breakfast at Pigeon Bagels or the Square Cafe. Don’t worry. There is plenty of parking for your car rental; from street parking to garage parking, you will find a spot no worries.
Explore Shopping in Squirrel Hill: Take a leisurely stroll along Murray Avenue in Squirrel Hill, with so many unique shops and boutiques you won’t have enough time to see them all. Browse vintage clothing stores like Avalon Exchange or discover local treasures at Ten Thousand Villages.
Visit the Frick Art Museum: Before heading to Shadyside, drive to and stop at the Frick Art Museum in the neighboring Point Breeze area. Explore the impressive art collection and take a guided tour of Clayton, the historic mansion that belonged to the Frick family.
Lunch in Shadyside: Drive to Shadyside and park conveniently near Walnut Street, the neighborhood’s main shopping and dining district. Enjoy a delightful lunch at popular spots like Noodlehead, Steel Cactus, or Casbah, offering a range of cuisines from Asian fusion to Mediterranean delights.
PRO TIP FOR PARKING: Parking can be very challenging in Shadyside (that’s part of the charm of your Pittsburgh adventure, experiencing the Burgh like a local); we suggest the Shadyside garage and a bit of walking, which you can reward yourself for the extra steps with some Pittsburgh famous treats we are about to share!
Explore Shadyside and Indulge in Sweets: After Lunch, explore the charming streets of Shadyside and visit stores like Moda, Ten Toes, and Kards Unlimited for a unique shopping experience. REWARD those extra steps and stop by Prantl’s Bakery to taste Pittsburgh’s famous Burnt Almond Torte and coffee.
Dinner in Shadyside: As the day winds down, treat yourself to a memorable dinner at top-rated restaurants in Shadyside. Consider dining at Tocayo(we ♥), Paris 66 Bistro, or Umi, known for their exquisite flavors and impeccable service.
Day 4: Mount Washington, Southside & Station Square
Today we will be driving again, so get your rental car and program your navigation system for breakfast at another classic Pittsburgh favorite in the strip!
Breakfast in the Strip District: Begin your day with a hearty breakfast at DeLuca’s Diner in the Strip District, known for its delicious pancakes, omelets, and other breakfast classics. If you get here and it is busy, reprogram your navigation system for Kelly O’s. It’s a few blocks away but enough for you to drive on this Pittsburgh adventure; either place will fill your belly for the morning!
Coffee Break at Il Primo: Grab a cup of coffee at Il Primo Espresso Caffè and enjoy the lively atmosphere of the Strip District before heading to your next destination. I know you might have just had breakfast but this coffee is not to be missed.
Cruise the Rivers and Explore Station Square: Drive to Station Square, where you can park in one of the garages or lots. Embark on a scenic river cruise aboard the Gateway Clipper Fleet and admire the beauty of Pittsburgh from a different perspective.
Gandy Dancer Saloon and the Duquesne Incline: After the river cruise, relax and unwind and wet your whistle (lol) at the Gandy Dancer Saloon, a historic bar with a rustic ambiance. Then, head to the exciting Duquesne Incline, a century-old cable car that will take you to the top of Mount Washington for breathtaking city views.
Splurge on Dinner with a View: Conclude your journey with a memorable dinner at one of the top restaurants offering stunning views. Altius, Monterey Bay Fish Grotto, and LeMont Restaurant are known for their delicious cuisine and panoramic vistas.
FAQs For Your Pittsburgh Adventure
1. What are some top attractions to visit in downtown Pittsburgh?
Downtown Pittsburgh offers a plethora of attractions. Some must-visit places include Point State Park, Andy Warhol Museum, the Heinz History Center, PNC Park for baseball enthusiasts, and Acisure Stadium.
2. How can I explore the cultural attractions in Oakland and Shadyside?
To explore the cultural attractions in Oakland, head to the Carnegie Museums of Art and Natural History, and you’ll want to get your fill of flowers at the Phipps Conservatory and Botanical Gardens and stroll through the University of Pittsburgh campus. In Shadyside, you can visit the Frick Art Museum, shop along Walnut Street, and enjoy the neighborhood’s vibrant dining scene.
3. Are there any scenic viewpoints in Mount Washington?
Absolutely! Mount Washington offers stunning panoramic views of Pittsburgh’s skyline and the three rivers. You can enjoy these views from the observation decks, ride on the Duquesne Incline, and dine on Grandview Avenue in one of the many restaurants with an incredible view.
4. What are some recommended dining options in Pittsburgh?
Pittsburgh has a thriving food scene. Taste the city and neighborhoods of Pittsburgh by visiting the iconic Primanti Brothers for a sandwich, indulge in gourmet cuisine at Altius or Umi, or explore the trendy dining options in Lawrenceville and Shadyside. From international flavors to local specialties, Pittsburgh offers something for every palate.
How Was Your Pittsburgh Adventure?
Congratulations on completing your ultimate 4-day road trip adventure through the captivating city of Pittsburgh! Throughout this journey, you have experienced the thrill of exploring Pittsburgh’s vibrant downtown, uncovering the cultural gems of Oakland and Shadyside, and marveling at the breathtaking views from Mount Washington.
Your rental car has provided you with luxury and convenience, ensuring a memorable and comfortable journey. Pittsburgh has showcased its unique charm, rich history, and culinary delights, leaving you with unforgettable memories. We hope this guide has inspired you to embark on your Pittsburgh adventure and discover the city’s countless wonders.
Unveil the allure of Pittsburgh in a 4-day whirlwind city and neighborhood road trip after flying into the Pittsburgh airport. Explore local hotspots, iconic landmarks, and culinary delights. You’ll love this simple Pittsburgh Adventure.