A Weekend in Pittsburgh: Explore Shadyside, Scenic Views, and Adventures

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Pittsburgh is a gem for solo female travelers who love delicious vegetarian eats, quirky shopping spots, and unforgettable outdoor experiences. Whether you’re strolling through the boutique-lined streets of Shadyside, marveling at panoramic views from the city’s iconic inclines, or savoring plant-based meals, Pittsburgh is a city that surprises and delights.

But navigating Pittsburgh’s maze of bridges, multitude of neighborhoods, and winding streets can be tricky—one wrong turn and you’re on a scenic (but time-consuming) detour. I’ve got you covered with everything you need to know to make the most of your weekend. Let’s dig in!


Why Shadyside Should Be Your Home Base

Shadyside, in Pittsburgh’s East End, is a charming neighborhood filled with boutique shops, cozy vegetarian-friendly cafes, and a laid-back vibe. It’s walkable, vibrant, and has just the right mix of charm and convenience for a weekend escape.


Shop, Eat, and Wander in Shadyside

Boutique Bliss: Shop Local Gems

Shadyside is a haven for shopaholics with a taste for the unique. Here’s where to wander:

From retro finds to handmade treasures, Shadyside is where boutique dreams come true!


Savor the Vegetarian Scene in Shadyside

Fuel your weekend with these vegetarian and pescatarian-friendly eateries:

  • The Urban Tap: A gastropub offering creative vegetarian options.
    What to Try: The burrata pesto pasta.
  • Cafe Moulin: A cozy creperie serving up savory and sweet delights.
    What to Try: The Barcelona French Toast—deliciously decadent.
  • Muddy Waters Oyster Bar: New Orleans-inspired dishes 
  • What to Try: Seafood Gumbo.
  • Mercurio’s: A family-run pizzeria known for its Neapolitan pizzas and gelato.
    What to Try: The Margherita pizza and seasonal gelato.


When the Margherita pizza is this perfect, you savor every bite!


Take the Incline for Jaw-Dropping Views

Pittsburgh is known for its breathtaking views, and there’s no better way to see the city than from the top of the Duquesne Incline. This historic cable car takes you up Mount Washington, offering stunning panoramic views of the city and its iconic rivers.

Once you’re at the top, spend some time exploring the overlook or grab a bite at one of the restaurants with a view.

Pro Tip: Ride the incline at sunset for a truly magical experience.

From Mount Washington, Pittsburgh shines even brighter. Sunset views for the win!


Get Active with Steel City Outdoor Adventures

For a little outdoor fun, head to Steel City Outdoor Adventures. They offer rafting, hiking, saling, and urban bike tours tailored to solo travelers and small groups. It’s a perfect way to explore Pittsburgh’s rivers and scenic trails while staying active.

Pro Tip: Book early to snag a spot on popular tours.


Biking through Pittsburgh’s rivers is exhilarating.


Try Walk the Burgh Tour

If you’re new to solo travel and feel hesitant,  Walk the Burgh Tour is an excellent way to navigate Pittsburgh while soaking in its history and culture. Led by locals, it’s a great introduction to the city’s layout, helping you avoid those infamous wrong turns.


Solo travel but never alone! Exploring the Burgh with new friends.


Explore Beyond Shadyside: Cultural and Natural Gems

Phipps Conservatory and Botanical Gardens

Immerse yourself in the beauty of nature with a visit to this lush green oasis. Each season brings new displays, from tropical rainforests to themed flower exhibits.
Pro Tip: Pre-book tickets to avoid waiting in line.


Rain or shine, Phipps Conservatory is a slice of paradise.

The Frick Pittsburgh

This historic estate is a peaceful retreat with art collections, gardens, and a charming cafe.

Three Rivers Heritage Trail

Perfect for walking or biking, this trail offers picturesque views of the rivers and bridges.


Navigating Pittsburgh Without Stress

Here’s the deal: Pittsburgh’s bridges and hills are gorgeous, but they can also be confusing. A wrong turn can take you far from your intended destination, so make your GPS your best friend.

Tips for Easy Navigation:

  • Bookmark key destinations in your GPS.
  • Double-check your route to avoid taking the wrong bridge.
  • When in doubt, stick to major roads and landmarks.


Bridges for days in the Steel City. Trust me, your GPS is a lifesaver!


Plan Your Perfect Pittsburgh Weekend

From Shadyside’s charming boutiques and veggie-friendly eateries to the breathtaking views from the Incline and endless outdoor adventures, Pittsburgh truly has something for everyone. Whether you’re indulging in creamy gelato, hunting for vintage treasures, or paddling along the city’s iconic rivers, a weekend in the Steel City promises unforgettable stories. And that’s just one neighborhood—Pittsburgh’s offerings are as diverse as they are exciting! Simplify your travel by booking a ride with services like GetTransfer to navigate from the airport to your accommodations.

💡 Bonus Tip for Summer Travelers: If you’re in Pittsburgh in late May, don’t miss the Dollar Bank Three Rivers Arts Festival. This multi-day event features incredible live music, art installations, and delicious food vendors. The festival grows bigger every year, so prepare for extra traffic and limited parking.

Three-Rivers-Arts-Festival.

Art, music, and good vibes in the heart of Pittsburgh. Don’t miss the Three Rivers Arts Festival!

💡 Winter Visitors Rejoice: If you’re here between November 29, 2024, and December 31, 2024, make time for Dazzling Nights at the Pittsburgh Botanic Garden in Oakdale. This enchanting holiday event features breathtaking light displays, perfect for a cozy, festive evening.
🔥 Save on Select Nights: Special pricing is available through December 19th, with tickets starting at just $19 for kids and $22 for adults. These discounted spots fill up quickly, so book early and save!


Holiday magic at its finest! Dazzling Nights lights up the winter season.

💡 Pin it for later: Save this guide for your next adventure!

Stay curious, stay hungry, and keep exploring!

-Beth

Hi, I’m Beth! Growing up as a pescatarian in a family of meat lovers, I had to get creative at the dinner table (the family dog was a big fan of my strategy). My love for food, travel, and photography was sparked at home and grew into Bite-Sized Adventures. Join me as we explore the world one bite and snapshot at a time!

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