Date Ideas in Pittsburgh

Date Ideas in Pittsburgh

Dates are all about excitement and electricity. You want to go somewhere that offers a chance to get to know each other better while also giving you lots to discuss. Finding the right destination can help set the tone for not only this date, but the ones that follow.

We’ve compiled this list of date ideas in Pittsburgh that will also fit your budget. You can enjoy these fun activities whether you’re on your first date or celebrating your 25th wedding anniversary.          

Go on a Self-Guided Walking Tour

Even those who’ve lived in Pittsburgh their entire lives don’t know everything about the city. Learn more and spend quality time walking together by downloading one of six self-guided walking tours of downtown offered by the Pittsburgh History & Landmarks Foundation.

Each PDF includes a map of the areas you explore, the starting location, and detailed history of the buildings you find along the way. Plan the tour to end at a restaurant for dinner.

Visit Mt. Washington

In hilly cities, funicular railways were popular means of getting from the top to the bottom of a steep hill. Pittsburgh is home of two working funiculars, a.k.a. inclines. 

For a nominal fee, take the Monongahela or Duquesne inclines, located less than a mile apart, to the top of Mt. Washington and make your way to an observation deck. From this vantage point, you can see gorgeous views of the city, including the rivers and skyscrapers. When you’ve had your fill of scenery, head to Emerald View Park where you can walk one of the trails.

See the Art in Oakland

Pittsburgh is known for beautiful public art installations across the city. Visit the many options in the Oakland neighborhood, home to three of Pittsburgh’s universities as well as several museums, by obtaining a free book with a self-guided walking tour from the Greater Pittsburgh Arts Council. Visit the council’s office on Penn Avenue, get it at the Pittsburgh Welcome Center on Fifth Avenue, or download your copy online.

You can complete the tour in about two hours, leaving you plenty of time for dessert or coffee at one of Oakland’s many eateries.

Listen to Free Music

Pittsburgh has a number of opportunities to catch free music throughout the city.

  • JazzLive: Tuesdays, 5-7 p.m. from June to September at Agnes R. Katz Plaza. Tuesdays, 5-8 p.m. from October to May at Theater Square’s Cabaret and Backstage Bar.
  • Third Thursdays at WYEP: Third Thursday of the month at the WYEP Community Broadcast Center, with doors opening at 6:30 p.m.
  • Pittsburgh Banjo Club: Wednesdays, 8-11 p.m. at the Allegheny Elks Club in North Side.

Get to each venue early, as space is on a first-come, first-served basis. You can eat beforehand or, for JazzLive, bring a picnic dinner to enjoy while you listen to music.

See the Stars at the Allegheny Observatory

For an out-of-this-world date, take a free tour at the University of Pittsburgh’s Allegheny Observatory. Tours begin at 8 p.m. and are held Thursdays in May-August and Fridays in April-October. Remember to make reservations beforehand.

Want even more stars and skies? The observatory hosts public lectures every third Friday of the month. Call in advance for reservations.

Visit the Grounds of the Frick

The Frick Art Museum is a Pittsburgh mainstay, but if you’ve only visited the museum itself, you’re missing out. You can access the museum and historical center grounds, Car and Carriage Museum, and the greenhouses for free. See automobiles from the turn of the 20th century and more.

Go for a Walk Along the Water

Pittsburgh is the convergence spot for the Ohio, Allegheny, and Monongahela rivers. Walking along the rivers provides endless opportunities for sightseeing and taking fun photos. Plus, you’ll eventually come to the city’s two iconic sports stadiums, which offer a great atmosphere on game nights.

Paddle a Kayak

Prefer to see the rivers a bit closer up? Rent a kayak and paddle to your heart’s content. A tandem kayak allows you to work together to paddle. You’ll work up quite an appetite on your kayak ride, so make sure to pick a restaurant located near your rental spot to relax and unwind after all that exercise.

See a Movie in the Park

When the weather is warm, Pittsburgh has a plethora of outdoor activities to keep you busy on date night, and a lot of them are free. Bring a blanket and some refreshments, and enjoy a variety of free movies offered at parks around the area in the spring, summer, and fall.

Take in the Birds at the Aviary

The National Aviary has everything from penguins to flamingoes. Daily events allow you to learn more about our feathered friends, and you can schedule your visit around a feeding or an encounter for a closeup view of the birds.

Pittsburgh provides many fun opportunities for couples. Get outdoors or enjoy one of the many cultural offerings. You’ll treasure your time together, no matter which activity you choose.

For additional money-saving ideas, visit our WalletWorks page.  

Date Nights in Pittsburgh

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