Fun Date Ideas in Pittsburgh For Couples

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Are you looking for ways to spice up your relationship in the Steel City? From romantic dinner spots to exciting outdoor activities, there is no shortage of fun things to do for couples in Pittsburgh.

text reads "Pittsburgh date ideas" with photos of baseball field, skyline, and waterfall.

This is a guest post by Samantha from PA On Pause.

Pittsburgh is a vibrant, cultural city full of unique attractions and possibilities for couples. Here, you can visit iconic landmarks, explore the variety of restaurants and cafes, or spend the day outdoors exploring local parks.

While planning a romantic weekend getaway from Pittsburgh is popular among couples, there are plenty of date ideas to explore without leaving the city.

Whether you and your partner are feeling adventurous or looking for a low-key night out, there are plenty of romantic activities that suit any personality type or interest.

Things To Do In Pittsburgh For Couples

Here are some of the best date ideas in Pittsburgh, from dinner cruises to late-night bars, to help make your next date special!

Explore the Phipps Conservatory at Schenley Park

A Pittsburgh date idea that can be enjoyed no matter the time of day, this could be a great morning stroll with a cup of coffee in hand. Stop by Redhawk Coffee nearby in Oakland for a steaming hot cup to enjoy as you head over to Schenley Park. 

While there are plenty of trails to explore outdoors, make sure you save some time to wander through the beautiful flower gardens inside the Phipps Conservatory. Stop and smell the roses!

Advanced reservations are required, so planning ahead of time for this date idea is best.

Take a Stroll around Point State Park

Point State Park is located in the heart of downtown Pittsburgh, and it’s usually busy with those out for a walk, jog, or just enjoying some green lawn space on a nice day. It’s also a great starting point for a date night in Pittsburgh! 

Make it the whole way out to the point. Here, sit by the fountain to relax and take in the views of the North Shore and stadiums on one side and Mount Washington on the other.

You can also explore the walking trails and learn a little history in the Fort Pitt Museum building. 

After strolling through Point State Park, the two of you surely will be hungry, and Market Square is a great spot nearby to go for a date night dinner.

While there are plenty of dining options, the menu at The Yard includes some delicious gourmet grilled cheese options and juicy burgers.

They certainly elevate the tomato soup and grilled cheese you used to have as a kid!

Head up an Incline for Dinner with a View

skyline view of Pittsburgh, PA.

There are two inclines that will take you from the banks of the Monongahela River up to the top of Mount Washington, the Duquesne and the Monongahela Inclines.

Riding one of these incline rail cars is a very unique Pittsburgh experience, and the views of the city skyline from Mount Washington are some of the best in the city!

After you’ve reached the top of Mount Washington, you’ll want to head to dinner at one of the amazing restaurants with a view.

Make a reservation at Monterey Bay Fish Grotto, and be sure to save room for dessert. The angel food grilled cheese sandwich is as delicious as it is unique.

Mount Washington’s restaurants are quite popular, so walk-in seating can be difficult. Be sure to make a reservation ahead of time so you don’t have to alter your date night plans.

Date Night Ideas In Pittsburgh

Stargaze at the Allegheny Observatory

While it can be difficult to enjoy a traditional stargazing date night in the city, the Allegheny Observatory is a hidden gem where you can enjoy a date night under the stars close to the city lights.

The observatory is located in the center of Riverview Park, just 4 miles north of downtown Pittsburgh, and is managed by the University of Pittsburgh.

There are three viewing domes within the observatory housing telescopes for the best celestial views.

You’ll need to reserve your spots on a tour to gain access to the observatory, as it is still used for active research. The best part, though, is that the tours are free!

Beware that the outdoor temperature will match the temperature inside the viewing domes.

Even during the heat of summer, it can be cool in the evenings, so plan your date attire accordingly.

Cruise the Three Rivers on the Gateway Clipper

The Gateway Clipper Fleet of Pittsburgh offers a wonderful way to cruise the three rivers: Allegheny, Monongahela, and Ohio.

On their riverboat cruises, you will go aboard to experience decades of history, enjoy fun-filled entertainment, and discover all that this great city has to offer! 

Whether you are planning a romantic night out on the water with a dinner cruise or looking for some extra entertainment on a moonlit dance cruise, the Gateway Clipper is sure to deliver.

After cruising the Three Rivers, enjoy the rest of what Station Square has to offer. Stop at the Grand Concourse or Tupelo Honey Southern Kitchen for post-cruise cocktails or dessert.

Enjoy an Evening at the Ballpark

view of Pittsburgh Pirates baseball stadium from home plate seats.

While the Pirates haven’t had much success in the winning department over the last couple of decades, heading to PNC Park for a game is one of the best summertime date ideas in Pittsburgh. 

PNC Park is often recognized among the most beautiful ballparks in the country, and many fans from visiting teams travel to the city just to experience the skyline views from behind home plate. 

Grab a traditional hot dog or opt for a sandwich from the Primanti Brother’s stall inside the stadium.

The best time to plan a ballpark date night in Pittsburgh is when there are post-game festivities, like fireworks over the river or a postgame concert on the field.

Catch Dinner and a Show in the Cultural District

Make a reservation at Gaucho Parrilla Argentina prior to your show. This restaurant is only one block from both the Benedum and the Byam Theatres!

Enjoy traditional Argentine empanadas and high-quality wood-fired meats.

After dinner, enjoy a short walk to your show along the streets of the Cultural District, lined with bright lights and scrolling marquees, just a little smaller in scale than those in larger major cities. 

You can see a traditional broadway production at the Benedum Center or opt for a comedy show at the intimate Arcade Comedy Theater.

After the show, enjoy a late-night cocktail at the Warren Bar and Burrow or Bridges & Bourbon. Both are within easy walking distance, no more than a few blocks from any of the theaters. 

Bring Out Your Inner Child at Kennywood Park

Kennywood Park has been a staple in Pittsburgh for over 100 years, but it is constantly being updated with rides and attractions to keep every visit exciting.

Enjoy a high-speed thrill on the Phantom’s Revenge or take a ride on the creepy indoor coaster called the Exterminator.

Slower-paced and nostalgic rides include the Turtle, Merry-Go-Round, and the leisurely train ride. 

Don’t forget to stop by the Potato Patch for a basket of fresh-cut fries and end the night by winning your date a prize from one of the game booths on your way out of the park.

Take a Road Trip to Ohiopyle

Close up of Ohiopyle Falls.

Get out of the city for the day and enjoy this active date idea from Pittsburgh on a one-hour road trip south of the city.

Explore the southern Pennsylvania countryside and get active on the trails at Ohiopyle State Park. Discover the numerous waterfalls nestled within the park including the massive Ohiopyle Falls and the tall Cucumber Falls.

After the day of hiking and exploring, take a detour back through Farmington and drive past the massive Nemacolin Woodlands Resort. At night, it looks like a magical castle lit up on the hill.

While the resort is quite romantic and could be considered a date weekend getaway destination in its own right, you’re probably not quite dressed for the occasion! 

Instead, head up the road to Braddock’s Inn for a delicious homestyle meal. The chicken and dumplings and country-fried steak are both scrumptious!

There are plenty of unique date ideas in Pittsburgh that will make your night out even more special. With a little bit of planning and creativity, you can find something to wow your partner and have an amazing evening together. 

Whether you take a walk down the city streets or explore one of the many nearby natural attractions, Pittsburgh is a great place for all kinds of dates. 

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

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