Love Is In The Air

Birds are chirping, bees are buzzing, and love is in the air. Now is the perfect time to plan memorable dates that celebrate the season’s beauty and the city’s romantic offerings. From scenic outdoor spots to cultural experiences and culinary delights, Pittsburgh has something for every couple. 

Dependable Drive-In Theater

Looking for a classic date night with a twist? Head to one of the last local drive-in theaters located just west of the city in Moon Township for a nostalgic evening under the stars. Snuggle up in the comfort of your car, grab some popcorn, and enjoy a double feature of today’s newest showings with your special someone. Dependable Drive-In is always a local favorite, and it is no wonder why when it is literally the perfect way to relive the charm of yesteryear while creating new memories together. 

Bike Ride on the Great Allegheny Passage

Rent bicycles and set off on a scenic ride along the Great Allegheny Passage, a 150-mile rail trail between Pittsburgh, Pennsylvania and Cumberland, Maryland. While you don’t have to traverse the whole thing, you’ll surely be charmed by even the smallest section! This picturesque trail follows the path of an old railroad, winding through lush forests, small towns, and alongside rivers. Come prepared and pack a picnic lunch to enjoy at one of the trailside picnic areas – or stop at a quaint cafe for a romantic al fresco meal.

Visit Randyland

Get whimsical at Randyland, a colorful and eclectic outdoor art installation in Pittsburgh’s North Side. Created by local artist Randy Gilson, this vibrant oasis is filled with quirky sculptures, mosaics, and murals that are sure to spark conversation and ignite your imagination – and the best part of all, it is totally free! Featuring found object art, Randyland is widely regarded as one of America’s most colorful public art landmarks. The outdoor museum has played a pivotal role in breathing life into the artistic and creative soul of the city, attracting visitors from across the nation and around the world. Called an essential part of a perfect day in Pittsburgh by Anthony Bourdain: Parts Unknown, Randyland is certainly a can’t-miss for any couple looking for a fun and unforgettable date. 

Mt. Washington Overlook

For a truly breathtaking experience, head to the Mount Washington overlook, named for a young George Washington who once stood on what is now Grandview Avenue and mapped the land and rivers below. Whether you take the historic Duquesne Incline or drive up Grandview Avenue, you and your partner will be rewarded with panoramic views of the city skyline, especially stunning during and just after sunset. Share a romantic moment as you watch the city lights come to life against the backdrop of the setting sun. Round out your evening with reservations at one of the area’s many fine-dining restaurants that offer even more spectacular views overlooking the city and rivers. 

Concerts at KeyBank Pavilion

While its name might keep changing, one thing never does: the entertainment! You can get back to reveling in the magic of live music under the stars at the KeyBank Pavilion. Located just outside of the city in Burgettstown, Pennsylvania, this outdoor amphitheater hosts an array of concerts and events throughout the spring and summer months. From intimate acoustic performances to blockbuster stadium shows, there is something coming to KeyBank for every music lover to enjoy. Check out the upcoming show lists now to get your tickets ahead of time, then plan to pack a blanket or some chairs and settle in for an unforgettable evening of music and entertainment. 

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