A great date night is key to staying connected in a relationship. Whether you’re in the early phases of courtship or have been married longer than you can remember, date nights are important to maintaining communication and intimacy. It’s a way to get to know a new love interest or experience a new adventure and make lasting memories. It’s also easy to fall into a dating routine. Whether it’s dining at your usual restaurant or your go-to first-date coffee shop, there are few things worse than a boring date. These Pittsburgh date night ideas are perfect for spicing up your routine!

8 Pittsburgh Date Night Ideas for Unforgettable, Romantic Outings

Kennywood

Kennywood Park is a beloved historic amusement park with plenty of roller coasters and activities for anyone and everyone to enjoy. Experience thrills and adrenaline rushes while tightly holding your date’s hand. Enjoy classic theme park food like ice cream, deep-fried Oreos, or some of Kennywood’s famous Potato Patch fries.

If you’re competitive, challenge each other to a carnival or arcade game, or maybe try to win your sweetheart a special prize. If you’re visiting in the winter, their displays of over two million twinkling Christmas lights add a little extra romance. Just be sure to check their hours beforehand, as they change seasonally!

Arcade Comedy Theater

Arcade Comedy Theatre has been making the people of Pittsburgh laugh for a decade. They offer a full schedule of comedy shows featuring local improv artists, stand-up comedians, and more! Take your date out for a themed game show or a sketch comedy performance that will have you both in stitches.

Arcade Comedy Theatre is also a BYOB venue, so as long as you are over 21, you can bring your own six-pack or bottle of wine (for a small corkage fee.) If you’re feeling brave, you can also enroll in an improv class and try your own hands at comedy! But…maybe start with watching a show first.

PNC Park: Home of the Pirates

PNC Park, home of the Pittsburgh Pirates, is an excellent spot for a date night. Pick up a game during baseball season (who doesn’t love an excuse for a good coordinating date outfit, am I right?) and enjoy everything a great ballpark offers.

Grab a few drinks and some classic ballpark food like hotdogs and popcorn. If you love a Pirates superfan or are looking for a new way to experience PNC Park, you should book a stadium tour! Check out the bullpens, luxury suites, batting cages, and more in this interactive experience.

Cinderlands Warehouse

Cinderlands Warehouse is a brewing facility where dreams - and delicious beers - are made. Peep their impressive production equipment, like towering stainless steel tanks, and sample their classic and creative housemade brews.

With a full menu, a massive kitchen, and a 400 lb smoker, you’ll want to come hungry. Not a beer person? No problem! They also sell signature and classic cocktails to enjoy. There’s also a built-in Bocce court, dome hockey, shuffleboard, and more activities. Check out their weekend brunch menu for a fun daytime date option, too!

Point State Park

Point State Park is a National Historic Landmark in downtown Pittsburgh, located at the meeting point of three rivers. Take in the beautiful city skyline with a stroll or a bike ride, or pack a romantic picnic to enjoy while looking out over the water. Its riverfront location is perfect for an active afternoon of kayaking, fishing, and boating.

Point State Park is also home to the Fort Pitt Museum, highlighting Pittsburgh’s important role in various historic wars and battles. Whatever strikes your fancy, you can find something fun to do and explore with your sweetheart with this Pittsburgh date night idea!

The Milkshake Factory

The Milkshake Factory is one of the best spots in the city to satisfy a sweet tooth. Owned and operated by the fifth generation of chocolatiers, The Milkshake Factory’s milkshakes are made with housemade ice cream and premium ingredients that will make all other milkshakes taste inferior.

Enjoy a classic flavor like chocolate or strawberry, or indulge in one of their signature creations like confetti frosted cupcake and tiramisu. I’d say it’s the perfect opportunity for a romantic two-straws-one-milkshake moment, but let’s be real - you’re not gonna want to share.

Gateway Clipper

The Gateway Clipper fleet offers Pittsburgh sightseeing tours and dining cruises that delight locals and tourists alike. Their Sunset Dinner Cruise is irresistibly romantic. Sail out on the Three Rivers with a drink in hand, taking in the beautiful views with your date.

Enjoy a buffet with delicious hometown dishes, DJ entertainment, and, of course, an incredible sunset. You’ll even get a souvenir picture as you board to keep as a memory of your romantic cruise. Don’t forget to check out their other specialty dining cruises to find one that piques your interest and delights your tastebuds!

Tree Tops Restaurant

TreeTops Restaurant is a dining experience unlike anything you’ve ever experienced before! Enjoy a 3 or 5 Branch (course) dining experience in their main restaurant dining room, surrounded by views of beautiful trees. If you want something a little more intimate, you can dine in their private treehouse-style dining pods.

Their private pods feature 4 - 5 course chef’s menus, meaning your meal is preselected to give you a true culinary experience. It’s a bit of a splurge, and they tend to book up pretty far in advance, so you’ll want to make your reservation sooner rather than later!