33 Romantic Date Ideas in Pittsburgh This Season

Summer is in the air in Pittsburgh, which means Yinzers have come out of hibernation to enjoy outdoor patio dining, Pirates baseball, and basking in the glory of the Point Park Fountain. Where summer goes, romance follows, and the Steel City has plenty of opportunities for fun, memorable dates that take advantage of our warmer weather, whether it’s an evening in Kennywood, floating in a Tiki bar on the river, or dining in a treehouse like a couple of highly sophisticated Tarzans. Add these date ideas to your summer bucket list for an enjoyable season with your special someone.

Take a walk around Point State Park

This park where the three rivers meet is perfect for a romantic day outdoors. Pack a picnic and admire the fountain, which is turned on April into October, or go for a hike along the Three Rivers Heritage Trail. The Fort Pitt Museum offers a glimpse into Western Pennsylvania’s history, including the birth of Pittsburgh.

cruisin tikis pittsburgh
Cruisin' Tikis Pittsburgh

Take a Tiki boat cruise

Three Rivers
Grab your date and four friends and relax on a two-hour sightseeing Tiki Cruise on the Three Rivers, being offered for the first time during the summer of 2019. The cruise provides a cooler and bottles of water, and you bring your favorite snacks and beverages. Sounds like a picnic on the water!

Get to know each other in line at Page Dairy Mart

South Side
When the sun’s out, you’d better believe there’ll be a line at this ice cream staple on East Carson Street -- in fact, there’s usually a line even when it’s raining. Waiting in said line is totally worth it for a taste of Page Dairy Mart’s delicious treats, though, and gives you plenty of time to decide what you’re going to get and/or get to know each other, especially if it’s a first date! Once you make it inside, go big and order the Yinzer Sundae (or keep it simple and get a couple of cones to share).

Enjoy cinema by starlight in the city parks

Various locations
Bring your own blanket and prepare to cozy up. This year, free movies offered throughout the city include How To Train Your Dragon: The Hidden World, Bumblebee, Incredibles 2, Mary Poppins Returns, Spider-Man: Into the Spider-Verse, Ralph Breaks The Internet, and Captain Marvel.

bocce ball game
Cat Act Art/Shutterstock

Get 'hot and heavy' with some bocce

Various locations
Pittsburghers don’t like to spend a lot of time indoors when the weather gets nice (mostly because non-rainy/snowy weather is such a rarity to experience). Instead of staying indoors and bowling, get outside with some bocce. To get a grasp of the rules, there are bocce games going on all season long that are perfect for observing or participating (you’ve got to register!), and you could even start your own one-on-one game at a local park.  

Explore Pittsburgh neighborhoods with a public art walking tour

Various locations
Art is everywhere in Pittsburgh, from murals in Garfield to installations in Market Square. Explore all of the art this city as to offer with self-guided tours you and your sweetie can take together or more structured tours with a guide, like taking it to the river with the North Shore Public Art Kayak tour.

sienna mercato
Sienna Mercato

Head to Il Tetto for a fantastic rooftop experience

There are plenty of amazing rooftop experiences in the city -- we’ve got a whole article devoted to them -- but Il Tetto offers one of the most enchanting, with twinkling lights and a beautiful view overlooking Penn Ave. On the off chance it’s raining, don’t worry: The clear, retractable roof can be closed pretty quickly.

Cool down your hot vibes, just for a moment, at Gus and Yia Yia’s

This shaved ice cart has been an institution in the Northside for decades. Pick your flavor, then stroll through the nearby Allegheny Commons park, which features pedestrian bridges, a lake, and a cool view of the Pittsburgh skyline.

Kayak Pittsburgh
Kayak Pittsburgh

Paddle the three rivers with Kayak Pittsburgh

North Shore
During the spring and summer, kayaks are available to rent under the Roberto Clemente Bridge. Opt for a tandem kayak and get your paddles (and your hearts) in sync -- just try to avoid splashing the water in your mouth. 

Indulge in the classics with Bach, Beethoven, and Brunch

Mellon Park
Every summer, Sunday mornings in Mellon Park are accompanied by classical music, from 10:30am till noon. Wake up early, pack yourselves a (booze-free) picnic, and enjoy the free concerts by local orchestras and bands.

Take a moonlit ride at Rolling Hills Ranch

Horseback ride under the stars and get away from city life for a bit. And after you complete the 1.5 hour journey, enjoy a hayride to dinner, which includes barbecue ribs.

escape room pgh
Escape Room Pittsburgh

Get locked up together in an Escape Room

Various locations
In the film Speed, Sandra Bullock’s character said: “Relationships that start under intense circumstances, they never last.” While that statement is debatable, you and your date can play out your own Speed scenario by being locked together in a room for an hour and having to problem-solve your way out of it.

Frame some flirtation at Arsenal Bowl

You can’t strike out when you’re bowling at Arsenal Bowl. Complete with retro vibes and fun themed nights, it’s no wonder Hollywood power couple Emily Blunt and John Krasinski were rumored to be spotted here when they visited Pittsburgh.

The Milk Shake Factory
The Milk Shake Factory

Get old-fashioned at The Milk Shake Factory

South Side
Back in the 1950s, couples would share milkshakes at the local diner. The Milk Shake Factory, located on East Carson Street, allows you to experience that schmaltzy gesture for yourself, complete with classic diner decor and hand-spun milkshakes in delectable flavors like brownie fudge, chocolate raspberry truffle, and peanut butter pretzel.

Test each other’s knowledge at Trivia Night at Franktuary

Every Tuesday, chow down on gourmet hot dogs and poutine while testing your knowledge of pop culture, science, and plenty of other topics. Bonus: Without the use of your phone, you’ll have to focus on each other (and, of course, the trivia).

National Aviary
National Aviary

Set your hearts aflutter at the National Aviary

North Side
Birds of a feather stick together, and couples that go to the Aviary do, too -- and while there are no statistics to back that last fact up, the National Aviary still is a great place for a date. Come for the ‘Burgh’s second most famous penguin named Sidney, and stay for the beyond adorable sloths.

Explore Bicycle Heaven's collection of two-wheelers

This free museum is packed to the gills with bikes of all shapes and sizes -- it even includes the Pee-wee’s Big Adventure bike, prompting immediate humming of “Tequila.” If there is a more impressive collection of bicycles anywhere in the world, we’d like to see it.

Wednesdays are for banjos at Pittsburgh Banjo Club night

North Side
Banjo Night in Pittsburgh is an institution, and something every Pittsburgher should experience once. Every Wednesday (from 8pm-11pm), the Pittsburgh Banjo Club performs at the Elk Lodge in the North Side. Doesn’t sound exciting to you? This short documentary from local videographer Willy James will show you what it’s all about and why it’s not just a fun, free experience for you and your date, but one full of history and culture.

Title Town Soul & Funk Dance Parties
Title Town Soul & Funk Dance Parties

Get your groove on at the Title Town Soul & Funk Party

Spirit gets a little funkier on the first Saturday of each month, thanks to Title Town: a duo of DJs with an enormous vinyl collection. Expect deep cuts from genres like disco, '70s funk, and vintage R&B, all of which should be enough to bring you and your date a bit closer on the dance floor.

Act like a kid while drinking beer at the Carnegie Science Center

North Side
The 21-and-over events at the Science Center are a hot ticket. Who doesn’t love downing a brewski and then sitting in the simulated earthquake cafe? Just remember to bring your ID, and expect a crowd.

Phipps Conservatory and Botanical Gardens
Phipps Conservatory and Botanical Gardens

Explore seasonal shows at Phipps Conservatory

Any season’s the right season to go on a date at Phipps in Oakland. Whether it’s spring flowers or winter lights, strolling through the beautiful greenery here is great for sparking conversation and romance.

Get feline-friendly at Colony Cafe and Wine Bar

Strip District
For animal lovers who aspire to be person-lovers as well, this is about as perfect as it gets. Book a visit to the Cat Loft before heading to the coffee and wine bar area for espresso, wine, cheese, and an assortment of other noshing options.

Butterwood Bake Consortium
Butterwood Bake Consortium

Indulge your sweet tooth at the Butterwood Bake Consortium

This dessert cafe, with its charming baroque decor and romantic mood lighting, serves delicious cakes and pies by the slice. It even offers plenty of vegan options, like chocolate strawberry cake and chocolate pudding, if your date is… y’know, vegan.

Yuk it up at Arcade Comedy Theater

Improv, live sitcoms, and more await at this BYOB spot for funny, with new shows every weekend. Better yet: Take a comedy class with your significant other and chuckle your way toward warmer days. Victor Hugo said, “Laughter is the sun that drives winter from the human face.”


Sneak into Acacia on the South Side

South Side
Blink and you might miss it: this speakeasy-style bar looks boarded up, like something out of the Prohibition era, but inside it bustles with old-fashioned cocktails and classic tuneage.

Dine in a treehouse at Tree Tops Restaurant

When you’re a kid, the ideal hangout is an awesome treehouse. This doesn’t really change when you’re an adult -- only now you can enjoy alcoholic beverages in one. Enter Tree Tops Restaurant, located in Acme, PA, in the Laurel Highlands. It’s deck dining at its finest, as you enjoy gourmet meals and wine amongst the leaves.

Head to Kennywood after hours 

Kennywood is always a magical place, but it becomes especially enchanting after 5pm when dusk starts to set in and the park gets a little less crowded. It’s the perfect setting for some romantic amusement.

gateway clipper fleet
Gateway Clipper Fleet

Take a cruise on the Gateway Clipper

Station Square
For spectacular views of the city, a Gateway Clipper cruise is not to be missed, as it’s a truly romantic and truly Pittsburgh adventure. Choose from dinner cruises, sightseeing cruises, 21-and-over cruises, and more. Just don’t be that jerk who yells “I’m the king of the world,” or you likely won’t get to experience another date here.

Get closer to each other with some salsa dancing

Various locations
Even if you don’t know how to salsa dance, there are plenty of weekly events around the city that include a lesson. On Saturdays, Los Sabrosos Dance Studio in Garfield offers a mini salsa lesson before free dancing (small charge). Visit Salsa Pittsburgh to find a salsa event near you.

Jump around at a trampoline park

Various locations
Trampolining isn’t just for kids; in fact, the activity actually burns 1,000 calories in an hour! Some trampoline parks, like Sky Zone in Canonsburg, are actually tailored for older kids or adults, with Friday Glow! Nights from 9pm-11pm, including a live DJ taking requests.

Play games at Games N’ At

South Side
Duckpin bowling, old-school video games, pinball, air hockey, and pool are just a few of the many games you can challenge each other to at this South Side gem. Think of it as like Chuck E. Cheese for adults: It’s BYOB, and skill games require tokens where you can win prizes at the end.

Or, The Whale
Or, The Whale

Go to Pittsburgh’s most literary restaurant

Book lovers will adore or, The Whale restaurant just for the Moby Dick reference and shipwrecked decor, but in addition to first-rate seafood, it also offers a world-class wine program with a sommelier on staff for enhanced pairing experiences. Match literary witticisms over whites, reds, and more.

Take a cooking class together

South Side
More of a hands-on couple when it comes to food? Gaynor’s School of Cooking offers Couples Night classes with a different menu every month. Learn to prepare a delicious meal together under the guidance of a professional chef and turn one meal into multiples (after all, you can take home the skills you learn!).

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Megan McLachlan is a freelance writer living and working in Pittsburgh. She frequently likes to go on dates with herself around Pittsburgh to places like AMC Theaters and Doce Taqueria.