Explore Mount Washington

Take a romantic stroll along the iconic Grandview Avenue in Mount Washington, where you can enjoy breathtaking views of the Pittsburgh skyline and three rivers below. Stop by one of the many overlooks to snap some photos or grab a bite to eat at one of the charming restaurants in the area. The Duquesne Incline is also a must-visit for a ride up the mountain in a historic cable car.

Alternative options: Point State Park, PNC Park, Station Square

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Enjoy a Dinner Cruise

Experience a romantic evening on the water with a dinner cruise on the Three Rivers. Enjoy a gourmet meal, live music, and stunning views of the city skyline as you cruise along the rivers. Whether you prefer a luxurious yacht or a more laid-back riverboat, there are plenty of options to choose from for a memorable dining experience.

Alternative options: Gateway Clipper Fleet, Just Ducky Tours, Steel City Cruise

Visit the Symphony

Indulge in a night of classical music with a visit to the Pittsburgh Symphony Orchestra. Treat yourself and your partner to a live performance featuring world-renowned musicians and conductors. Whether you’re a seasoned symphony-goer or a first-timer, the beautiful music and elegant atmosphere are sure to make for a memorable date night.

Alternative options: Heinz Hall, Benedum Center, Byham Theater

Take a Cooking Class

Get hands-on in the kitchen with a cooking class for couples. Learn new culinary skills, create delicious dishes together, and enjoy a fun and interactive date night experience. Whether you’re a seasoned chef or a beginner in the kitchen, a cooking class is a great way to bond with your partner over food.

Alternative options: Chop, Wok & Talk, Gaynor’s School of Cooking, Market District Cooking School

Catch a Show at the Pittsburgh Playhouse

Enjoy a night of theater with a visit to the Pittsburgh Playhouse. Watch a live performance of a classic play, modern musical, or contemporary drama in one of the city’s premier performing arts venues. With talented actors and beautiful sets, a night at the theater is the perfect way to spend quality time with your loved one.

Alternative options: City Theatre, Quantum Theatre, Pittsburgh Public Theater

Paint and Sip Experience

Get creative with your partner at a paint and sip event. Sip on wine or cocktails as you follow along with a local artist to create your own masterpiece. No artistic experience is necessary, making it a fun and relaxing way to bond and unleash your creativity together.

Alternative options: Paint Monkey, Painting with a Twist, Pinspiration

Have a Brewery Tour

If you and your partner enjoy beer, why not go on a brewery tour together? Explore some of Pittsburgh’s best breweries, learn about the brewing process, and sample a variety of craft beers. With vibrant taprooms and knowledgeable guides, a brewery tour is a fun and informative date night activity.

Alternative options: Brew Gentlemen, Dancing Gnome, Arsenal Cider House

Test Your Skills at an Escape Room

Put your teamwork and problem-solving skills to the test with an escape room adventure. Work together to solve puzzles, uncover clues, and escape from a themed room before time runs out. Whether you’re in the mood for a thrilling mystery or a spooky challenge, an escape room is a unique and exciting date night option.

Alternative options: Escape Room PGH, IQ Escape, Breakout Games

Attend a Comedy Show

Laugh your night away with a comedy show at one of Pittsburgh’s comedy clubs. Enjoy stand-up performances from local comedians or big-name acts in a cozy and intimate setting. With plenty of laughs and good vibes, a comedy show is a lighthearted and entertaining date night idea.

Alternative options: Arcade Comedy Theater, Pittsburgh Improv, The Steel City Improv Theater

Visit a Speakeasy Bar

Step back in time with a visit to a hidden speakeasy bar in Pittsburgh. Experience the allure of the Prohibition era with craft cocktails, live music, and an intimate ambiance. Whether you’re looking for a cozy corner to chat or a lively scene to dance, a speakeasy bar is a unique and memorable date night destination.

Alternative options: Butcher and the Rye, Acacia, Maggie’s Farm Rum

Have a fantastic date night in Pittsburgh, PA with these exciting and romantic activities. Remember to book a trusted sitter through Wyndy so you can relax and enjoy your evening out without worrying about the kids. Create lasting memories with your partner and make the most of your time together in the vibrant city of Pittsburgh.