Date Night in Pittsburgh or Cleveland


Photo by David Dabney

Outfit details: Bodysuit / Skirt / Shoes / Scarf / Coat / Purse

I was born and raised in Cleveland and live and work in Pittsburgh. I’ve been made well aware of the sports rivalry whenever I tell people this piece of information. I’m still convinced that both cities are awesome, which is why I’m sharing date nights you can enjoy in either city. They are only 2.5 hours apart, so if you live in Pittsburgh and have never been to Cleveland or vice versa, get in your car! Either city would be a great road trip for Valentine’s Day or a Galentine’s Day weekend. Here are some restaurants and activities we enjoy in both cities.


East 4th Street & Lola

East 4th street is in the heart of Downtown Cleveland. It’s only open to pedestrian traffic, so you can easily bar or restaurant hop down this charming slice of street. See a comedy show at Hilarities or a band at the House of Blues. Then walk over to Lola Bistro, a Michael Symon original. It offers inventive upscale American cuisine and the perfect date night vibe. Finish your night with a chocolate martini and dessert at the Chocolate Bar. I highly recommend the Molten Lava Cake.

Cleveland Museum of Art & Little Italy

This has to be one of my favorite date nights. The Cleveland Museum of Art is one of my favorite places in the world. It has 45,000 pieces spanning 6,000 years and it’s all free. You’ll see works and pieces by Goya, Matisse, Renoir, Gauguin, Church, Picasso, van Gogh, Warhol, Tiffany, Faberge, and more. Check out the latest exhibit (which usually requires a ticket) or stop by at one of their Mix events. Tours are offered and the restaurant and café are open late.

From the museum, Little Italy is just a short drive (or walk if it’s warm outside) away. Try the calamari antipasti at La Dolce Vita. Have a traditional sit-down Italian dinner at Trattoria on the Hill. Think lasagna, chicken picatta, and seafood pasta. Then stop by either Presti’s Bakery for cappuccinos and dessert or Corbo’s Bakery for the cannolis.

West Side Market & Great Lakes Brewing Company

Tucked away in the Ohio City neighborhood of Cleveland is the West Side Market, an indoor/outdoor market featuring over 100 vendors. Admire the 44-foot high Guastavino tile vaulted ceiling and 137-foot clock tower. On one side of the market there is a staircase that leads you to a second-floor balcony where you can get the best selfie or photo overlooking the market. Sample meats, cheeses, fruits, and vegetables from local vendors. If you’re traveling from afar, bring a cooler to take home seafood, homemade pastas, and premade meals.

Next hop over to Great Lakes Brewing Company for a tour and a tasting. You can eat dinner there or stop by one of the other breweries or gastro pubs in the area. We like Market Garden Brewery and Bier Markt. Finish the night with Mitchell’s Ice Cream.


Mt. Washington & Altius

One of the most stunning ways to view Pittsburgh is from the top of Mt. Washington. You can get there by car and walk along Grandview Avenue, a sidewalk-lined street that features several overlooks perfect for taking photos and stopping to admire the view. Or you can ride up in the Duquesne Incline, one of the few of its kind remaining in the country. It will only cost you $2.50 one way or $5 round trip.

After getting off your cable car chariot, walk or drive to Altius for creative, seasonal dishes and fantastic views of the city. To cap off the night, visit the Summit for board games and delicious cocktails. For a sweet treat, try DiFiore’s Ice Cream Delite.

Phipps & Shadyside

Phipps Conservatory and Botanical Gardens is one of my favorite places in Pittsburgh. It features impressive seasonal shows in its 14-room glasshouse (which is impressive in and of itself) and is home to 23 distinct gardens.

After making your way through the splendor that is Phipps, head drive over to the Shadyside neighborhood for shopping and food. Walnut Street is lined with a number of cute boutiques and well-known brands, including Patagonia, Lululemon, and more. It’s also home to fun gift shops like Kards Unlimited, which basically feels like a grown-up, much more sophisticated Spencer’s Gifts, and Toadflax, a truly unique florist.

For dinner, try Tocayo for delicious tacos and margaritas. After dinner, have drinks at Le Mardi Gras, an old school lounge complete with jukebox and classic cocktails. Or try Millie’s Homemade Ice Cream.

The Cultural District & Meat & Potatoes

The Cultural District is Pittsburgh’s epicenter of great music, theater, and art. All located within a few blocks of each other are Heinz Hall, home of the Pittsburgh Symphony Orchestra, the Benedum Center, which hosts big-name musicals, the Byham Theater, which showcases dance, film, and theater, the O’Reilly Theater, home to Pittsburgh Public Theater, and the Harris Theater, another venue for live performances and movies. Check any one of these venues’ busy event calendars to find a show or performance you’d like.

For dinner, head to one of our all-time favorite restaurants, Meat & Potatoes. I haven’t had a bad meal at this restaurant. If you’re adventurous, try the Bone Marrow. Just trust me. We’ve also had and loved the pork chop, fried brussels, and any of the mussels with frites.

After dinner, walk to Sienna Mercato and go to the rooftop bar on the third floor, Il Tetto. With its retractable glass roof, you get incredible views of the skyscrapers that tower over it.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s