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Cleveland Date Night Guide: Playhouse Square

Welcome to the Cleveland Date Night series! This series will highlight some fun date night ideas in and around Cleveland. Find more date night ideas here.

When I think “date night” in Cleveland, one of the first things that comes to mind is going to a show at Playhouse Square.

Playhouse Square is the second-largest performing arts center in the United States; only Lincoln Center in New York City is larger. So it’s no surprise, then, that there’s something to do or see at Playhouse Square almost every night of the year!

A Playhouse Square date night is pretty straight-forward: I recommend drinks, dinner, and then a show. But in case you haven’t been to Cleveland’s theater district recently, here are some specific (and hopefully helpful) tips to help you plan the ultimate night out.

Step 1: Go out for drinks

Whether you’re meeting up after work or going on a weekend, first up it’s time for some drinks!

I recommend the Azure Rooftop Lounge, atop Metropolitan at the 9 on East 9th St. This rooftop bar is only about a 7-minute walk from Playhouse Square, and offers up fantastic downtown views.

Azure Rooftop Lounge in Cleveland
Downtown views at Azure
Azure Rooftop Lounge in Cleveland

Azure has a large and breezy rooftop with plenty of seating and a large bar to order from. Reach it by entering Metropolitan at the 9 and taking the elevator to the top floor.

Azure Rooftop Lounge in Cleveland

If a rooftop bar isn’t your speed, check out Bin 216, which is connected to the Palace and State theaters. Bin 216 is a great place for wine and small plates.

Step 2: Enjoy dinner downtown

There are a lot of great restaurants to choose from within easy walking distance to Playhouse Square. Some of my favorites include:

Adega2017 E. 9th St. – Since you might hit up Azure for drinks anyway, consider checking out Adega, the in-house restaurant at Metropolitan at the 9. Adega offers Mediterranean-inspired plates, from seafood to pasta.

District1350 Euclid Ave. – This airy and modern spot serves up delicious American fare. I like it for a pre-show dinner because all of their signature drinks are named after songs from Broadway musicals!

Hofbräuhaus Cleveland1550 Chester Ave. – Who doesn’t love Hofbräuhaus? Here you’ll find craft beer, traditional German food, and live music in a beer garden atmosphere.

Cibreo Italian Kitchen1438 Euclid Ave. – This is a Tuscan-themed restaurant serving up traditional Italian dishes just steps from the theaters of Playhouse Square.

Puente Viejo1220 Huron Rd E – A modern spot serving elevated Mexican fare and hand-crafted margaritas.

Cowell & Hubbard1305 Euclid Ave. – This modern French restaurant is located in a historic building that used to house one of the city’s top jewelry stores. Cowell & Hubbard is a restaurant by Cleveland chef Zack Bruell.

Note: I definitely recommend making a reservation for most of these spots in advance! And let them know when you arrive that you have a show to catch; they’re all very good about making sure you’re not late!

Step 3: See a show

And now for the main event: a show!

Connor Palace theater
Come From Away at Connor Palace

There are tons of events and performances that happen at Playhouse Square every year, ranging from Broadway musicals to comedy shows to lecture series. No matter where your interests lie, you’re pretty much guaranteed to find something you’ll like.

Some things I personally love include:

Keybank Broadway Series – Playhouse Square plays host to around 10 touring Broadway shows per year. And we’re talking major shows, too! Last year Hamilton came to town, and in 2020 we’re getting Frozen!

Hamilton at Playhouse Square

National Geographic Live – Ever wanted to hear about some of the world’s most incredible places straight from Nat Geo photographers? Then this speaker series is for you.

Cinema at the Square – If you’re looking for something slightly easier on the budget, check out what’s playing during Cinema at the Square. This annual summertime series (happening in August this year) shows more than a dozen movies on a big screen inside the beautiful Connor Palace theater. Tickets are just $5 each!

And of course there are plenty of one-off concerts and comedy nights to look out for, too!

Check out the full Playhouse Square line up on their Event Calendar.

Where to park at Playhouse Square

The bad news is that you won’t find any free parking near Playhouse Square. But the good news is that there are lots of parking options to choose from.

Playhouse Square at night
Did you know Playhouse Square has the largest outdoor chandelier in the world?

The cheapest options are often the surface lots on Chester and Prospect. I’ve parked for as little as $10 before.

There are also garages all along Chester, Prospect, and 14th, which vary in price. (Real talk: You’re likely to run into “special event pricing” almost any night you try to park downtown since we have 3 different sports teams that all play in stadiums that are within walking distance to Playhouse Square. Expect to pay $20+ in these garages.)

The most convenient place to park is in the designated Playhouse Square Parking Garage (1450 Chester Ave.), which is connected by covered walkway to the theaters. This lot is $20 on site, but you can save a few dollars if you purchase your parking online in advance (you can add it on when you buy your tickets).

Do you have any other date night tips for Playhouse Square?

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Date night at Playhouse Square in Cleveland

This Post Has 2 Comments

  1. Catherine

    Just discovered your blog. New to Cleveland and loving the info.

    1. Amanda

      Thanks, Catherine – and welcome to Cleveland!

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