• themadisongreer

8 Pittsburgh holiday date ideas you should try this winter

Updated: Nov 22, 2019

When I was a senior in high school, a group of my friends and I decided to go to Light Up Night in Pittsburgh. Don't get me wrong; the lights were so beautiful and the fireworks were pretty rad, too (not to mention it was totally free). But the CROWDS. It was so hard to move ANYWHERE.

That being said, there are a ton of other date night ideas that I wanted to share with you!

It's time to get all warm and fuzzy on the inside, and brave the cold on the outside!


1. Phipps Conservatory & Botanical Gardens Christmas Lights

Who doesn't like to drive around and look at Christmas lights? My boyfriend, because gas prices. This is the perfect happy medium! Buy your tickets online for an unlimited amount of Christmas lights as far as the eye can see! Phipps Conservatory, located in Schenley Park, is made up of multiple green houses and gardens that sit on fifteen acres of land. Just imagine thousands of lights wrapping around all of its greenery! It's a little difficult to just go out on a whim and show up without tickets, though. When you go to their website, they say you have to buy tickets in advance to see the lights. Once you pick a date and a time, you also have the opportunity to get discounted tickets using your student ID! The Phipps Conservatory is my favorite place to go to get into the holiday spirit!

PRICE: $16.95 with your student ID, $17.95 regular admission

2. Ice Skating at PPG Place

For a little bit cheaper and more spontaneous fun, I love to go ice skating! Right in the middle of Market Square is an ice rink surrounding a huge Christmas tree. It's best to go during the day when everyone else is at work, but weeknights still prove to be less crowded than Fridays and Saturdays. You can skate for as long as you want! When you're done, you can head over to the Peoples Gas Holiday Market down the street and help yourself to some food and hot chocolate!

PRICE: $10, with an additional $4 if you need to rent a pair of skates.

3. Pittsburgh Penguins Game

Okay, okay, it's not really a holiday date. But it's winter, and it's a hockey night in Pittsburgh! (I don't know about yinz, but I'll be sporting my Fleury Winter Classic jersey). Remember when I said that Phipps was my favorite holiday date? Just kidding. Sid is my number one.

PRICE: Depends on the game, where you sit, etc. etc. etc... (but totally worth splurging on if you can *wink wink*)

4. Kennywood's Holiday Lights

If the botanical gardens aren't your style, you can head over to Kennywood to see their holiday lights! On certain nights, you can also have dinner with Santa (be sure to check their website for exact dates!). While the Phantom won't be running, plenty of slower rides brave the cold and the snow, like the Kangaroo, Noah's Ark, and the merry-go-round. They also play Christmas music throughout the park and do lightshows during the evenings.

PRICE: $16.99 if you go on a Friday or Sunday night, and $17.99 the rest of the time!

5. PPG Place's Wintergarden and Gingerbread House and Train Exhibition

Right next door to the ice rink, you'll step foot into a gingerbread wonderland. Personally, gingerbread houses aren't my style (they are so frustrating!), so looking at the hundreds that people around Pittsburgh make gives me a sense of satisfaction (and maybe a little sorrow/anger). It's a great way to warm up after ice skating! Get yourself a hot chocolate at their stand and pick your favorite house!

PRICE: Free!

6. The Gateway Clipper Fleet

Although my boyfriend and I have never done this together, I once did this when I was younger and it was so much fun! The Gateway Clipper fleet offers rides and dinners all year round, but during the holiday season, you can catch Santa in attendance! Not interested in Santa? They have a ton of other options to choose from, including a Holiday Captain's Dinner! I think it would be an incredibly romantic date to travel the three rivers surrounded by lights and Christmas music.

PRICE: Price varies depending on which cruise you go on, but tickets start at $24.

7. CLO Holiday Performances

I know, I know. Musicals and plays aren't everyone's scene, but as a former theatre nerd (I was Jane Banks in Mary Poppins my junior year of high school and it's one of my proudest moments haha), I live for them! The Pittsburgh Cultural District performs renditions of The Nutcracker, A Christmas Carol, and several others every year. There's bound to be one that you'll enjoy!

PRICE: Depends on the show, where you sit, etc. etc. etc.

8. Put a lock on the Roberto Clemente Bridge

What can I say? At this time of year, we all tend to be a little cheesy. You can't beat putting a lock on the bridge and tossing the key overboard. This holiday season, pair this cheese with a bold red; because it's 2018 and we all deserve it.

PRICE: Free, but you have to buy your own lock obviously!


I hope these ideas gave you some of your own, and I'd love to hear about them if you have any holiday spirit to share! If I missed any of your favorites, please let me know!

And don't forget to end each and every date with a Primanti's sandwich!

I love this time of year and the dates that I drag my boyfriend on! Him, not so much... but he’s a good sport!

xoxo, Madison

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