Let’s Explore! Winterland at Park at Wrigley (now Gallagher Way)


My promise to Luke when he was born was that I would try to provide him with the best childhood experience. Something more than material possessions (i.e., toys). Something my parents gave me – fun family memories. As a mom, one of the most rewarding experiences for me is seeing Luke’s eyes light up when he experiences something new.  The excitement on his face just does it for me. In that one moment, all my mom guilt and “mom fails” are gone. I have done something right. I am fulfilled.

On Sunday, we took Luke to the Park at Wrigley (now known as Gallagher Way) for one of our family winter adventures. I got to see Luke enjoy his hot chocolate with his own snowman mug (he looked like a grown up doing it), try to ice skating again, pick out an ornament for our Christmas tree at Christkindlmarket, and run around the Park at Wrigley (now known as Gallagher Way) with the iconic Wrigley Field as the backdrop.


The Park at Wrigley is located right next to Wrigley Field in the Lakeview neighborhood of Chicago.  Recently, the Park at Wrigley has been transformed into “Winterland at the Park,” with an ice rink, a Christkindlmarket, Santa’s Workshop and some fun restaurants.

It’s amazing how the area around Wrigley Field has changed. I know there are street festivals in the summertime there but I never thought there would be a winter festival right next to Wrigley Field! But you know what? It works! I think it’s a great addition to the neighborhood and a fun place to spend a winter day in Chicago.


I really hope I fulfilled some of that promise to Luke on Sunday in that he will look back and remember the first time he went to Winterland at the Park at Wrigley. We didn’t get a chance to see Santa, but we plan to go back again…before Christkindlmarket ends on December 31st or when the ice rink closes on February 25th. Until then, here are some highlights from our day there from this past Sunday.

Christkindlmarket at the Park

Since this is Chicago’s Christkindlmarket, we had to start our adventures off with some hot spiced wine (Glühwein, to be exact) and hot chocolate for Luke. And then try some of the food there as well.  Our favorites were the apple strudel at from The Stackery and the baked cheese sandwich with ham from the Baked Cheese Haus. The shopping came next!


Christkindlmarket at the Park is the second Christindlmarket location in the city. It felt like neighborhood Christmas market and looked like somewhere out of a small European town. It’s also kid-friendly as we had room to move around, there are drinks and food for kids, and lots of places to sit.

The Rink at the Park

I think it’s pretty cool that there’s an ice rink at Park of Wrigley or next to Wrigley Field, to be exact. I knew we had to go ice skating while there and I was pretty surprised that Luke wanted to ice skate when he saw the rink (he tried it last year for the first time and did not like it). So we rented our skates and headed to the rink after we stuffed our faces with food.


Since we knew Luke couldn’t skate on ice by himself, both Charlie and I held his hands and skated by his side around the rink once. I was kinda scared since I haven’t ice skated in a very long time. But it’s like riding a bike.


We could tell Luke was struggling so I asked him if he wanted to take a break go see Santa instead. He told me he wanted to stay on the rink and learn to skate. He held onto the side rails and went around the rink three times on his own while Charlie and I stayed very close by him. He did not give up. At that moment, I saw this strong feature within him shine through. I saw his resilience. He was so happy he finished going around the rink on his own. I couldn’t help but cheer for him as loud as I could because I will always be his biggest cheerleader. Both Charlie and I were so proud of him for trying.

The Views at the Park 

After ice skating, we went up to the patio to take in the views of the Park at Wrigley. It was fun to watch people ice skate and point out Chicago’s skyline to Luke. A stranger asked if we wanted a family photo. We happily accepted and so glad we did! It was the perfect backdrop to remember the fun day.


Taking it All in at the Park

This holiday season, my goal is to try to stay present or be in the moment. I’m trying to put my phone down and take it all in because being in the moment is so important and these moments don’t last forever. Although we did take some pictures and I posted snippets of our day on my Instagram stories, I did manage to stay present when I needed to and it felt good. It was fulfilling to skate with Luke and watch him not give up, to be outside on a warm December day, to end the day on the patio and just take in the scenery…a winter wonderland. Most importantly, it was fulfilling to make fun family memories together. And staying present in those moments is the best holiday present.


Thank you the Park at Wrigley for partnering on this post. All photos and opinions are my own. 

5 thoughts on “Let’s Explore! Winterland at Park at Wrigley (now Gallagher Way)

  1. jpiraro says:

    What a wonderful day! Luke is so Lucky to have you guys as parents! Your so fun and give him so many wonderful experiences AND both work which is no easy feat!

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