As you know, we love exploring downtown areas in Chicagoland. Since the holidays are quickly approaching, I wanted to check out a downtown area that not only offered a fun downtown experience but was decked out for the holidays. I heard about the Holiday Happenings in Downtown Wheaton and couldn’t wait to see what the town offered.  

Related: Looking for more holiday activities? We always count down with an activity advent calendar. This year I listed more than 60 things to do!

Getting started in Downtown Wheaton

Look for street parking or free parking lots anywhere in Downtown Wheaton. We parked on Front Street.

Coffee stop

You know I love my coffee and any stop to a new area includes finding a coffee spot. In my search I saw My Half of the Sky serves coffee with a mission. A purchase helps “eradicate poverty while providing hope to survivors of human trafficking, homelessness, addictions or extreme poverty, locally & globally.” I was happy to see that they served a horchata latte. Not only do they serve coffee and tea, but they also have a cute retail shop.

Scope out the holiday windows

Strolling down the Downtown area we found so many windows painted. In true O the Places We Go fashion, we took photos by our favorites.

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

Search for reindeer

The main holiday highlight of Downtown Wheaton are these super cute evergreen reindeer located all over town.

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

Tip: Make sure to download the Downtown Wheaton Association map that has all the painted window and reindeer.

Lights at Adam Park

Bundle up and take a walk through Adams Park. So pretty and festive! Don’t forget to snap a pic by the big “Christmas” tree.

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

Tip: Make sure to bring your wish lists for Santa and drop it off in the Mailbox

Watch the train pass

Even though my kids are a little older, they still love watching trains pass by. Lucky for us, Downtown Wheaton has a Metra stop and on more than one occasion we saw it chug along. They even have one of those large Adirondack chairs situated perfectly for pictures.

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

Popcorn snack time

You can’t go to Downtown Wheaton and not stop by the iconic The Little Popcorn Store. It’s perhaps the narrowest store at just 49″ wide and 60 feet long. Look for the red door. During Covid, they allow only 4 masked people in at a time. For an extra treat, give the kids $1 and let them pick out penny candy.

Dinner time

Pizza is always easy (especially for take out), so we ordered from Gia Mia Pizza Bar. We took advantage of the Monday special – Neapolitan-style pizzas for half off? Yes, please! We ended up ordering Margherita, Artichoke Pesto, New England Clam, and Prosciutto. They were all so so good. My husband even said they may be his favorite Neapolitan-style pizza place. High honors for sure!

TIp: Hale Street has been closed off to traffic, and you can “dine in” in Gia Mia’s outdoor heated tent, too.

Toy shopping

Looking to do a little holiday shopping? A stop at Moore’s Toys and Gadgets is a must! They have tons of STEM items, games, and toys that we’ve never seen.

Ice cream break

Next door to Moore’s Toys is Kimmer’s Ice Cream. It’s been years since I’ve visited here. In fact, I blogged about it when they first opened up. I couldn’t wait to come here again and bring the kids. You can’t go wrong with any flavor. It’s all so good!

Check out all the holiday happenings in Downtown Wheaton. Find painted windows, festively decorated reindeer, holiday lights, and more!

You can’t go wrong with cotton candy and peppermint ice cream!

Other things to do in Wheaton

  • Got a LEGO lover? Bricks and Minifigs is THE store for them.
  • Looking for more holiday lights? Cosley Zoo will have their holiday lights set up and admission will be for free.

Have you been to Downtown Wheaton lately?

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