Fun Family Holiday Outings

Being a family of five, my husband and I often hear the phrase, “boy, you have your hands full.” Couple that with the fact that we have three rambunctious little boys? It’s enough to get people exhausted just by looking at us. Call us crazy or ambitious, but that doesn’t stop us from trekking out with all three of our kids in tow. Especially because I’m a work at home mom, I live for days I’m able to get out of the house.

Simply Every Family
Signature by Levi Strauss & Co. is available at
JeeYoung Wenglikowski with her kids
JeeYoung Wenglikowski with her son

Now that the holiday season is upon us, I love venturing out to see the lights and see the lights and hear the sounds festive events around our town. Most of our fun family holiday outings are done on the fly. Sometimes, we make a day trip out of it. It’s become a family tradition to do something festive and fun when D has a random day off work during the week. Or enjoying our weekends taking in the holiday festivities all around us.

With the cold temperatures here to stay, I love to dress the whole family in clothing that is festive, but comfortable for everyone.

Cute coats and comfortable boots are a great way to complete a stylish outfit for the boys without sacrificing practical needs. They love to walk around all over the place and keeping warm is the utmost importance during the winter months.

For me, I love a good pop of holiday color to make an outfit comfortable without sacrificing style! I am loving these Signature by Levi Strauss & Co.™ Women’s High Rise Pull-On Jeggings in rhubarb. The pop of red is so perfect for the holidays. The wide band waist is super comfortable, and the jegging cut is flattering for all body types. I styled them with a warm poncho and matching gloves. The black wedge booties and leopard print socks are a fun addition, too.

The best part of these stylish Signature by Levi Strauss & Co. Women’s High Rise Pull-On Jeggings is that I can move around freely (to chase after my kids). I am all about comfort first and these jeans are definitely comfortable to wear on any of our fun family holiday outings.

Women's High Rise Pull-On Jeggings 
Signature by Levi Strauss & Co. is available at
Signature by Levi Strauss & Co. is available at

Fun Family Holiday Outings

Whether you have one kid or three, all of the fun family holiday outings that we’ve added to our ongoing list are most likely happening in and around your town too! I’ve learned in the last six years that there are a variety of holiday gatherings and events that are family friendly and more than less likely attended by other families with kids!

Here are some fun family holiday outings that have become part of our family traditions through the years:

Visiting Downtown

We love to visit our local downtown area to visit the shops and eat yummy treats. The boys love looking for holiday decorations around town and there’s never a shortage of things to do. We visit a few times throughout the season and end up doing different things each time.

Fun Family Holiday Outings
Fun Family Holiday Outings by Simply Every
Fun Family Holiday Outings by Simply Every

Breakfast with Santa

Our kids’ schools host breakfast with Santa which we’ve enjoyed the past few years. With A now in elementary school, I’ve also looked into different places that host breakfast with Santa! There are so many options. But, the key is to pick an event out early and buy tickets because they sell out pretty quickly.

Gatherings with Friends/Family

The holiday season is a great time to gather with friends and family. I usually host a holiday dinner or two. And I try to make it out to a girls’ night with my closest friends often. It’s hard to make the time for myself, but David and I try to rotate nights to make sure that we’re able to see our friends during the holiday season, too.

Light Shows at the Zoo

Holiday light shows at our local zoo are absolutely breathtaking. The boys get so excited to see all of the lights and decorations. It’s really an amazing experience for all of us, year after year. Our local mall is an outdoor mall that features a smaller scale tree light ceremony. So we look forward to that family fun outing every year, too.

Holiday Taste Fests

There are so many great holiday events like taste fests at local eateries that are perfect for date night or a family night out. We dine out with the kids pretty regularly. So, it’s extra special to enjoy a fun event that is holiday-themed for the boys. I’ve found about the events online and through friends who live in and around our town. They are all fun and delicious and another great family tradition to enjoy during the holiday season.

Holiday Events at Museums

Kids’ museums, libraries, and movie theaters host tons of fun family events throughout the season. Since, we can’t always be outdoors during our cold months, these are a great way for us to enjoy time outside of our home. If you’re looking for a way to shake out the winter stir crazies, I highly recommend checking event calendars at your local library. They are usually free to attend and very family friendly.

Simply Every is sharing some Fun Family Holiday Outings
Simply Every is sharing some Fun Family Holiday Outings
Simply Every is sharing some Fun Family Holiday Outings with Levis
Simply Every is sharing some Fun Family Holiday Outings
What fun family holiday outings do you enjoy year after year?

Fun Family Holiday Outings

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My name is JeeYoung, a work at home mom to three boys. Consultant, Content Creator, Chaos Coordinator. This is a snippet of our happy chaos - mom life, family travel, easy recipes, home decor, and simple beauty. So happy you're here!

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