Wrapped In Tradition: How My Family Celebrates The Season In Southern Maryland

SOUTHERN MARYLAND — Every family celebrates the holidays a little differently. Some traditions are passed down for generations; others start by accident and just stick. That’s part of what makes this season so special — no two homes look exactly the same in December.

For my family, the way we celebrate has been shaped by place, time, and the small things that turned into tradition. I grew up in Florida, where Christmas meant palm trees wrapped in lights, warm night breezes with holiday displays, and walking outside in short sleeves. It was a completely different kind of holiday season.

This is actually our second time living in the Southern Maryland region. Years ago, we were stationed near FedEx Field in military housing, where some of our favorite traditions first began. Since then, we’ve added new ones, adjusted others, and found what works best for us as a family.

Here are a few of our holiday traditions we do every year.

No Tags, Just Paper

In our home, gifts don’t come with name tags. Instead, each family member gets their own wrapping paper design — and no one knows who’s who until Christmas morning. The guessing game has become a tradition all on its own.

Even the sibling gift gets its own wrapping paper. With a big age gap between my kids, I started picking out something each year that gives them a reason to spend time together — not always shared, but always connected. Fourteen years later, it’s still part of what we do.

To keep all these paper choices straight, I grab double-sided wrapping paper from BJ’s every year. The rolls are big, the price is great, and it gives me plenty of options to work with.

southern maryland christmas traditions

Themed Christmas Eve Pajamas

Matching pajamas? Not for us. We tried that once, and after one chaotic laundry day, I never did it again. Everyone now gets their own set — often coordinated in color or theme, but always easy to tell apart and fun to unwrap on Christmas Eve.

When they were little, the pajamas often came with a matching toy.

These days, that tradition has grown up with them. Instead of character toys, I now wrap board games or card games the whole family can enjoy together. It’s less about what’s in the box and more about making the evening fun together.

southern maryland christmas traditions
Chistmas Pajamas 2025 | Stranger Things theme

Festival Of Lights At Watkins Park

We used to live just minutes from Watkins Regional Park when my son was born, and every year we’d go see the winter light display. After moving back to Southern Maryland 13 years ago — and now living nearly an hour away — we still take the ride.

We leave in time to get there just as it gets dark, with holiday music playing and our Holiday Mad Libs book in hand. We take turns asking the prompts, filling in silly words, and I mark the year at the top of each page we finish. It’s a small thing, but it makes the drive more fun.

Seeing the park expand over the years has been part of the fun, too. The mega tree is pretty great now, and they’ve added new features that make it feel fresh every time. They even hand out a reindeer checklist game — and yes, my 20-year-old and 14-year-old still play it. Mostly for me, I think… but I’ll take it.

Festival Of Lights At Watkins Park

Teddy Ruxpin Returns

We had the original Teddy Ruxpin growing up, and every Christmas Eve he’d sing us holiday songs. A few years ago, I tracked down an original on eBay — complete with his holiday outfit and the original books. It wasn’t cheap, but it was worth every penny.

Now he’s part of my Christmas again. I play him for guests when they visit, and always on Christmas Eve. One day I’ll find a Grubby to go with him, but for now, it’s enough.

My favorite is Hark, How the Bells — Teddy Ruxpin’s take on Carol of the Bells, sung by The Anythings. It’s held its place among my holiday favorites for years. Hear it here.

teddy ruxplin's christmas tradition

And while our family traditions mean so much, it’s the people around us — especially local friends who’ve come to feel like family — that truly bring the season to life. From walking through the Kris Kringle markets, to sharing handmade cookies, to waving at our Santa on the fire truck, these small moments make Southern Maryland feel like home for the holidays.


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Jessica Jennings, a Tampa, Florida native, brings a rich and diverse perspective shaped by her global experiences as a U.S. Navy veteran and military spouse. After joining the Navy at 19, Jessica’s service...

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