Holiday Magic for Little Ones: Our Favorite Family Outings 🎄

“Every good and perfect gift is from above, coming down from the Father of the heavenly lights.”

— James 1:17

The Christmas season is a wonderful reminder of God’s blessings and the gifts of family, joy, and love. Even the smallest traditions can become meaningful memories that teach our children about gratitude, hope, and the beauty of celebrating together. As a family with a toddler and a baby, we cherish the little moments that bring the holiday spirit to life, the wonder in their eyes, the laughter that fills the air, and the sense of peace that comes with celebrating together.

December is such a special time when even a simple outing feels like stepping into a storybook, especially with little ones in tow. Over the years, we’ve built family traditions around certain events and places that always bring joy, wonder, and plenty of giggles. Here are some of our favorites, along with the memories that make them so magical.

Yesteryear Farms

One of our first stops in December is always Yesteryear Farms. Our toddler’s eyes lit up when we met Santa and Frosty the Snowman. Baby snuggled in my arms, taking in the twinkling lights, while our little one laughed and waved at Frosty. It is a simple outing, but one that fills the heart with Christmas cheer.

Merrywood Farm

At Merrywood Farm, we loved riding the horse and running through the Christmas tree field. Our toddler squealed with delight as we wandered between the trees, and toddler seemed to enjoy the motion of the horse ride while quietly watching the world go by. It is the perfect mix of excitement and calm for a family with little ones.

Snowflake Lane Parade

The Snowflake Lane Parade requires a bit of a drive, but it is absolutely worth it. The floats, lights, and performers reminded us of the game Candy Cane Lane, and our toddler clapped nonstop. Even baby seemed captivated by the sights and sounds. It is a festive, well-executed parade that feels magical for all ages.

Winter Wonderland at Sunset Lane

One evening, we packed the car and drove through Winter Wonderland while singing Christmas carols the whole way. The sun was just beginning to set, casting a warm glow over the lights. I recommend going earlier if you have small children because the sunset adds a magical touch and the experience is much more enjoyable when the little ones are not too tired.

Holiday Express in Downtown Portland

The Holiday Express train is perfect for small children. It is less stimulating than some of the larger events but still full of Christmas magic. Our toddler loved spotting the twinkling lights along the route, and baby enjoyed the gentle motion of the train. It is an easy, festive experience that leaves everyone feeling joyful without being overwhelming.

Polar Express at Mount Hood

The Polar Express performance is based on the beloved movie, and the performers do an incredible job bringing the story to life. Our whole family felt like we had stepped into a storybook. Our toddler was wide-eyed with excitement, and even baby seemed enchanted by the sights and sounds. It is a must-see for families who want a more immersive Christmas experience.

Frog Pond Farm

Frog Pond Farm is one of our favorites for its mix of animals and intimate experiences. Even though the farm can be busy, it is large enough to feel like you have your own space at times. Our son loved seeing the camels and excitedly asked if those were the ones the three wise men rode to see Jesus. It is a perfect combination of education, fun, and wonder for little ones.

Storytime with Mrs. Claus at Washington Square Mall

Storytime with Mrs. Claus is so much fun. She reads wonderful Christmas stories while her elves and interpreters bring the tales to life. After storytime, she stays to take pictures with the kids and treats them with warmth and care. Our toddler could not stop talking about the stories, and baby just smiled, captivated by the colorful characters.

Christmas Ships along the Willamette and Columbia Rivers

Watching the Christmas Ships is a family tradition I have cherished since I was my son’s age. We usually get dinner at the waterfront and watch the ships from the window. I recommend making a reservation. Seeing the boats all lit up, our toddler pointing in awe, and baby snuggled against me was a moment of calm and magic we will never forget.

TVFR Santa and Fire Trucks Event

This was one of the most memorable outings for our toddler and is probably his first Christmas memory. Santa arrived in a firetruck, we got to sit on his lap, and then we even rode in a firetruck ourselves. It was exciting, fun, and unforgettable. Even though we did not make it last year, our son still talks about it with delight.

Why These Outings Matter to Us

Having a toddler and a baby changes the way you experience the holidays. Long lines, loud crowds, and overstimulation are not worth it, but gentle magic, warm traditions, and little moments of joy are priceless.

Every time we visit one of these places, we are not just out for a “fun day.” We are building memories. We are creating small traditions. We are giving our kids a sense that Christmas is not just about gifts; it is about connection, wonder, and being together.

Here is to a holiday season full of joy, wonder, and sweet family memories. ❤️