When the holiday season hits the east metro, there’s no shortage of twinkle lights, cheerful music, and kid-friendly memory-makers. Families around Woodbury can fill their calendars with sweet meet-and-greets with Santa, storybook tea parties, dazzling train rides, and a classic stage show that makes hearts grow three sizes. If you’re looking for festive, low-stress ideas that your preschooler will love, start with these local favorites.
The City of Woodbury has hosted a sweet, small-scale celebration where little ones decorate cookies, create a simple holiday craft, and snag a photo with the Big Guy himself, all in a cozy, parent-friendly setting at Eagle Valley Golf Course. Recommended for ages two and up, this type of city-run event keeps the focus on hands-on fun and calm holiday magic (think sprinkles, glue sticks, and big smiles). If your preschooler thrives with short activities and gentle transitions, it’s an ideal pace and place. Keep an eye on the city calendar for details and registration windows, as these sessions can be popular.
Fans of the beloved Parisian schoolgirl will adore this dress-up tea party inspired by Madeline’s Christmas. Hosted by Merrill Arts Center in Woodbury, the experience layers costumes, treats, and themed activities for a delightfully civilized holiday hour with your child. It’s a low-pressure introduction to live arts settings, perfect for wiggly preschoolers who love make-believe and storybooks. Dates typically land across early-to-mid December—watch for ticket releases and note that some sessions sell out quickly.
All aboard a vintage railcar for a short, sparkling ride to the North Pole! Operated by the Friends of the 261, the North Pole Express brings holiday nostalgia to life with restored train cars, Santa and his cheerful elves, and cozy touches like hot chocolate and cookies at the depot. Little train lovers will be wide-eyed from the moment the conductor calls “tickets,” and parents will appreciate the smooth logistics and photo-worthy backdrops. Tickets tend to disappear fast, so plan ahead if this is on your wish list.
If “free and festive” is your love language, Santa’s Workshop at the historic Landmark Center is a gem. Families can snap a complimentary photo with Santa, then stick around for drop-in games, hands-on gift-making, and even a visit with friendly animals—perfect for preschoolers who move quickly from one activity to the next. The stately building turns delightfully playful for an afternoon, and the come-and-go format keeps things flexible for nap times. Check dates and details before you head out.
For a big, sparkly dose of storytime-come-to-life, head to Minneapolis for CTC’s beloved production of How the Grinch Stole Christmas! With colorful Whoville sets, music that gets little toes tapping, and a heart-warming finale, it’s a joyful entry point to live theatre for young audiences. CTC provides clear age guidance and performance info so you can pick the time that works best for your family. Make a mini day-trip of it with an early show and hot cocoa afterward.
From cookie-decorating and storybook tea parties to vintage train rides, free downtown fun, and a classic holiday musical, the Woodbury area makes it easy to celebrate the season with little kids in tow. Choose one (or several!) that fit your family’s pace, and you’ll capture the kind of cozy, joy-filled moments that make December feel magical. And while you’re planning festive outings, give your child a nurturing, consistent place to learn and grow all year long, Peace of Mind in Woodbury offers infant care, toddler care, preschool, and Pre-K in a safe, educational, and fun environment. Schedule a tour to see the classrooms and meet the team.
Photo by Jasmeen Hemmings on Unsplash
