Downtown Colorado Springs transforms into a winter wonderland each December. Strings of lights dance across Victorian-era buildings, the crisp mountain air carries hints of pine and peppermint, and the streets come alive with holiday magic. This year, the city is offering an incredible lineup of festive experiences that go far beyond typical seasonal activities.
Whether you’re planning a romantic date night, organizing a friends’ outing, or creating new family traditions, these six adventures showcase the very best of Colorado Springs’ holiday spirit.
Check availability using the links below and book soon as most of these events in downtown Colorado Springs will sell out!
Best For: Families with children, large friend groups, corporate holiday parties, and anyone looking for a photo-worthy experience that accommodates multiple generations.
The Holly Jolly Christmas Trolley hosted by Adventures Out West is a festive 20-minute ride through downtown’s sparkling streets. The vintage-style trolley is lit from top to bottom with holiday lights, creating the perfect backdrop for festive photos.
Book just two seats for an intimate experience, or reserve all 14 spots for an exclusive holiday party. Add Skate in the Park tickets to extend your adventure, or book the entire trolley for a corporate event. Operating from Thanksgiving through New Year’s, this experience captures everything we love about the holidays.
Best For: Couples seeking a romantic evening, anniversary celebrations, engagements, or anyone wanting an intimate, Instagram-worthy winter date experience.
The “Holi-Date Night” Package combines two activities you can enjoy on your schedule. First, settle into your private Cozy Coach—an open-air Jeep transformed with soft fur hides, twinkling Christmas lights, vintage lanterns, and heated seats wrapped in plush wool blankets.
Your 20-minute guided ride winds through downtown’s most charming streets where historic architecture meets holiday decoration. After your coach ride, redeem you two included tickets to Skate in the Park at Acacia Park. The perfect cap to the perfect winter date night!
Best For: Small families, double dates, close friend groups, or anyone wanting to share a magical twilight ride through downtown in an intimate, festive setting.
Have more people? The Cozy Coach Ride for up to 4 guests delivers the same magic with space for your favorite people. This 20-minute guided ride showcases downtown at twilight in a festive Jeep retreat complete with fur hides, twinkling lights, vintage lanterns, heated seats, and plush blankets.
Think alpine lodge meets holiday sleigh ride—without the snow in your boots. Add Skate in the Park admission to extend the magic.
Best For: Outgoing friend groups, bachelorette parties, colleagues looking for a unique team outing, and anyone who loves to sing (talent optional!) and enjoy craft cocktails in a festive atmosphere.
The Caroling & Cocktails Tour is a delightful mashup of bar-hopping and carol-singing. Over two fun-filled hours, you’ll visit three lively bars. Each serves a seasonal holiday cocktail paired with appetizer bites—just enough to keep the caroling strong.
Armed with songbooks, you’ll stroll through twinkling downtown streets spreading cheer. Limited to just 12 guests, the tour starts at the historic Mining Exchange Hotel. Your local guide—affectionately called a “Taste Bud”—keeps the energy high while sharing insider knowledge about each venue and the city’s history.
Your all-inclusive ticket supports Care and Share Food Bank for Southern Colorado. This December-only experience runs throughout the month.
Best For: Craft beer enthusiasts, burger lovers, casual small groups, dad-friendly outings, and anyone who prefers hearty food over fancy fare while exploring local breweries.
The Jingle Bells, Burgers & Brews Tour celebrates two Colorado favorites: exceptional craft beer and seriously good food. This December-only, two-hour adventure visits two local craft breweries and one award-winning burger spot.
You’ll savor at least three Colorado craft beer tastings—seasonal and signature brews. The food is hearty: an award-winning burger with fries, BBQ chicken slider with potato salad, and a handmade pretzel knot from a locally acclaimed bakery.
Starting at Mash Mechanix Brewing Co., this walking tour is limited to just 12 guests for that intimate, VIP experience.
Best For: Foodies, couples celebrating special occasions, small groups wanting an upscale holiday experience, and anyone seeking a meal-replacement tour with sophisticated seasonal flavors and festive ambiance.
The Holiday Lights & Bites Progressive Dinner is Rocky Mountain Food Tours’ signature holiday experience. It sells out almost every year.
This 2.5-hour progressive dinner features four delicious courses: three savory stops and one sweet dessert finale. Two alcoholic beverages are included—a Colorado craft beer or cider at one stop and a festive cocktail at another. Mocktail options are available.
Limited to 12 guests on select December nights, the tour departs from the elegant Antlers Hotel. You’ll “dine and dash” progressive-style while your guide shares stories about Colorado Springs’ culinary scene and history.
The menu changes annually, making this the foundation of a new holiday tradition you can return to year after year.
With so many incredible options, choosing which experience to book first is tough. These tours book up quickly as December progresses. Securing your spot early is the way to go.
Most experiences offer flexible cancellation policies. Several now feature Afterpay options so you can reserve seats without paying in full upfront. Whether you’re planning a date night, organizing a friends’ outing, hosting a corporate holiday event, or searching for that perfect gift, these experiences deliver memories that last.
This December, let downtown Colorado Springs show you what the holidays are really about: connection, celebration, and the simple joy of experiencing something magical together. From vintage trolleys to progressive dinners, from ice skating to carol singing, the perfect holiday adventure awaits.
Ready to book your holiday magic? Visit Rocky Mountain Food Tours to reserve your spot before these limited-edition experiences sell out!
Rocky Mountain Food Tours is the most fun thing to do in Colorado. We are proud to promote other exceptional Colorado experiences. When you book a downtown Colorado Springs trolley through our recommendations, you’re supporting local businesses while discovering the best of what our state has to offer.
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