The Rockies's 6 Most Festive Downtowns For The Holidays
With the holidays quickly approaching in 2025, it’s important to take time to savor the season. Given how much there is to plan, shop, and prepare for, it’s easy for days and weeks to slip away before we can enjoy them. With that in mind, why not sneak away for a day to explore some of the Rockies' most festive downtowns for the holidays? Boasting gorgeous mountain backdrops, cozy cafes, family-friendly festivals, and one-of-a-kind stores for last-minute shopping, these 6 Rocky Mountain downtowns will help you experience the season’s magic before it’s gone.
Vail, Colorado
Mirroring the Swiss Alps and Old Bavaria, Vail transports holiday travelers to Europe without the overseas travel or costs. Located at the base of Vail Mountain in the central Rockies, this Colorado alpine town is a hit in winter thanks to its namesake ski resort. That being said, Vail’s enchanting downtown is too magical to miss around the holidays. Backed by snow-capped peaks, the pedestrian-only Vail Village transports guests to Europe with its traditional alpine architecture and heated cobblestone roads. With warmth underfoot, its chalet-style boutiques, cafes, and window displays can be enjoyed with a hot chocolate in hand.
December is the best time to see the holidays come to life in Vail Village. Lights are strung from buildings, old-fashioned lamp posts are wrapped with garland, and evergreen arches add romance to your stroll. Grab a coffee or cocoa at Treff Café and window shop to your heart’s desire. Holiday stores like The Gilded Spruce specialize in nutcrackers and ornaments, or you can wait for events like the chic and cozy Vail Kris Kringle Market. Taking place December 11 to 14, 2025, vendors and artisan booths will line downtown Vail Village, selling handcrafted gifts and holiday treats. On December 7, 14, and 21, families can also bring their kiddos to snap a photo with jolly Saint Nick at the Vail Village Smile with Santa event.
Estes Park, Colorado
Estes Park is another charming Colorado town where mountain scenes and holiday traditions merge like white and red on a candy cane. With Rocky Mountain National Park right in its backyard, most know Estes Park as a "Gateway to the Rockies.” Nevertheless, come late November, snowshoe trails take a backseat to its spirited downtown. The day after Thanksgiving, Estes Park’s Annual Catch the Glow Parade kicks off downtown festivities with marching bands and holiday floats. But don’t fret if you miss the fun, since Bond Park offers a free light show every evening through the holidays. A centerpiece of downtown, the park spotlights its famous 36-foot pixel pine tree daily from 5 to 9 PM, pairing holiday tunes and choreographed lights.
Holiday cheer extends to the rest of downtown Estes Park's walk-through displays and twinkling lights. With over 300 shops strewn throughout town, the district is also a great center to get your holiday shopping done, especially if you want to support local businesses. Shops like Trendz at the Park specialize in Colorado clothing and gifts, showcasing local artists like Down to Earth Pottery. Alternatively, if you want a gift for your favorite bookworm, the Macdonald Book Shop is an indie darling set right in the heart of downtown. Nearby, the Old Fashion Candy and General Store also has your stocking stuffers covered for the sweet tooths in your life.
Park City, Utah
High in the Wasatch Mountains of Utah, Park City is a former silver mining town centered around its Hallmark-movie Main Street. While most stop by Park City this time of year for its world-renowned ski slopes, downtown is where the holiday magic happens. Whether visiting the Park City Mountain Resort or Deer Valley Resort, Main Street is a fun and festive follow-up. Over 200 businesses line the strip, housed in a mix of 19th and 20th-century buildings. Even with the addition of modern holiday lights, the historic thoroughfare has a warm, vintage feel, inspiring guests to slow down and enjoy the charms of an old-school downtown.
While the once-prominent American Main Street has largely disappeared, Park City keeps this national tradition alive. Instead of online shopping or drive-through dining, why not spend a few hours at mom-and-pop shops and restaurants like the Flight Boutique and Flanagan's On Main? Along the way, you can also admire seasonal displays, from the Silver & Snow Holiday Window Contest entries to the Snow Globe Art exhibits. As for holiday events, on December 12, 2025, kids can meet Santa after his unique arrival on the Main Street Town Lift. Alternatively, adults may prefer the holly-jolly Santa Pub Crawl, taking place on December 6.
Big Sky, Montana
Situated in the Rocky Mountains of southern Montana, Big Sky is another picture-perfect resort town whose downtown springs to life during the holidays. While its namesake ski resort is its biggest draw in the wintertime, downtown Big Sky is where families come to celebrate the season. From December 12 to 14, 2025, the Annual Big Sky Christmas Stroll will kick off the holidays in a big way. A cherished tradition for 28 years, the event will feature performances and activities for the whole family, from classic caroling to a unique holiday fireworks show.
For the first 2 days of the Stroll, all festivities are right downtown. Day 1 will take place at Meadow Village, the first stretch of downtown coming off the highway. The neighborhood will host a Tree Lighting Ceremony, Photos with Santa at American Bank, Horse-drawn Wagon Rides, and Christmas Carolers. As for Day 2 of the Big Sky Christmas Stroll, the Town Center will host the second round of fun. Surrounded by Lone Mountain’s 11,000-foot peaks, the Town Center is absolutely gorgeous in the winter. This portion of downtown will host its own festivities, including a Town Center Tree Lighting Ceremony, a Big Sky Winter Market at the Wilson Hotel, and a holiday Fireworks Show at Fire Pit Park.
Jackson, Wyoming
The holidays are just as bright in Jackson, a Wyoming town that loves to celebrate as much as it loves to ski. Situated in a valley between the Teton and Gros Ventre mountains, Jackson is home to the renowned Jackson Hole Mountain Resort. But much like these other Rocky Mountain ski towns, you’ll have to head downtown for holiday fun. At its center, the Jackson Town Square is where much of the seasonal magic takes place. The park’s 4 iconic elk antler arches will be brightened with Christmas lights, paired with plans to install a public skating rink below them on December 25, 2025.
Santa Sightings will also take place daily at the Town Square StageStop Building from December 13 until Christmas Eve, with music, hot cocoa, and holiday cookies. On December 20, Hanukkah celebrations will follow, with a Grand Menorah Lighting, Gelt Drop, Chanukah treats, and storytelling. For fun beyond Town Square, the downtown Jackson Hole Playhouse has countless holiday shows in store, including Christmas at the Playhouse from December 10th to January 3rd. Nearby, for those 21 and older, the Western-themed Million Dollar Cowboy Bar will also host a Naughty or Nice Christmas Party and a New Year's Eve Celebration in 2025.
Ouray, Colorado
Back in the Rocky Mountains of Colorado, Ouray is our final town to explore, and arguably the best for families. Encompassed by the beautiful San Juan Mountains, Ouray is known as “Switzerland of America” and “Outdoor Recreation Capital of Colorado.” However, on December 6, Yule Day festivities will take center stage with a wealth of family-friendly, festive fun. Main Street, downtown’s historic heart, will host the day’s events. Backed by rolling hills, the 19th-century strip will be decked with lights, wreaths, and other merry decorations for the Main Street Business Decoration Contest.
Yule Day fun will extend indoors at Main Street landmarks like the Wright Opera House. The historic structure will feature a cozy Hot Cocoa Bar, Cookie Decorating & Letters to Santa, and a holiday movie showing of Elf. From 11:00 to 4 PM, a Main Street Christmas Market will also take place at Centennial Park next to the Elks Lodge. Afterward, a tree lighting will follow at 6:15, marking the end of the Main Street Yule Day Parade, which is set to begin at 5:30.
Holiday Magic In The Rockies
While most of these Rocky Mountain towns are ski destinations, you don’t need to hit the slopes to get the most out of your visit. With life so full of chaos around the holidays, something as simple as a downtown stroll can feel all the more magical. Paired with snow-capped mountain views, sparkling lights, warm drinks, and warmer people, these 6 festive downtowns will help you forget the stress of the season and remember the real reasons to celebrate.
