City Guides US & Canada

3 Unconventional U.S. Cities to Spend the Holidays

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There is no shortage of exciting places to spend the holiday season around the United States, from cozy little towns in the frozen tundra to warm-weather locales that still know how to tap the seasonal traditions in style. For anyone looking to travel for an unforgettable holiday trip, consider these three options that offer an incredible spread of possibilities catering to a variety of interests.

1. Colorado Springs, CO

Jingle Bell Run 5K and Kids’ Reindeer Romp

From romance to family-friendly events, Colorado Springs is always a magical place to visit when fall finally gives way to winter. At a sprawling costume party and holiday celebration rolled into one, the Jingle Bell Run 5K and Kids’ Reindeer Romp is one of the main events that kicks the season into high gear. Participants toss on their ugliest ugly-Christmas sweaters, Santa suits, and reindeer antlers for an energetic run (or stroll) through scenic Fountain Creek Regional Park, which lies at the base of the snowcapped Rocky Mountains. The fun run also is for a great cause that will help you get into the holiday giving spirit, as the proceeds go to a variety of programs that help local teens.

While the Jingle Bell Run 5K is perfect for families, couples, or individuals, the same goes for the popular Skate in the Park, a growing tradition at Acacia Park in downtown Colorado Springs. Featuring demos by Olympic skaters and programs for skaters of all ages and skill levels, Skate in the Park is circled by holiday lights and dwarfed by the surrounding mountains. Families also tend to go all-in for the Santa Express Train, where patrons toss on their favorite holiday pjs and enjoy hot cocoa and cookies with Santa on the way to the North Pole.

Spend the Day at a Castle

On top of the robust list of family options in Colorado Springs during the holidays, there are also some great opportunities for small groups or couples looking to drum up a little romance. At Glen Eyrie, you can not only have a cozy night in a real castle, but you can also participate in a range of holiday activities, from the very popular Yule Tea to the immaculately decorated Madrigal Banquet, which will whisk you back to the 16th century for a jolly night of great food and activities. Also in the area, Miramont Castle offers a Victorian-era Christmas atmosphere from mid-November onward, creating another beautiful backdrop to get the season rolling in the right direction.

Also consider: For more than three decades, the Festival of the Lights Parade has taken over downtown Colorado Springs with a wondrous spread of lights and holiday spirit. The Cheyenne Mountain Zoo’s Electric Safari also pivots to the holiday season with all kinds of impressive decorations and offers outstanding views of city holiday lights from its mountain perch.

2. San Diego, CA

You may not instantly think of Southern California when you conjure up images of the holidays, but one trip to San Diego at the right time of year can change that in an instant – particularly for anyone hoping to escape the more wintery aspects of the holiday season. Over at the renowned Hotel Del on Coronado Island, you can actually walk right along the ocean all the way up to the Del’s famous outdoor ice-skating rink, where holiday enthusiasm runs rampant throughout December and early-January. Staged between the wide Coronado beaches and the famous red rooftops of Hotel Del, the rink offers California-style ice skating that typically comes with mild weather (think low to mid-60s) and the patented San Diego sunshine. Hotel Del also gets very decked out for the holidays as well, including an enormous evergreen tree in the lobby decorated to the hilt.

Balboa Park

Meanwhile, Balboa Park in downtown San Diego puts on the steadily growing December Nights, an astounding holiday festival that draws on cultural traditions from all over the world. For four decades, December Nights has taken over the sprawling, 1,200-acre park that showcases the world-famous San Diego Zoo along with an assortment of renowned museums and gardens. But for one weekend in early December, the park is enlivened by countless holiday lights and a staggering spread of food vendors, making for an international holiday celebration and enormous food festival rolled into one. Add in some live holiday-themed performances at the Old Globe and other activities embedded in December Nights and it’s easy to see why visitors (and locals) turn up at Balboa Park in December.

Parade of Lights

As a prominent port of call, San Diego is also not exactly lacking in beautiful harbor views, which create the background for the explosion of holiday colors that come with the San Diego Bay Parade of Lights. For nearly a half-century, participants have shown off their inner creativity by decorating their boats based on the annual theme, which have ranged from “Aargh! A Pirate’s Christmas” to “A Tropical Island Christmas” (2018) in recent years. To get the best views of the roughly 80-boat parade, viewers show up early and spread out around the two embarcaderos that jut out into the harbor overlooking Coronado Island.

Anyone up for a short drive from central San Diego also has even more terrific options for the holidays. Though all the beach towns north of downtown (e.g. Pacific Beach, La Jolla, Encinitas, Del Mar) have their own holiday festivals worth checking out as well, driving a little east to Julian, California will give you a completely different experience. Sitting at the base of the Cuyamaca Mountains, Julian is known for its snow-capped mountain scenery, crisp air, and wonderful little historic area that springs to life for the holidays. Regionally famous for the pies and various homemade delicacies, Julian has a fun tree-lighting ceremony and looks like a postcard once Main Street is fully lit with holiday excitement. From major festivals celebrating diverse holiday traditions to events that take full advantage of local geographic advantages, San Diego is simply a great place to spend the holidays.

3. Williamsburg, VA

Christmas Wonderland

There’s an irrefutable holiday cheer in the air in Williamsburg, Virginia once the calendar moves past Halloween. At the heart of the action, Busch Gardens Christmas Town is a vintage winter wonderland complete with more than 10 million lights. It constantly smells of fresh Christmas trees, and has an impressive spread of boutiques lining the cozy village within Williamsburg. Unique holiday-based dining experiences, Santa sightings, and a North Pole workshop help create an electrifying atmosphere sure to get the holiday fun started in Williamsburg. Nearby, at Yankee Candle Village, Christmas is actually celebrated all year. However, it really pops to life in November and December to offer another memorable stroll through lights, decorations, and holiday activities.

Christmas Tree Lighting

Because Williamsburg is often credited with being the site of the first community Christmas tree, the tree-lighting ceremony has become a seminal way to usher in the good vibes of the season. The first tree was decorated here all the way back in the 1840s, and by 1915. Williamsburg celebrated with its first community tree complete with electric lights, making the annual ceremony a timeless tradition that continues to draw both locals and visitors. Not only do participants gather to see the lighting of the enormous evergreen tree in Market Square but everyone crowds around for a reading of “The Night Before Christmas” followed by caroling.

Though Colonial Williamsburg and the surrounding region is always great for delving into the magic of the region’s rich history, history lovers have even more options during the holiday season. A short 15-minute drive from central Williamsburg to Jamestown will let you time-travel to the Christmas traditions of the first English settlement on the continent. Whether you come for planned events and activities or simply want a great location to wander and take in a traditional holiday experience, Williamsburg is tough to beat.

Final considerations

Part of the fun of holiday travel is looking for the under-the-radar possibilities that will really tie your vacation together, making the holiday season an amazing opportunity to dive headlong into new experiences and traditions. Even in places that don’t immediately come to mind when you think of the holidays, there’s a good chance there are plenty of exciting sites and local events that will put you in the holiday spirit. With an eye on local social media pages and willingness to consider contrarian options, you’ll be well on your way to finding the right balance of cozy traditions and newfound adventures no matter where you choose to travel.

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