Holiday Road Trip Guide: 14 Festive Destinations

If you’re looking for “holly and jolly” you’ve come to the right place. Here are 14 festive road-trip worthy items that we have enjoyed from various pockets of the U.S.

1.) Christmas at the Cave – Mammoth Cave, KY

Imagine taking in over a million glistening lights via horse-drawn wagon on the edge of Mammoth Cave National Park. Christmas at the Cave gives you that experience. Become immersed in a mile of Christmas sparkle guided by a Belgian two horse pulling team. They are open Thursday to Sunday from 4:30 to 9 CTS through December 28th. Tickets only available on site.

2.) Aspirations in Lights at Aspire – Clinton, TN

Aspire is one of Tennessee’s newest elevated experiences. If you’re looking for a completely over the top Christmas encounter then their Aspirations in Lights is your destination. Walk through the expansive display on an accessible trail and maybe even get met with hot chocolate halfway through. There are interactive portions and playgrounds to stop at. It’s tons of fun for the whole family. Get tickets for the experience here. Make sure you snag a reservation at The Pearl to start or end your night with too.

3.) The Biltmore – Asheville, NC

The Biltmore is America’s largest home. It comes to life in the holidays with elaborate period decor, decorated as the house once was. We’ve taken the self-guided Candlelight Christmas Evenings audio tour twice. There are so many things to see that you could never see it all. Live music happens each night during the holidays. We’ve been when cellist have been playing and a choir has been singing – it adds to the whole experience. You will want to grab reservations because they sell out quickly – we recommend going on a weeknight. We’ve done both bus transports and walked from parking onto the house grounds. If you can snag a close parking spot, it is a beautiful walk through the woods where you arrive on a hill overlooking the front of the home. Pretty great first look! There are many food options as well as a winery, shopping, and art galleries. The property is massive so we recommend acquainting yourself before you go, and even mapping out what you want to see. The estate is about 8,000 acres so be aware that it takes time to get from thing to thing. Seeing house is amazing in itself but seeing it during Christmas is over the top holiday magic.

4.) Cornish Christmas – Grass Valley, CA

In the heart of California’s Gold Country, you will find Grass Valley – home to Empire Mine, what was the state’s largest and richest gold mine. Over 75% of the mine’s employees were from Cornwall, England and the Cornish influence helped shape the town. They honor their heritage with the annual “Cornish Christmas” celebration. Each Friday night after Thanksgiving through mid-December, historic Mill Street is full of vendors and Christmas magic. Chestnuts are roasted, carols are sang, cider is served. This already picturesque somehow becomes even more enchanting.

5.) Patti’s 1880s Settlement – Grand Rivers, KY

Nearly two million lights can be admired for free at Patti’s 1880’s Settlement. This grand location is a Kentucky icon. Known for their two inch pork chop, visitors flock from all over to dine, shop, stay, and enjoy. If you want to eat, we recommend making reservations ASAP! If you just want to experience the festive sparkle, no reservation needed. You can listen to our podcast with Patti’s here.

6.) New Year’s Eve – Chicago, IL

The lure of a New Year’s Eve concert snowballed (quite literally) into a 3-day family road trip to the Windy City – Chicago, Illinois! We bundled up and watched the fireworks along the Chicago River. The fireworks show lined the river along the bridge and lit up the downtown sky for about five minutes while the crowds ushered in the new year. Fireworks intertwined with falling snowflakes was the cherry on top! Tip: Bundle up, then add a layer. It is frigid cold the closer you get to the river and our toes and cheeks froze. We selected the Blackstone Hotel, an ornate 1910 building with magnificent views of the Michigan River, for our stay. Rich in history and decorated with a nostalgic flair, you can even craft a letter on the 1908 typewriter displayed in the lobby and mail it from the front desk. We even caught a glimpse of glamorous newlyweds snapping pictures in the hotel lobby on New Year’s Eve. 

7.) Solvang, CA

The Danish-inspired town of Solvang feels like a holiday year-round. Twinkle lights, windmills, a Christmas shop, European bakeries, and wine cellars – need we say more? No matter when you go, it will be a treat but especially during the holiday season. Julefest begins November 28th and lasts until January 4th. During this time, Solvang transforms into a Danish holiday dream. We haven’t caught a trip during that time frame, but it is on our list!

8.) Snowshoe Mountain Resort – WV

If you’re looking for a luxury ski town vibe on the east side of the Mississippi, Snowshoe Mountain Ski Resort. In the mountains of West Virginia, Snowshoe offers incredible views and a robust ski village complete with dining, shopping, and lodging. It is a great place to be with family, immerse yourself in the winter season, and ring in the new year. You can get the full scoop in this journal.

9.) Sevierville, TN

Dolly’s hometown was just as you’d expect it to be – charming, quaint, and beautiful with an edge of humility. We walked the streets of the lit up downtown at night, had dinner, vintage shopped, and met up with family. It is a lovely place to spend time during the holiday season. Broader Sevierville is full of so many opportunities as well.

10.) Small-Town Christmas Parade – Horse Cave, KY

Is there anything like a small-town Christmas? Especially when the whole community gathers to celebrate. That’s what you feel at the Horse Cave Christmas Parade in Kentucky. Horse drawn carriages, homemade floats, local dance teams, retro cars, and fire trucks from all over might be spotted parading down Main Street. It is good, wholesome fun. Plus, Horse Cave has a ton of antique and vintage stores right downtown.

11.) Gaylord Opryland Resort – Nashville, TN

One of the few places on earth where you can feel completely immersed in the spirit and wonder of Christmas and the Holiday Season, Gaylord Opryland Resort from early November through the first few days of the New Year is a magical place. If you love the Holiday season or if you are trying to jump start yourself into the Spirit, you need to spend a weekend at Gaylord Opryland. From the jaw dropping lobby to throwing your balcony doors open in your room, you will know the magic of the season…and that’s just the inside. Outside the Resort, you will find a Christmas Village that will allow you the fun of tubing, ice skating, bumper cars, and carriage rides through acres of lights. It’s also where you will find the ICE show, along with hot chocolate, food trucks, and more. Oh, and the shopping, too…with a massive Christmas Store to get lost in for hours.

12.) Sequoia National Park – CA

We found a little winter wonder in Sequoia National Park. What better way to see the world’s largest trees than covered in snow? Trekking through the trails with snow softly floating down mentally transported us to Narnia. The park roads will close down if conditions get too icy but if they are safely open, we highly recommend checking it out for some snow-covered splendor. Sequoia is adjacent to Kings Canyon National Park if your time allows. Tip: California has chain requirements in the winter that will be enforced in the parks during certain conditions so check on that before going.

13.) Shelby County, KY

A touch of holiday sparkle can be found throughout Shelby County, Kentucky. From festivals to shopping and all kinds of events, Shelby shows out for Christmas. Shelbyville’s Main Street is lit up and full of small businesses to support. Kentucky’s premier shopping destination is in Simpsonville – The Outlet Shops of the Bluegrass. They have over 80 stores in an open-air environment, and plenty of holiday events of their own. If we had to recommend one thing to do in Shelby during the holidays, it would be to visit the Wakefield-Scearce Galleries. Nearly 30 thoughtfully designed Christmas trees, each reflecting the spirit of the room it adorns, it is simply spectacular.

14.) Cheekwood, Nashville, TN

Visiting Cheekwood is a brilliant way to spend a night during the holiday season. There are reindeer opportunities and lights galore all over the expansive estate. The beautiful 1930’s mansion is open for visitors and the rooms are dressed in period appropriate decor. Part of the house is also art gallery. Timed entry tickets should be reserved ASAP because they can go quick.

We hope this season is merry and bright for you – happy holidays!

Thank you Christmas at the Cave for sponsoring the Holiday Road Trip Guide!