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Looking for a little Christmas magic? Here are five magical towns guaranteed to fill you with holiday cheer!

Christmas has always been a magical time of year for me and growing up in Kentucky and Colorado, part of the magic has always involved snow, tons of twinkling Christmas lights, decorating the Christmas tree, my mom’s custard and of course baking tons of Christmas cookies.

Living in Florida the past several years where the average winter temperature stays mostly above 50 degrees, snow is never an option.

And I have never been able to fully embrace Christmas lights on palm trees.

Call me crazy, but it just isn’t the same.

So, we usually end up traveling somewhere cold and snowy around the holidays so we that can fully embrace Jack Frost nipping at our nose and dressing up like Eskimos.

Any of my fellow southern residents with me?

If you are looking for the best Christmas towns in the U.S. to experience the holidays, here are five of the most magical places guaranteed to fill you with holiday cheer.

Leavenworth, Washington

magical town guaranteed holiday cheer
Magical Bavarian village in Leavenworth, WA. Photo credit: The Traveling Dragonfly

This Bavarian village in the Cascade Mountains is known for its Village of Lights: Christmastown festival every winter.

From November to February, it’s Christmas every day!

With over half a million twinkling lights decorating the town, holiday characters, carolers and a Winter Market where you can search for that perfect gift, holiday cheer is sure to fill your spirit.

There is also a Gingerbread House exhibit, a gift-wrapping station and if see him, you may even get a selfie with Santa!

Other activities available in the area include downhill skiing, Nordic skiing, snowmobiling, snowshoeing, and sledding to name just a few.

magical towns guaranteed holiday cheer, Leavenworth, WA
Leavenworth’s bavarian village lit up with holiday cheer. Photo credit: Joecho.

Where to Stay in Leavenworth

Check out the Run of the River Inn and Refuge.

Only about a mile from the town center, the inn is a home away from home with many little touches that make you feel like your wishes have come true. They even have snowshoes and bicycles for you to borrow and breakfast delivered to your room is included.

If you want to be closer to town and the action, try the Bavarian Lodge.

The lodge is in the heart of the village center and embraces Bavarian architecture to the fullest along with gorgeous views of the surrounding mountains.

A full breakfast buffet is included, and you can enjoy those crisp, winter nights from the warmth of the heated outdoor pool and hot tubs. (My favorite!)

Where to Eat

Try the Andreas Keller Restaurant for some incredible Bavarian cuisine courtesy of their German chef.

There’s also the Stein, a German beer hall with an amazing 55 different beers on tap.

magical towns guaranteed holiday cheer, leavenworth, wa
Holiday cheer found! Leavenworth, WA. Photo credit: Joecho.
Children covered at no additional cost!

Breckenridge, Colorado

magical towns guaranteed holiday cheer, breckenridge
Holiday magic happening in Breckenridge, Colorado. Photo credit: Sean Pavone

Deep in the heart of Colorado ski country is Breckenridge, a picturesque mountain town known for its downhill skiing and amazing panoramic views. 

Each winter, Breck comes alive for its annual holiday celebration.

The downtown streets are decorated with Christmas cheer and you’ll even find racing Santas!

The Race of the Santas is foot race of santa look-a-likes down the main street of town and there’s also a Christmas parade during the Ullr Fest.

Ever seen a Shot Ski?

Breckenridge is home to the Shot Ski World Record event where over 1330 people participate in drinking a shot of whiskey from one VERY long ski!  Check out the video!

When you’re not enjoying the downtown holiday magic, there’s also skiing (of course), snowshoeing, sleigh rides, snowmobiling, snowcat adventures, and dog sledding to keep you busy!

And, if you’re into ghost stories, you should check out the Ghost and Saloon tours.

magical towns guaranteed holiday cheer, Breckenridge
A winter wonderland. Breckenridge, Colorado. Photo credit: welcomia

Where to Stay

There are as many different options for accommodations as there are yummy places to eat!

From the One Ski Hill Place hotel to the Where to Eat in Breckenridge

Having visited Breckenridge many times, I am partial to the Breck Brewery & Pub.  A brew pub with great atmosphere, delicious food and tons of beers on tap to choose from, it’s a great place to unwind.

magical towns guaranteed holiday cheer, breckenridge
A street full of holiday cheer! Photo credit: SWKrullImaging

Pigeon Forge, Tennessee

magical towns guaranteed holiday cheer, Pigeon Forge
The Glockenspiel inside the lobby at the Inn at Christmas Place. Photo credit: Kathy Bobzien

If you’re looking for a tender Tennessee Christmas, look no further than Pigeon Forge.

At the Inn at Christmas Place, you can immerse yourself in holiday cheer every day of the year.

Rooms are decorated with their own Christmas tree and every evening cookies are available in the lobby.

There’s also a beautiful giant Glockenspiel in the lobby that plays Christmas carols on the hour from 9am to 9pm.

Santa and Mrs. Clause are often seen greeting guests and answering inquiries about Christmas wish lists.

magical towns guaranteed holiday cheer
How you can not find holiday cheer in a room like this? Photo credit: Kathy Bobzien

What to Do in and Around Pigeon Forge

Less than 15 minutes from the Inn is Dollywood, where Christmas magic is in full-swing during the holidays. 

The five million holiday lights help make the winter wonderland scene complete during their Winterfest celebration. 

From November to February, you can enjoy Christmas shows and carolers in addition to shopping, rides, attractions, nightly fireworks displays and even Dolly Parton’s Stampede.

Where to Eat

If you like wings, you need to try the ones at Blue Moose Burgers & Wings. Fast service and amazingly good food! Be sure to try their parmesan fries! Yummm!

Another great place is the Old Mill Pottery House Café & Grille.  Their burgers are mouth-wateringly good, especially the whiskey burger. They also make their own stone ground grain bread and their pies and cakes are delicious!

New York City, New York

magical town guaranteed holiday cheer
A Central Park carriage ride is not to be missed. Photo credit: Foto Phanatic

As much as I hate crowds and big cities, I have to admit, New York City does exude a special kind of holiday spirit. 

The store window decorations that line 5th Avenue are a creative marvel and nothing beats an evening carriage ride through Central Park with snowflakes drifting down and you’re toasty warm under the carriage blanket.

One year when we were young, our parents brought us into the city and we sat 20 rows up from the stage and watched the Rockettes perform their Christmas show.

Rockefeller Center was full of beautiful lights and the tree was breathtaking in its enormity.

There was Christmas magic in the air that night. I’ve experienced it every time I’ve returned.

You should also check out the Empire State Building for amazing views of the city lights, especially at night.

There’s also ice skating, but for the best experience try the rink at Bryant Park. If you bring your own skates, you can skate for free.

Tip: If you need to rent skates, you can get a 10% discount if you pay with a Bank of America debit or credit card. Crowds are smallest first thing in the morning, the rink opens at 8am.

Magical towns guaranteed holiday cheer
Rockefeller Center comes alive with holiday magic during Christmas.
Photo credit: Wdstock

Where to Stay in NYC

I like staying near Times Square (as long as it’s not New Year’s Eve!) the Marriott Marquis at the corner of Broadway and 45th Street is great.

We usually stay there whenever we’re in town.

You’re within walking distance of Radio City Music Hall, Rockefeller Center, Times Square, and Bryant Park.

The Marriott is also home to New York City’s only revolving rooftop restaurant and lounge, The View.

Where to Eat

I gotta tell you, there’s so many amazing places to eat in NYC that it’s impossible to narrow it down to just one or two.

If you’ve ever been there, you know what I’m talking about.

I love trying new places be it a restaurant, pub, or wine bar.

One of my favorites though are the food trucks.

I’ve had some of the absolute BEST pizza slices and ethnic foods from the street vendors…my mouth is watering now just thinking about it!

So, if you’re ever in New York, don’t pass up the food trucks…and if the line for one is around the block…don’t hesitate, just jump in. New Yorkers know their food, I promise you it will be worth the wait.

magical towns guaranteed holiday cheer, NYC
Holiday magic seen from the top of the Empire State Building.
Photo credit: Monica Garliceanu

St. Augustine, Florida

magical towns guaranteed holiday cheer st. augustine
Night of Lights at Plaza de la Constitución. Photo credit: April Johnston

Last but not least, we come to my current neck of the woods, Florida.

I know it’s not cold or snowy, and has those decorated palm trees, but it IS a magical place guaranteed to fill you with holiday cheer.

St. Augustine is a beautiful, historic town. The oldest town in the U.S. actually.

St. Augustine’s Nights of Lights is something to behold.

Millions of white twinkling lights decorate over 20 blocks of the historic downtown area from November thru January.

Tip: the best place for pictures of the lights is from the Plaza de la Constitución and the Bridge of Lions.

There are several ways to experience the holiday lights: via a trolley tour, Santa’s Red Express Tour, by boat, from the top of the St. Augustine Lighthouse and Maritime Museum, by horse drawn carriage, by a luxury golf cart and more! Read about them all here.

So many different experiences and each with its own dose of magic.

There are also boat parades, shopping, the nearby beautiful St. Augustine beach and museums to explore while you’re in town. 

If you need a tropical destination this winter, check out these 5 Stunning Warm-Weather Destinations You Need to Visit.

magical towns guaranteed holiday cheer, St. Augustine
Nights of Lights shine from St. Augustine’s Bridge of Lions. Photo credit: Sean Pavone

Where to Stay in St. Augustine

There are many beautiful and delightful places to stay near the downtown district.

My personal favorite is The Collector Luxury Inn and Gardens.

Once you’re there you’ll see why.

It’s adult only (sorry kids!) and once a private home, The Collector has been renovated and is now an inn whose atmosphere blends history and art.  It’s peaceful, unique, and everyone is very helpful and friendly.  The fire pit at night is a great touch, the perfect ending to your day.

Where to Eat

Near The Collector, is the Prohibition Kitchen.

A 1920’s themed pub, they have delicious food, great drinks, and live entertainment.

They don’t take reservations so get there early or be prepared for a wait.

Another great option if you’re in the mood for Italian (Sicilian), is Casa Benedetto’s Ristorante. It’s small, cozy, and serves the best homemade Italian food outside of Italy.

magical towns guaranteed holiday cheer, st. augustine
A little holiday magic in St. Augustine, Florida. Photo credit: Sean Pavone

So whether you’re looking to walk in a wintery wonderland, or just dreaming of a white Christmas, these five beautiful, magical towns are full of Christmas spirit and are guaranteed to fill you with holiday cheer.

Embrace your inner dragonfly and take a leap and travel somewhere you’ve never been and experience a holiday trip like none other this year.

You’ll make memories to share that will last a lifetime!

If you’re looking for gift ideas, take a look at Best Gift Ideas for the Outdoor Woman. Searching for ways to show off your travel mementos? Read 9 Inspiring Ideas for DIY Travel Mementos.