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Helpful Tips for Your Upcoming Charlottesville Travel This Winter

If you’re looking for a winter trip stateside, then why not consider a Charlottesville travel adventure? With the new year finally here, we’re into the dead of winter. And with the pandemic still throwing us for unexpected loops, some of us may be forced to keep our winter travel stateside this year.


If you’re in the Mid-Atlantic area and are looking for a dreamy winter wonderland to add to your must-travel list, then consider putting Charlottesville, Virginia on it. This idyllic small city is located in Central Virginia and is home to many famous places. Get your winter gear from places like, and you are all set to explore the winter in Charlottesville.


Let’s go ahead and take a look at how much fun you can have in this small town this winter season with these Charlottesville travel ideas.


Charlottesville travel


Charlottesville Travel Ideas for This Winter

Thomas Jefferson’s Monticello


First up on our list of Charlottesville travel ideas is Monticello. While Virginia is known as the “Mother of the President’s,” one of its most famous presidential locations is Charlottesville – Thomas Jefferson’s Monticello.


Jefferson gave the estate its name, “Little Mountain,” as it is nestled beautifully on a little mountain.


From the gardens, you get breathtaking views of the Blue Ridge Mountains (which surround the city of Charlottesville), and you can also see his daughter’s home – Edgehill (now a private residence) from the grounds as well.


You don’t have to be a history buff to enjoy the guided tour of this beautiful home which still holds his library collection, various artifacts, and more.


The garden grounds aren’t as spectacular in the winter, but they remain breathtaking nonetheless, which will leave you wanting to come back in the summer to see it blooming.


You can learn a lot about our nation’s history here, including the stain of slavery – it’s worth a visit.


Charlottesville travel

The Downtown Mall


Second up on our Charlottesville travel ideas is the Downtown Mall. It is the nation’s longest pedestrian mall beautifully lined with a wide brick walkway, it’s home to something for everyone.


There are plenty of local restaurants (you won’t find a chain insight) that appeal to even the strictest diets or lifestyles. Local boutiques and art galleries abound as well, so whether you’re looking to window shop or invest in that perfect piece to go above your mantel, you can find something quickly.


Noteworthy restaurants to check out are The Whiskey Jar and Petit Pois, don’t forget to grab an ice cream on your stroll from the famous Chap’s.


This cute little diner offers savory fare but is best known for its retro look and delicious ice cream. Catch up on an old episode of I Love Lucy while you enjoy homemade ice cream in a variety of flavors.


If you need a pick me up, the iconic Mudhouse coffee house is towards the end of the mall, right past Millers – the restaurant/bar that Dave Matthews worked in and got his start performing.


Charlottesville travel

The University Of Virginia

The third idea for your Charlottesville travel is the University of Virginia where you can feel the touch of the University in almost every corner of Charlottesville, but touring the campus is something else – especially during the winter.


Take a stroll down the famous “lawn,” which now houses graduate students. You can still see Edgar Allen Poe’s room set up just as it was when he lived on The Lawn.


You also must check out the gorgeous Rotunda – which Thomas Jefferson designed – and take a selfie on its iconic steps. As far as Charlottesville travel goes, this location is iconic.


The University’s main campus is located in Charlottesville, known by locals as “The Corner,” and it’s home to various bars, restaurants, bookstores, and even a few upscale boutiques. Restaurants worth checking out on the corner are the infamous White Spot and Virginia.


A little off the beaten path is Crozet Pizza At The Buddhist Biker Bar which has some of the best pizza you’ll eat in your life.


In addition to the history and delicious eats on the corner and campus of the University, you can find several charming used bookstores. If you’re a rare book collector or want to talk to some people that know a thing or two about just about any author, check out Heartwood Books – it’s a must-visit.


Charlottesville travel


Explore Wineries


The fourth of our Charlottesville travel ideas is exploring the many wineries! With 40 wineries to explore, you’re sure to find a cozy spot to sip whether it’s a special occasion or a casual one.


Thomas Jefferson actually pictured Charlottesville to be dotted with vineyards. Seems that his vision came to fruition after all. The Monticello Wine Trail has 40+ wineries, each with its own unique personality and story to share.


World-Class Accommodations


When planning your Charlottesville travel this winter it’s important to not overlook accommodations. While there are always luxurious places to stay and shop in big cities, you don’t always get the same experience in small towns.


In Charlottesville, that is not the case. With luxe shops like Scarpa and Eloise where you can put a dent in your credit cards or fabulous day spas like Neroli or The Boars Head Inn to splurge on treatments, you can expect high-end experiences all over town.


While strolling through the city, ask locals where their favorite places to go out are – the atmosphere in Charlottesville is incredibly friendly. It has been voted one of the “happiest towns” in America several times.


Charlottesville travel


Outdoor Recreation


One can’t plan Charlottesville travel without considering its breathtaking natural spaces. With trails in Charlottesville, Albemarle County, and the nearby Shenandoah National Park, there are options for just travelers with a range of abilities.


Final Thoughts


Charlottesville travel during the winter can seem daunting due to the harsh weather and flight delays, but don’t let that dampen any plans you have for exploration. It just takes a little planning and making sure you carry on your serum for sensitive skin, so you look fabulous upon arrival! Bon Voyage!

Christa Thompson

Christa Thompson is the Founder and Chief Editor of The Fairytale Traveler. She started traveling the world in 2003 when she attended a summer abroad study at the University of Cambridge in England. Since then, her wanderlust has been fierce. Her three passions in life are her son, traveling, and being creative. The Fairytale Traveler brand gives Christa the opportunity to do all of these things and to live intentionally every day. "It's never too late to believe in what you love and to pursue your dreams." -Christa Thompson

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