1. Great Deals on Accommodations

Whether you're staying in a local hotel or rental property – the availability increases dramatically and rates trend lower during the colder months. Especially if you’re looking for a unique experience, like staying on the grounds of a local winery.

Places to Stay Charlottesville and Albemarle County offer visitors a wide variety of places to stay, including resorts, hotels, inns, bed and breakfasts, cabins, and vacation rentals. Learn More
Sip and Stay: Winery Lodging Learn More

2. Fewer Crowds

Colder weather means fewer people, which overall equates to more enriching experiences at local restaurants, wineries, historical sites, shops – you name it! Local business owners love connecting with winter visitors and are able to dedicate more time to providing you with the best possible experience. Plus, "cold" doesn't mean freezing in Charlottesville! In fact, the average high temperature is around 50 degrees; perfect weather for hiking, outdoor recreation, special events, or exploring the many shops and restaurants around town. When it does snow in Charlottesville and Albemarle County, it tends to be mild, light dusting that only enhances the magic of the winter season!

3. Workshops and Festive Pop-Ups

Many businesses use these colder months to get extra creative inside, conjuring up magical, unforgettable experiences for travelers! If you're a foodie at heart, sign up for a hands-on cooking class at Pippin Hill Farm & Vineyards. Want to get creative and make a homemade gift for the holidays? Book a spot at Pikasso Swig's DIY Craft Bar, where their team will help you create a one-of-a-kind masterpiece to take home. More of a mixologist? Sign up for a cocktail masterclass at The Forum Hotel!


While you're there, check out their Winter Chalet Pop-Up Bar -- a cozy, festive experience only available during the winter months. Speaking of pop-ups, you'll have to visit The Doyle Hotel's 'Elf'd Up' Pop-Up Bar! The hotel's rooftop bar is expertly decorated in wall-to-wall holiday cheer with plenty of Instagram-worthy photo opportunities and of course, Christmas-themed drink specials! Booze-free visitors will also be able to join in on the fun — they've got zero proof "Ebenezer's Elixirs" available too!

Pippin Hill Farm & Vineyards Cooking Class

Embark on an immersive culinary experience with Chef Victoria Cosner including a chef demo, wine pairings, and hands-on cooking.

Learn More

PIkasso Swig Craft Workshop

Book an appointment at their DIY craft workshop and art bar and unleash your creativity. They have dozens of projects for both children and adults and a fresh selection of food and drinks.

Learn More

Birch & Bloom Cocktail Masterclass

Join our talented bartenders as they teach you how to make three cocktails.

Learn More

Elf’d Up Holiday Pop-Up Bar

immerse yourself in our wall-to-wall holiday cheer, including Instagram-worthy photo opportunities, Christmas themed drink specials and more tacky sweaters than you’ll know what to do with. Let’s get blitzen!

Learn More

Winter Chalet Holiday Pop-Up Bar

Snowflakes, twinkling lights, and a fireplace to keep you warm.. Welcome to the Winter Chalet pop-up bar at The Forum Hotel! A cozy escape with a fondue feast and seasonal drinks.

Learn More

Blow Your Own Ornament

For over 20 years during the holiday season, Chip has invited members of the public to blow their own holiday ornaments. Many families in Charlottesville consider it an annual tradition, and return year after year.

Learn More

4. Winter Wander at Boar’s Head Resort | November 22nd – January 4th

Gather your family and friends to experience a magical outing like no other in Charlottesville! Back for its fourth year (and bigger and better than ever), this half-mile illuminated lakeside stroll reveals one whimsical theme after the next. This year's experience will include twelve unique light displays along the path, drone light shows and music/dancing on select nights, snow machines, photos with Santa, and food from local vendors, including Vision BBQ and Carpe Donuts!

5. Magic on the Mall | November 21st - January 7th

You won't want to miss this year's Magic on the Mall. This free downtown celebration brings a variety of ways to enjoy the holiday season on Charlottesville's historic pedestrian Downtown Mall, including extended holiday hours, rides on the Downtown Holiday Express (Saturdays only), a self-guided 'Elves in Cville' scavenger hunt, 'Selfies With Santa' on November 30th with the big man himself, and the can't-miss Grand Illumination celebration on December 6th from 5-8PM.

Bundle up and join us so you can experience all the winter splendor and magic free of charge!

Insider’s Guide to Winter Wander at Boar’s Head Resort Back for its fourth year, Winter Wander is a family-friendly event with plentiful illuminations, seasonal fare, and more. Learn More
Experience ​“Magic on the Mall” This Winter on Charlottesville’s Downtown Mall It's hard to believe, but the winter season is upon us! This year, Charlottesville's annual Magic on the Mall is bringing even more opportunities to embrace the holiday season with friends and family on Charlottesville's historic pedestrian Downtown Mall. Learn More

6. Cozy Wineries

Nothing says 'winter getaway vibes' like enjoying a glass of wine by a warm firepit. From heated outdoor seating and firepits to indoor wood-burning fireplaces, there's no shortage of ways to stay warm while enjoying our award-winning wine region. Here are ten of our top picks with cozy indoor or outdoor options!

In addition to wineries, there are numerous craft beverage tasting rooms throughout Charlottesville and Albemarle County with indoor seating and heated, outdoor options! There's something for everyone here, including breweries, cideries, and distilleries.

Wondering where to go? Want to visit more than one place or make a weekend of it? Connect with a local transportation service to both provide you with a safe ride and help craft the perfect itinerary! Traveling with a group is much easier (and way more fun) in the winter months, as the tasting rooms are less busy and have more availability for larger parties.

Wineries Welcome to the birthplace of American wine. Charlottesville and Albemarle County are home to more than 40 wineries along the Monticello Wine Trail, offering visitors lush views and a dynamic wine scene in the heart of Virginia. Learn More
10 Cozy, Charlottesville-Area Wineries to Visit this Winter The winter months can get chilly in the Charlottesville area, but our wineries have lots of cozy outdoor and indoor seating, such as firepits, fireplaces, and heated patios. Learn More
Craft Beverages Explore the thriving craft beverage scene in the Charlottesville area. Learn More
Wine Tours & Experiences Whether you're looking to book a private tasting, transportation to multiple wineries, or an experience that's completely unique, we have everything you need to plan the perfect wine getaway. Learn More

7. Outdoor Recreation

Hiking in Charlottesville and Albemarle County is always a fan favorite – no matter what the season. Winter is an especially sought-after time for a couple of reasons. First – no bugs! What’s better than that? Additionally, given the lack of foliage, there are much more expansive views available at our favorite parks! Hiking the same trail in a different season could mean a very different experience - take a look at our trails and outdoor routes page to discover the hike that is the best fit for you.

8. Foodie Wonderland

The Charlottesville area's food scene has long been revered by locals, visitors, and even the media! With so many cuisines, styles, and atmospheres to enjoy, you'll need more than one day to make a dent! Visit our restaurants pages to start your shortlist of must-dine locales. Be sure to peruse individual websites to view seasonal menus highlighting the best of winter’s bounty. If you want to see where your food comes from and meet the people who farmed it (and do a bit of holiday shopping), head over to the year-round Farmers Market at Ix!

Up for an adventure? Join us for Charlottesville Restaurant Week in January (dates to be announced soon!) Participating restaurants offer fixed menus at discounted prices, with many that include multiple courses. It's a great opportunity to explore the local culinary scene and enjoy affordable bites, while also supporting a good cause! $1 of each meal is donated directly to a selected charity.

9. Historical Sites & Museums

The Charlottesville area is abound with historical points of interest including Presidential homes, museums, and more! Your trip isn't complete without a stop at:

Thomas Jefferson’s Monticello

Our most well-known landmark! If you’re visiting during the holiday season, we recommend opting in for a special Evening Tour, which highlights Monticello’s Jefferson-era holiday décor and traditions. While you're there, you can even attend one of their Wreath Workshops to make your very own festive holiday wreath -- perfect for adorning your own door OR gifting!

James Monroe's Highland

Private guided tours are available during the weekends throughout the winter, and self-guided general admission tours are available daily. Highland also hosts a number of community events throughout the year, such as holiday arts-and-crafts and guided hikes!

Monticello Join a Monticello guide for a tour of the Monticello quarters, and along Mulberry Row, the industrial hub of the Monticello plantation. Guides will share stories and answer questions about the enslaved African Americans who lived and labored on this… Learn More
James Monroe’s Highland Highland, the home of James Monroe, fifth president of the United States, is adjacent to Thomas Jefferson’s Monticello in Charlottesville, Virginia. Purchased by Monroe in 1793, the property was home to the Monroe family for nearly 25 years.Highland interprets the… Learn More

Kluge-Ruhe Aboriginal Art Collection

The Kluge-Ruhe Aboriginal Art Collection of the University of Virginia is the only museum outside of Australia dedicated to the exhibition and study of Indigenous Australian art. Admission is free, with 20-to-30-minute tours led by volunteer guides available at 10:30AM and 1:30PM, but reservations are highly suggested. Fun fact: Steve Martin and Martin Short recently said Kluge-Ruhe was their favorite place to visit in Virginia! The museum is family-friendly, and service animals are permitted.


Jefferson School African American Heritage Center

Located in the historic Jefferson School City Center, the Jefferson School African American Heritage Center’s mission is to honor and preserve the rich heritage and legacy of the African American community of Charlottesville and Albemarle and to promote a greater appreciation for and understanding of the contributions of African Americans and peoples of the Diaspora. Visitors can attend one of the many programs available at the Jefferson School, tour its permanent exhibition, and learn more about its history.

Kluge Ruhe Aboriginal Art Museum The Kluge-Ruhe Aboriginal Art Collection of the University of Virginia is the only museum in the USA dedicated to Indigenous Australian art. AboutExpand your world and make fascinating connections with our world-class collection of more than 3000 artworks. We exhibit… Learn More
Jefferson School African American Heritage Center Located in Charlottesville's historic Jefferson School City Center, the Jefferson School African American Heritage Center features a permanent historical exhibit, a rotating contemporary art gallery, and a robust calendar of events, all of which combine to highlight Charlottesville's African American… Learn More

10. Arts & Culture

The lively arts scene in Charlottesville and Albemarle County provides endless entertainment for visitors and locals alike. Live music, theatre, and art exhibitions are just some of the possibilities! Discover live music almost daily at The Jefferson, The Southern Cafe & Music Hall, or a variety of restaurants and wineries. Actors bring stories to life at Live Arts, featuring multi-week runs of impactful works. The historic Paramount Theater is home to concerts, community screenings, ballet, and more. Or you can visit The Looking Glass in Ix Art Park, Virginia’s first immersive art experience!

The Jefferson Theater Located on Charlottesville’s historic Downtown Mall, The Jefferson Theater was established in 1912 as a live performance theater that played host to silent movies, vaudeville acts and a historic list of live performers, ranging from Harry Houdini to The ThreeStooges… Learn More
The Southern Café & Music Hall Located on Charlottesville’s Historic Downtown Mall, The Southern Café & Music Hall opened in 2009 in the former location of The Gravity Lounge and has been the leading club level music venue in Charlottesville since that time. The Southern Café… Learn More
Live Arts Live Arts Theater has been producing provocative, crowd-pleasing plays and musicals in downtown Charlottesville since 1990. In all these years, we have never presented the same play twice! Our mainstage season runs September through May and concludes with a three-week… Learn More
Paramount Theater The historic Paramount Theater, a Charlottesville landmark now in its 90th year, presents a wide variety of live art performances. Check their website for a calendar of upcoming events. On November 25, 1931, The Paramount Theater opened its doors as… Learn More

With so many amazing things to do, Winter just might become your favorite time to travel to Charlottesville and Albemarle County! Less traffic, fewer crowds, and savings on accommodations – what's not to love? Start planning your winter stay today by visiting our places to stay page. Want help planning your trip? Our knowledgeable travel specialists are available via phone and email! We can’t wait to see you - share your winter adventures with us on social media by using the hashtag #visitcville!

Places to Stay Charlottesville and Albemarle County offer visitors a wide variety of places to stay, including resorts, hotels, inns, bed and breakfasts, cabins, and vacation rentals. Learn More
Contact Us Contact the Charlottesville Albemarle Convention & Visitors Bureau Learn More

Related Content: