Best Places To Visit In Charlottesville For Holiday Cheer
I’ll admit it - I am THAT PERSON when it comes to the holidays. I start watching my favorite Christmas movies before Halloween has even happened. I listen to Christmas music in July (it’s a stress reliever!). There is nothing I love more than the most wonderful time of the year, nothing I look more forward to than the hap-happiest season of all…usually.
I’ll also admit this: I - for the first time ever - have lost my holiday spirit. I know, I know...it’s not even Thanksgiving! Honestly, it’s not great timing. I’ve decided to write this post on the best places to visit in Charlottesville, VA for holiday cheer, yet all I want to do is commiserate with Ebenezer Scrooge while decked out in my not very festive bathrobe on my couch at home. But still here I am, writing a post about holiday cheer because I am hoping by helping people find their holiday spirit, I’ll be able to find mine again.
Best Places To Visit In Charlottesville For Holiday Cheer
Luckily, Charlottesville is actually the perfect place for even the grumpiest of souls to find Christmas cheer. It’s a beautiful time of year here. Nestled in the beautiful Blue Ridge Mountains, the city goes into full holiday mode with blinking lights, garlands and holiday decorations everywhere you turn. It’s like the city’s history and charm become even more emphasized and that manages to give the town a super festive vibe, making it a truly magical time of year. Here is my roundup of the top places to visit in Charlottesville to experience the best of the season.
IX Art Park with Ollie - taking in the Downtown Decorations
The Historic Downtown Mall
The Downtown Mall is always one of the most festive spots for me during the holiday season. In addition to being busy with people shopping or gathering to celebrate, it just looks like a Christmas village (although usually one without snow). Starting right after Halloween, the storefronts are all decorated and restaurants boast festive drinks like Hot Toddy’s and Apple Cider. Plus, at the end of the historic Downtown Mall you can visit the giant tree, a surefire way to feel festive.
You can spend an entire day exploring all there is to do on the Downtown Mall, and there are aso a ton of events to celebrate the season listed later in this post.
Boar’s Head Resort
Boar’s Head Resort embraces the holiday season and even offers a ton of events, as you’ll see later on this post. As a result, it looks the part of a resort tucked away in a festive Christmas town - it’s a true winter wonderland! There are decorations all around, an abundance of events to sign up for (starting in November - Winter Wander, Breakfast with Santa, Fireworks and more), s’mores to eat and seasonal cocktails to drink. It honestly makes me feel like I’m on the set of a Hallmark movie during a winter festival and I love the feeling of escapism that produces. Check out their website to plan your visit.
The Shops at Stonefield
Located on Route 29 and near the Downtown Mall, The Shops at Stonefield serve as a great gathering spot in town for those looking to switch things up from downtown. With a ton of shops and a handful of restaurants, they go all out with decorations and events, which I’ll cover later on in this post.
The vibe is a little more suburbia than the usual Charlottesville feel, but it’s a fun spot and an easy way to get your shopping in while enjoying holiday cheer.
Dairy Market
I am a huge fan of the Dairy Market; it’s a great spot in town for people of all ages to meet up. It’s also home to one of my favorite restaurants (South & Central), a number of great food vendors (like the vegan GRN Burger), one of my favorite dog friendly breweries (Starr Hill) and one of the best stores to buy Virginia products (Brigid and Bess).
The Tree at Brigid & Bess at the Dairy Market
They also have the holiday spirit down, with decorations and events throughout the season. From visits from Santa to Family Game Night every Tuesday, I highly recommend visiting here for some festive family friendly fun. It’s a great place to spend a chilly winter night.
Carter Mountain Orchard
When I think of Christmas in small towns, I think of hot apple cider (although mine is usually of the spiked variety). There is no place better for that than Carter Mountain, and Carter Mountain at Christmastime is pure magic. With its beautiful views of the Blue Ridge Mountains and its apple orchards, it would be impossible not to get caught up in the feeling of wholesome fun here. Plus, they have a ton of great local shopping at their market, which makes for fantastic presents.
As it is an orchard first and foremost, their offerings and hours of operation do change so be sure and check their website before planning your visit.
Holidays at the Presidential Homes
Looking to revisit the ghosts of Christmas past? The Charlottesville area is home to Thomas Jefferson’s Monticello, James Monroe’s Highland, and James Madison’s Montpelier. All three are interesting to visit in order to gain insight into the area’s history, and all three offer holiday events.
From holiday evening tours at Monticello to Highland for the Holidays, it’s interesting to see what it would have been like to celebrate the holidays back in the day. Check out their sites for any open house events and see for yourself!
Get Directions to Monticello
Get Directions to Highland
Get Directions to Montpelier
Wineries
Doesn’t drinking wine by a fire feel like Christmas to you? There are so many great wineries where you can spend an afternoon doing just that. Some of my favorites for holiday cheer are Veritas Vineyard & Winery and Eastwood Farm & Winery. Both have holiday events planned so be sure and check them out below, but they are all also just lovely for enjoying wine in cozy sweaters.
Get Directions to Veritas
Get Directions to Eastwood
The Clifton
Festive decor, a Michelin-starred chef and a gorgeous setting all make the Clifton Inn a great option for holiday cheer. Gather up some friends and have a celebratory evening over good food and you’ll find yourself overcome with holiday spirit. They fill up fast, so be sure and make a reservation on their site.
Charlottesville City Market
The Charlottesville City Market runs in some variation year round (with an indoor version during the coldest months) but the most festive is the Holiday Market. Open on Saturdays from November 26 - December 17 from 8:00 AM - 1:00 PM, it’s the perfect place to get in the spirit. Grab some hot cocoa and stroll around the market for great gifts for those on your list. With so many local vendors to choose from, you’ll be sure to find lots of items with which to delight.
Charlottesville Breweries
I am a sucker for seasonal beers and the local craft beer scene is perfect for that. Plus, so many of the breweries get into the holiday spirit, making them a perfect stop for holiday cheer while enjoying a pint. Try Snow Blind at Starr Hill or Santa’s Cookies from Champion or check out the offerings at Pro Re Nata (located in Crozet, just shy of 20 miles from downtown Charlottesville) in the events below.
Get Directions to Starr Hill
Get Directions to Champion
Get Directions to Pro Re Nata
Okay, okay…I think this is starting to help my holiday cheer a bit. I’m guessing the only thing I need to do now is start attending some festive events….
Holiday Events in Charlottesville
As you can see, Charlottesville gets into the Christmas spirit. Therefore, it’s no surprise there are a number of great events for you to experience holiday cheer. From twinkling lights to Santa Fun Runs, there is something to suit every type of celebratory niche. Here are some of my favorites:
Charlottesville Grand Illumination
I’ll admit it - the tree on the historic Downtown Mall is extra special to me because it’s where my husband proposed. As a result, I always look forward to seeing the tree and the Charlottesville Grand Illumination is the best way to see it.
The Tree on the Downtown Mall - with Ollie as a little puppy!
For this tree lighting event, you can expect Holiday Market vendors providing food and beverages, as well as holiday crafts. Plus - the Charlottesville Ale Trail will be there with local craft beers and wine! With all of the music, food, drinks, games and more, there is plenty to put everyone in a festive mood. The best part about it? Admission is free and parking is complimentary at both the Market Street and Water Street garages from 5:00 - 9:00 PM.
Date: Friday, December 2, 2022
Time: 5:00 - 8:00 PM
Location: Ting Pavilion
Lighting of the Lawn
The first Lighting of the Lawn ceremony at the University of Virginia took place in December of 2001 in the wake of the September 11th attacks. It was intended to give a feeling of inclusion and unity during a challenging time. The tradition has continued, and with each passing year has meant something a little different, though the message is always the same: it’s a time for community to come together in a positive way and to find joy in that togetherness.
Taking place on the South Lawn at UVA, this event is open to the entire community and includes music and celebrations. Due to the amount of people needing to get through security for this event, it’s best to arrive about 45 minutes early and be sure to check on their site for what items are prohibited to bring.
Date: Thursday, December 1, 2022
Time: 7:00 - 9:00 PM
Location: South Lawn at UVA
Winter Wander at Boar’s Head Resort
Presented by the University of Virginia, the Winter Wander at Boar’s Head Resort is the best way to feel the Christmas spirit while getting lost in nature. You’ll experience the best light display in Charlottesville while on a magical lakeside stroll.
After your stroll, be sure and check out the holiday vendors at the market or grab snacks and a seasonal cocktail before settling down on the cozy patio equipped with fire pits.
Be sure and look on their site to purchase tickets, as well as see what special entertainment will coincide with your visit. From Santa to Fireworks, there are a couple of fun options. If you want to add dinner into the mix, be sure and make reservations and don’t forget - there’s even an overnight package to look into!
Date: Select Nights: November 18, 2022 - January 7, 2023
Time: 30 minute blocks from 4:30 - 8:30 PM (Tickets required, dependent upon availability)
Location: Boar’s Head Resort
Veritas Illuminated @ Veritas Vineyard & Winery
Veritas is one of my favorite wineries in the area and I’ve always loved going there around the holidays because they have a fireplace and a giant tree - what could be better? This year they have decided to take their holiday spirit to the next level with Veritas Illuminated.
A 1/4 mile walking path, you’ll be able to stroll through the illuminated woods and among the vines for a very special light display experience. Get lost in the holiday magic and then celebrate with delicious wine! Tickets are $15/adult and $10/child so be sure and reserve ahead of time.
Date: Select Evenings: November 17, 2022 - January 8, 2023
Time: Timed entry from 5:15 PM - 8:30 PM (Tickets required, dependent upon availability)
Location: Veritas Vineyard & Winery
The Tinsel Trail Illumination and Sip & Shop at Stonefield
During COVID the Junior League of Charlottesville came up with a great way to celebrate the season with the Tinsel Trail. This year it will consist of 100 live Christmas trees sponsored and decorated by local businesses, organizations, families, groups and individuals. The idea is to bring holiday cheer to the community while raising money to benefit the Junior League, a nonprofit volunteer organization.
During the illumination ceremony on November 26, Stonefield will also be hosting a Sip & Shop event. You’ll be able to walk around the participating shops at Stonefield while enjoying an adult beverage from one of the participating restaurants (Burger Bach, Burton’s Bar & Grill, Matchbox, and Torchy’s).
Date: Saturday, November 26, 2022
Time: 5:00 - 7:00 PM
Location: The Shops at Stonefield
Pro Re Nata Holiday Market
Pro Re Nata Brewery is always a fun spot to visit, as they have a ton of outdoor seating and there is usually plenty of music and entertainment. It is also a perfect spot to have a holiday market and this one gets pretty large.
With over 30 vendors expected, you’ll be able to partake in live music, photo stations, local artisans and even see Crozet’s original Santa! You don’t have to sign up to attend, just show up and enjoy a beer while you take in the festivities.
Date: Saturday, December 3 - Sunday, December 4, 2022
Time: 11:00 AM -6:00 PM
Location: Pro Re Nata Brewery
Holly Days
Looking for a holiday event for the family? Look no further than the Annual Family Winter Festival at James Monroe Highland and hosted by the Discovery Museum. This event includes crafts, activities and stories. Enjoy making ornaments and candle dipping while sipping on hot apple cider and eating donuts.
In addition to being in a beautiful historic setting, this event also raises money to support Virginia Discovery Museum, making it holiday cheer with a cause. Before November 30th, tickets are $18. Walkins are welcome depended on availability and tickets the day of are $20/person. Purchase your tickets ahead of time here.
Date: Saturday, December 3, 2022
Time: 10:00 AM -12:00 PM
Location: James Monroe Highland
Breakfast with Santa
I personally love breakfast, and if you can make it with Santa it becomes a thousand times better. One of the many holiday events offered by Boar’s Head Resort, Breakfast with Santa is extra special. While it’s not a Santa pancake breakfast per se, you can still enjoy a delicious breakfast as a family (view menu here); your little ones also get to meet Santa, have their picture taken and enjoy a historic carriage ride.
Reservations are required. Breakfast with Santa is $40/adults, $20/children ages 6-12 and is free of charge for children five and under.
Date: Saturdays & Sundays, November 26 - December 18, 2022
Time: 9:00 - 11:00 AM
Location: Boar’s Head Resort
Barracks Road Parade
Who doesn’t love a parade? With colorful floats and an appearance from Santa, the parade at Barrack’s Road Shopping Center is a great way to kick off the holiday season. Plus, what a perfect spot to get in some of your holiday shopping!
Date: Saturday, December 3, 2022
Time: 9:30 AM
Location: Barracks Road Shopping Center
Wreath Making at Eastwood Farm and Winery
Eastwood Farm and Winery is one of my favorite wineries. It’s only six miles outside of town (extremely close for a winery) and in addition to their wine, they also have beer, seasonal drinks (like mulled wine) and good food. The setting is also gorgeous and so it’s the perfect spot for a Wreath Making event.
The frames, locally sources evergreens, cones, pods, wires and instructions are included. For the decorations and ribbon, feel free to bring your own items. They’ll have staff to help you design your wreath and - if you provide the ribbon - the staff can make a bow at no additional charge. Tickets are $55.00.
Date: Wednesday, December 7, 2022
Time: 4:00 - 7:00 PM
Location: Eastwood Farm and Winery
The Nutcracker at the Paramount Theater
What screams Christmas more than watching the Nutcracker? Gather up the family and head to the historic Paramount Theater to watch stars of the Ukraine Ballet as they perform this holiday classic. With two showings available on Sunday, November 20, you’ll be able to make a day (or a night) of it by grabbing food at one of the many wonderful restaurants on the historic Downtown Mall.
Date: Sunday, November 20, 2022
Time: 1:00 PM & 5:00 PM
Location: The Paramount Theater
Trans-Siberian Orchestra - The Ghosts of Christmas Eve
Would you like some rock with your holiday spirit? The Trans-Siberian Orchestra will be back in Charlottesville with the return of The Ghosts of Christmas Eve: The Best of TSO. It is sure to be a fantastic performance.
Date: Thursday, December 15, 2022
Time: 7:00 PM
Location: John Paul Jones Arena
Santa Fun Run/Walk
Want to get in the festive spirit while participating in a good cause? Benefiting the Arc of the Piedmont, a group with the mission to help serve people with intellectual and developmental disabilities, this event is also offering up some friendly (optional) competition. Fundraise beforehand to help this great cause and then, on the day of, don your Santa hats and elf ears for a 1 mile run (or walk) in Downtown Charlottesville.
Enjoy lite snacks at 9:00 AM before the race begins at 11:00. Have fun running for a great cause! The cost to participate is $25/adults, $15/children 3 - 12 years, and children under 3 get in free.
Date: Saturday, December 3, 2022
Time: Registration & lite snacks start at 9:00 AM; Race goes from 11:00 AM - 12:00 PM
Location: Downtown Mall in front of Ting Pavilion
6th Annual Brew & Buddy Run and Elf at the Paramount Theater
I participated in the Brew & Buddy Run back in 2019 and it was a ton of fun. Starting off at the Paramount Theater, you will run to two different breweries in town (Champion & Three Notch’d), where you will receive a free pour at each. From there, you’ll run back to the Paramount to enjoy a showing of Elf (and $1.00 off a beer purchase at the theater).
Tickets for the movie and the run are $25/person and I suggest getting them early (you do have the option of only purchasing the movie ticket as well). You will also need to sign a waiver before you receive your wristband.
Annual Brew & Buddy Run with one of my favorite people, my friend Katie
The more festive you are, the more fun you will have so get decked out in your finest Elf gear…and a word to the wise from someone who has been there: running with a stomach full of beer is harder than you think so definitely avoid chugging and maybe consider hydrating a bunch beforehand.
Date: Saturday, December 11, 2022
Time: 4:20 PM for the run; 6:15 PM for the movie
Location: The Paramount Theater
There you have it - my holiday cheer has been restored! I’m so excited to take in all that Charlottesville has to offer in order to feel festive this holiday season. Hopefully I’ll see you around at one of these events!
In the meantime, cheers and happy celebrating!
