Charlottesville Holiday Fun
As the holiday season officially kicks off, families and loved ones start gathering for those treasured moments we look forward to all year.
As the holiday season officially kicks off, families and loved ones start gathering for those treasured moments we look forward to all year. And honestly, there’s no better backdrop for making those memories than our local wineries. This time of year, they pull out all the stops; think cozy classes by the fire, festive makers’ markets, and yes, even surprise visits from Santa himself. Charlottesville truly comes alive in winter, and the wineries shine with their own kind of magic. Here’s a little sneak peek at some of our favorite happenings this season:
November 24 – January 3: Veritas Illuminated at Veritas Winery
An absolute staple for my family every year, Veritas Illuminated transforms the winery’s woods and vineyard paths into a sparkling winter wonderland. Picture winding trails glowing with thousands of twinkling lights, soft music drifting through the trees, and that magical hush that only winter nights seem to have. It’s the kind of experience that feels both whimsical and peaceful; perfect for families, date nights, or anyone looking to soak up a little holiday magic.
Before you head out on your stroll, grab a glass of your favorite Veritas wine and something warm and comforting from their café menu. Then take your time wandering through the breathtaking displays, snapping photos, and enjoying the gorgeous scenery at your own pace. Veritas Illuminated is open on select dates throughout the season, and we make it a point to go every year. It’s one of those traditions that never loses its charm.
December 5 and 20: Cookies with Santa at the Tasting Room & Taphouse at Mount Ida Reserve
If there’s one holiday tradition that delivers pure joy for every age, it’s Cookies with Santa at Mount Ida. This charming evening is truly for the whole family. Parents can kick back with a glass of Mount Ida’s polished estate wine while the kids enjoy a cozy, kid-friendly dinner. Meanwhile, Santa himself wanders from table to table, greeting little ones, waving, laughing, and sprinkling that unmistakable holiday magic everywhere he goes.
And just when you think the evening can’t get any sweeter, everyone gathers around the grand stone fireplace for story time with Santa; a heart-melting moment that feels straight out of a classic Christmas movie. With two dates to choose from this year, be sure to grab your tickets early…because this warm and wonderfully festive night always sells out.
December 6: Port Through the Ages at Horton Vineyards
If there’s ever a perfect season for port-style wines, it’s the holidays. Those chilly winter evenings practically beg for something rich, cozy, and slow-sipping. And Horton Vineyards is rolling out the red carpet for port lovers (and the port-curious!) with an incredible tasting straight from their extensive library collection.
You’ll have the chance to explore decades of craftsmanship, including a rare pour of their oldest vintage: 1995. It’s not every day you get to taste a wine that’s been aging longer than some have been legal to drink! Even better, the event takes place in their cellar warehouse, offering a fun behind-the-scenes peek at where the magic happens.
Just a heads-up: the cellar stays nice and cool, so bundle up… or let the port do the warming for you. Either way, this is one winter wine experience you won’t want to miss.
December 13: Hand the Light Candle Making Workshop at Merrie Mill Farm & Vineyard
If you’re hoping to gift something a little more heartfelt and handmade this year, Merrie Mill has you covered. Their Hand the Light candle-making workshop is the perfect way to spend an afternoon getting creative, and maybe even checking a few people off your holiday list. You’ll craft your very own pair of soy candles from start to finish, with all materials thoughtfully provided.
Even better, the class offers a gorgeous array of fragrances to choose from, so you can mix, match, and design candles that feel uniquely “you.” Sip on a glass of wine, settle into their whimsical space, and enjoy a slow, cozy afternoon of creating something truly special. It’s the kind of seasonal activity that leaves you with both a beautiful gift and a warm memory.
December 13: Dash Through the Hills 5K at Hardware Hills Vineyard
If your family loves lacing up for a festive 5K, especially one that gives back, Hardware Hills Vineyard has the perfect holiday outing. They’re hosting their very first “Dash Through the Hills” fun run and walk, and it’s shaping up to be a cheerful, high-energy morning for all ages. Whether you’re a seasoned runner or more of a leisurely stroller, everyone is welcome to take in the scenic views of the vineyard as they make their way through the course.
And because Hardware Hills knows how to throw a good event, the finish line celebration will be packed with food trucks, live music, and of course, their signature wines waiting for you. What makes it even better? This run supports the Monticello Area Community Action Agency, helping provide meals for families in need during the colder months. It’s a wonderful way to get moving, soak up the holiday spirit, and make a meaningful impact in our community, all before your first glass of wine.
December 19: Classic Holiday Carols at Eastwood Farm Winery
If you’re looking to wrap yourself in a little extra holiday cheer this season, Eastwood has just the thing. Spend an evening surrounded by twinkling lights, festive décor, and the timeless sound of classic carols performed by local musician Sue Harlow. It’s the kind of night that feels like stepping straight into a Hallmark scene, only with much better wine.
And speaking of treats, Eastwood has brought back their crowd-pleasing holiday milk-and-cookie flights, which are just as fun for adults as they are for the kids. Pair that with one of their signature s’mores kits and a warm mug of mulled wine, and you’ve got yourself a perfectly cozy winter evening.
December 20: Last-Minute Gift Market at Montifalco Vineyards
If you’ve found yourself procrastinating on holiday shopping (no judgment, we’ve all been there), Montifalco Vineyards is swooping in with the perfect solution. After a well-deserved break in France from November 29 to December 14, the owners will return refreshed, inspired, and ready to host a delightful last-minute holiday market.
This pop-up event is a dream for anyone who loves French-influenced wines, or just wants to give gifts that feel a little extra special. In addition to their elegant Montifalco wine selection, they’ll be offering a limited assortment of carefully curated French bottles they’re bringing back straight from their travels. Think exclusive vineyard finds you won’t spot anywhere else in the area.
And because they always go the extra mile, expect an array of one-of-a-kind, handcrafted French goodies. These beautiful, unique items will make perfect stocking stuffers, hostess gifts, or “one for them, one for me” treats. If you’re still hunting for thoughtful gifts (or just want an excuse to enjoy a glass of wine while you shop), this festive market is absolutely worth the visit.
So if you’re searching for something fun to do with the whole family over these next chilly weeks, look no further than our own backyard. This is such a magical time to get out, explore, and soak up everything our local wineries are pouring into the season, quite literally. From festive workshops and carol-filled evenings to markets, light displays, and cozy fireside moments, there’s truly something for everyone.
Bundle up, shop local, drink local, and show some love to the wineries that make our region so special. They’re hosting some truly wonderful seasonal events, and there’s no better way to celebrate the holidays than by supporting the community that supports us all year long.