A Winter Getaway in Charlottesville, Virginia

You might think of Spring or Fall as the best time to head to Charlottesville, Virginia. Sure in this part of Central Virginia, lolling on a vineyard patio, lingering at a center patio on the Downtown Mall, or even maybe some hiking (Not for me! Haha!) might come to mind. However, there is a certain charm to Charlottesville winter getaways. Hotel rates are cheaper. Vineyards are less crowded. It’s easy to get into a restaurant of your choosing.


Everything to do on a winter getaway in Charlottesville,, Virginia


I recently enjoyed a Sunday-Monday Charlottesville vacation. While we had to plan a bit to find spots that were open each day and we had a fantastic time. You’ve still got a month or so before the official first day of Spring and a little longer before those perfect spring temperatures kick in. So take advantage of a winter Charlottesville weekend. Here’s how to do it right.

Where to Stay in Charlottesville

On this trip, I stayed at the Graduate Charlottesville. It’s located right on The Corner near the University of Virginia. If you can snag a winter rate, the location is perfect. There are plenty of restaurants, bars and shops right outside and you can easily walk or drive to the Downtown Mall. Because of the proximity to the University of Virginia, a lot of students use the lobby and “game room” to study, making for a young atmosphere.

If you’re looking for something more romantic and don’t mind being a littler farther off the beaten path, stay at The Clifton Inn. I wrote an entire post professing my love for this hotel. From the antique room décor to the Madeira before bed, it’s a great experience.

If you want to be right on the Downtown Mall, The Omni Charlottesville is a classic favorite. It’s classic Omni quality and provides a prime location to go just about anywhere.

Sunday in Charlottesville: Cider, Wine, Bourbon

Since some of the area wineries are closed on Mondays, make Sunday your day to explore some of the various beverage producers on the outskirts of Charlottesville.


The View from Ragged Branch Distillery is beautiful
Even in cold weather, Ragged Branch Distillery offers beautiful views.

11 a.m.: Albemarle Ciderworks

Hit the road around 10 a.m. and start your day at Albermarle CiderWorks. Albemarle specializes in ciders made from tree fruits that are becoming increasingly rare. The atmosphere is simple with a spacious tasting bar and lots of tables for relaxing. You can grab a board game to play and if you want a snack, there are cheeses and crackers to purchase, but I’d suggest saving your appetite for later in the day.

Go for a full flight and taste the range that Albemarle produces. We split two flights between our group of four. Of course, I enjoyed the Brut D’Albemarle, a dry champagne-style cider produced from Pippin apples. I also enjoyed the GoldRush that was tart and dry with citrus undertones.

 12:30: Lunch at Pippin Hill Farm & Vineyards

Winter is the time to visit Pippin Hill. This vineyard combines wine, a beautiful view and chef-crafted food year-round and on nice days it’s almost impossible to snag a table. On our Sunday afternoon winter visit, we were able to walk in and grab a table in the main dining room. If you visit Pippin Hill in the fall or winter, you can order pizzas from the delicious wood-fired pizza oven. It is only turned on in late Fall through early spring, because when temperatures heat up, the oven makes the tasting room too toasty.


Stop by Pippin Hill Farm & Vineyards in Fall and Winter for amazing pizza
Pizza at Pippin Hill Farm & Vineyards is only available in Fall and Winter.

The rest of the food menu changes seasonally, but you can never go wrong with the PHF Board, which comes with two meats, two cheeses, and tasty olive, jams and mustard. On our most recent visit, everyone also loved the sous vide deviled eggs with dried chorizo and scallions.

Head to the tasting bar before or after your meal to taste some of Pippin Hill’s wines. You can choose between a regular and reserve tasting. I tend to like wines with dry profiles, so I usually lean toward the reserve option.


Pippin Hill in Charlottesville offers a seasonal menu of delicious cuisine
Chroizo deviled eggs from Pippin Hill Farm & Vineyards.

Another reason to visit Pippin Hill on winter Sundays is Hot Chocolate and Sunday S’mores. Every Sunday through the end of March, the vineyard offers free hot chocolate and s’mores fixings next to the fire pit. There is also live music every Sunday, which adds to the atmosphere.

3:30 Bourbon at Ragged Branch

Finish your little loop at Ragged Branch Distillery. This distillery opened in 2010 and is just minutes from Pippin Hill. Hours are Thursday through Sunday from 12 to 6 p.m., making it open later than most of the wineries in the area, so it’s a perfect last stop.

The tasting room offers sweeping views of the countryside and the distillery where the Ragged Branch bourbons are made. For $9 you can sample three bourbons, all made on-site with locally sourced ingredients. For $12 you can get a cocktail. All the bourbons are well-balanced and smooth—it just depends on your flavor profile preference.


Stop by Ragged Branch to taste whiskey and sample cocktails made with it.
Ragged Branch Distillery offers several bourbons to sample.


If you are still hungry at Ragged Branch, you can also grab a burger made from the distillery’s Bourbon Beef. At any given time, Ragged Branch keeps 50 to 100 cattle that are fed the residual mash from the distillation process. The mash-fed beef is also available for purchase to take home.

7 p.m. Craft Cocktails in the Basement

Yes, Charlottesville has a speakeasy. Head to Tavern & Grocery and tell the host you’d like to head downstairs to Lost Saint. The basement bar houses an entirely different craft cocktail menu from the upstairs restaurant and a tasty snack selection. On my visit, the entire cocktail menu was inspired by Alice in Wonderland. The menu was beautifully hand-drawn with down-the-rabbit-hole inspired imagery as well. It changes regularly, so there will probably be a new theme when you visit. Not to be missed on the snack menu are the crispy marinated olives that are fried, briny, flavorful, and served with a side of dill sauce.

8:30 Late Dinner at The Alley Light

The Alley Light is another spot that is packed during peak season, but on a Sunday winter evening, we were able to walk in and choose between the bar or a table with no wait. This spot is located on the Downtown Mall, but on a side street. To find it, walk down 2nd Street and look for the hanging lamp on your left side. Then, walk down the alley and look for the door.


The Alley Light in Charlottesville offers handcrafted cocktails and gourmet cuisine
The Alley Light boasts an impressive bar and handcrafted cocktails.


Inside, you’ll walk up a flight of stairs and find a warm, speakeasy-inspired restaurant with an impressive bar. Make sure you check the chalkboard for specials. On my most recent visit, the lamb carpaccio was as beautiful as it was tasty. We also enjoyed the pork rillettes and bone marrow. Cocktails are also a necessity at the Alley Light and the menu features a combination of classics and original creations.


The flavors in The Alley Light's lamb carpaccio are delicate and delicious
Lamb carpaccio from The Alley Light.

Monday: Wander the Downtown Mall & More Tasting in Charlottesville

10 a.m. Coffee and Shopping

After Sunday’s excursions, Monday might not exactly be an early day. We opted to grab some lattes at The Graduate Hotel, then wander to the Downtown Mall. This eight-block stretch is packed with shops and restaurants and always feels like a must-do when I’m in Charlottesville. I love to spend a couple of hours browsing, even during cooler seasons. Some of my favorite shops include:

Caspari: This is the flagship store for the brand of stationery, gift wrap, paper plates, and desk accessories, but the spacious shop is filled with other gifts and apparel. Every time I go in, I find something I need. Most recently, I picked up a book on infusing liquor.

Darling Boutique: A combination of consignment and local art makes Darling one of the Downtown Mall’s more fun places to browse. While the shop has repeatedly been awarded for its consignment selections, I loved handcrafted goodies that ranged from art and jewelry to bath and body. I brought home an adorable print to hang in my closet.

O’Suzannah: The selection of cups, cards, jewelry, candles, accessories, and other fun stuff in this shop kept me and my boyfriend browsing for a while. I liked the woven seed bead earrings. He liked the mugs with statues of sea creatures and dinosaurs in the center of each mug.

Roxie Daisy: Named for the owner’s husband’s grandmother, this shop is stocked to offer a respite from the day-to-day. I love the way the shop’s boho-luxe vibe as well as the inventory of home furnishings and dining ware are supplemented by luxury bath goods, fun cards, and gifts.

12 p.m.: Lunch at Brasserie Saison

All that wandering requires a stop for a snack. Brasserie Saison is a restaurant and brewery that combines Saison, Farmhouse, and Bier de Garde style beers with Dutch- and Belgian-inspired cuisine. Don’t like beer? Don’t worry. The selection of wine and cocktails is also impressive.


Brasserie Saison in Charlottesville offers gourmet food, cocktails, beer, and wine
Brasserie Saison is a combination brewery and restaurant that also offers a well curated wine selection and flavorful cocktails.


We were in the mood for some hearty cuisine and started with braised beef bitterballen. Bitterballen are little bits of fried meat that are generally served alongside beer in Belgium. Brasserie Saison’s version was hot, crispy, and tender in the middle. The accompanying horseradish cream provided the perfect zip of spice. We also split a raclette sandwich and a Seven Hills Farm cheeseburger—both were expertly prepared, making it impossible to choose a favorite.

2 p.m. Sweet Snack

If all the walking puts you in the mood for a sweet treat, stop into Splendora’s Gelato where you can choose from between 24 and 36 flavors daily. Traditional options like Pistachio and Chocolate are present as well as more inventive creations like black sesame and chipotle cherry. I fell in love with the cardamom.

3 p.m.: Discover Spirit Lab

Spirit Lab Distilling is definitely off the beaten path. If you don’t look carefully for the big red door and little wooden sign, you just may miss it.


Spiriti Lab Distilling is Charlottesville's first distillery within city limits
Look for the red door to find Spirit Lab Distilling.


However, tasting at Charlottesville’s first legal distillery in the city limits is a unique experience. The tasting room is the production facility. So when you stop in, Ivar Aass may be hand-printing labels for his bottles, producing liquor, or packaging products to go out the door. Your $10 gets you whatever is available on that particular day. The Old Tom Gin, Single Malt Whiskey, and seasonal amaros are all not to be missed.


Spirit Labs Distilling makes an array of liquors including Charli, an aperitivo similar to Campari.
Charli is a bitter aperitivo similar to Campari made with crushed cochineal beetles as a coloring agent.

4 p.m. City Wine Tasting

Wineworks Extended is the second Michael Shaps tasting room that is located in his warehouse in Charlottesville. Shaps trained in France, then came to Virginia where he has partnered with or worked at many of the region’s most popular vineyards. At his tasting room, you can purchase flights of his high-end wines, wines from the vineyard he owns in Burgundy, France, as well as his collection of everyday drinking wines.


WIneworks Extended offers flights of Michael Shaps wine in Charlottesville
Wineworks Extended offers wine flights of Michael Shaps wines.


You can also purchase other French wines in the style he prefers. I particularly enjoyed the Michael Shaps Viognier and loved seeing locals stopping in to purchase growlers of the Wineworks Viognier. What a cool concept!

7 p.m. Campy Cocktails

Before dinner, pop in The Graduate Hotel’s Camp Ten Four rooftop bar. No, you won’t be heading outside, but you can still enjoy the fun campy décor and the city views through the windows. Try a “boozed capri” cocktail that’s served in a bag. I loved the well-balanced Bug Juice made with rum, hibiscus tea, ginger liqueur, and lime.

8 p.m. Tapas Time

Little Star is a new restaurant from Ryan Collins who spent over a decade working with Jose Andres before moving to Charlottesville to run the kitchen at Early Mountain Vineyards. The menu combines inspiration from Mexican and Spanish cuisine, with many meat dishes cooked over a hearth. Start your meal with the Jamon Iberico and the Lomo Iberico—these different hams are sliced-to-order and feature the savory, meaty flavors only found in pigs who are specially fed on black acorns in Spain and Portugal.

We also enjoyed the charred shishitos with a zippy romesco sauce and the braised lamb that was served topped with delicious greens and fresh citrus. For dessert, the chocolate cake with hazelnut ice cream and brittle was wonderfully satisfying.


Dessert from Little Star new restaurant in Charlottesville, VA
Don’t miss dessert at Little Star.


Tuesday: Provisions and the Road Home

10 a.m.: Coffee and Gourmet Goods

You can’t head home from Charlottesville without stopping by Feast! This combination sandwich shop, gourmet grocery store and caterer also has a little coffee truck inside Main Street Market with delicious coffee specialties featuring house-made syrups. After the gelato, I was clearly on a kick and went for a latte with honey cardamom syrup, which was just the right amount of sweet. My companion went for Chai Spice, which was also deliciously spicy and balanced.


Stop by Feast! for a latte flavored with a homemade syrup
Try a honey cardamom latte at Feast!


Next, we browsed the store portion of Feast!, which has an impressive selection of local and national wines, cheeses, meats, snacks, and condiments. We grabbed a bottle of Lightwell Survey Los Idiots Red Blend. Lightwell Survey is a small producer that’s dedicated to producing wines from Virginia’s lesser known vineyard locations and encouraging younger, more creative producers to succeed.

While at Feast! you should also pick up some Jam According to Daniel. This locally made, low sugar, pectin-free jam is probably the best jam I’ve ever had and I buy it obsessively every time I’m in Charlottesville. My favorite flavors are strawberry + rhubarb and red raspberry + rhubarb, but they are all absolutely delicious.

11 a.m.: Pastries for the road

Also in the Main Street Market shopping center is Albermarle Baking Company, one of Charlottesville’s best bakeries. Everything there is delightful, but I gravitate toward the fine pastries, such as mini mango mousse cakes, chocolate praline crunch cake, and cardamom cream puffs with honey-toasted pistachios (just can’t get enough cardamom). No cooler? No worries in cold weather! Another point for a winter trip.


Albemarle Baking Company is one of the best bakeries in Charlottesville, Virginia
Baked goods to go from Albemarle Baking Company.

11:30: One More Meal

Before you make that drive back to RVA, why not grab one more bite to eat? Tilman’s Cheese and Wine Bar is the perfect, quick stop. The café boasts a large menu of cheese boards, small plates, salads and sandwiches. Our favorites were the Enoteca, a classic cheese board combination of prosciutto, Taleggio, Pecorino Toscano and Castelvetrano olives, as well as the brie, fig and speck crostini. I also tried a Cricket Ball cocktail. The refreshing, aromatic blend of prosecco, Lillet Rouge, a sugar cube, Peychaud’s and rhubarb bitters was a perfectly light lunch libation.


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