The Chiles family has been farming in Central Virginia for over 100 years—you could say that we know a thing or two about what to do in Charlottesville, Virginia. Read on for our inside guide on to how to spend the perfect ladies weekend in Charlottesville. Leave the kids and hubby at home—Momma needs some time with her girlfriends!
Friday Night: Out on the Town
From cute boutiques to entertainment venues, the Downtown Mall has it all.
Indulge in Retail Therapy
First stop: Charlottesville’s downtown pedestrian mall. Sneak in some retail therapy at the mall’s charming boutiques stocked full of gifts, accessories, and decor that you might not need but will absolutely want. We love Roxie Daisy for home décor, O’Suzannah for candles, lotions, books, and other odds n ends, and Rock Paper Scissors for the cutest stationary you’ve ever seen.
Relax with Dinner and a (Free!) Show
Anyone can appreciate the price of the next stop: free. Soak in the sun while getting your groove on at Fridays after Five, a free concert series on Charlottesville’s downtown pedestrian mall that takes place, you guessed it, every Friday after 5 PM.
For music lovers looking to start their “Cville” weekend early, visit the mountain for the Thursday Evening Sunset Series, a free event featuring live music, dinner, and wine and hard cider tastings.
After the concert, dinner on the mall is a must. For an upscale vibe with fancy food and fantastic views, opt for Commonwealth Sky Bar. If the ladies love sushi, there’s nowhere better than Ten. Looking for something more casual? Venture off the tourist path with margaritas and Texas-style tacos at Brazos Tacos in the industrial IX Art Park, located a few blocks from the downtown mall.
Saturday: Eat, Drink, Repeat
Fresh veggies are a favorite find at the Charlottesville City Market. Instagram: @CvilleCityMarkets
Start the Morning Bright and Early at the Charlottesville City Market.
It may be 8 AM but it’s never too early for tacos, especially not the authentic Mexican tacos the Charlottesville City Market dishes out. Farmer’s market purists will appreciate the locally-roasted coffee, locally-raised meats, and locally-grown flowers (sensing a theme?). But don’t fill up too early—the tastiest part of the day is still to come.
C’mon Up to Carter Mountain
Drive up the mountain for pick-your-own seasonal fruit (see our fruit availability calendar for details). Come early to beat the crowds and don’t forget your camera—the best view in town and rows of fruit trees are highly Instagram-able. After you’ve picked your fill, visit the Country Store for fresh cider donuts, sugar coma-inducing desserts, and apple cider. Claim a picnic table for the group, spread out the goodies, and dig in.
Wine lovers don’t have to go far to taste Virginia’s favorite libation; Prince Michel Vineyard and Winery has a tasting room right here on Carter Mountain. Prince Michel has been using Carter Mountain grapes to create their award-winning wines for years—talk about #drinklocal! Hard cider fans can enjoy a flight, pint, or growler of cider, fresh from the tap at Bold Rock Hard Cider Cellar.
Explore Charlottesville’s many wineries or stay up on the mountain for sweet views with your booze.
Wine and Dine
If Central Virginia had a middle name, it’d be “Incredible Wineries.” For a winery map and guide, check out the Monticello Wine Trail. Some highlights include Jefferson Vineyards, Blenheim Vineyards, and Pippin Hill—all within a 20-minute drive from the orchard. In all our years, we’ve never grown tired of the booze and views Cville offers.
If you’re not completely stuffed by the end of the day, venture into quaint downtown Belmont for dinner. The cluster of restaurants hidden within one of the city’s oldest neighborhoods lay claim to some of the best eats in town. Go family-style with sangria and tapas at Mas (consistently voted best restaurant in Cville), share an intimate rustic Italian dinner at Tavola, or go local with Virginia eats at The Local.
Sunday Morning: Walk it Off
UVA’s historic Rotunda
Get Outside for Fresh Air and Exercise
Grab a latte from local favorite Shenandoah Joe’s coffee roasters and then take an early-morning stroll through UVA’s grounds. Enjoy the Jeffersonian architecture and channel your inner founding father (no judgment if you feel the urge to break into a Hamilton number). If your hiking boots are burning a hole in your knapsack, trek out to Monticello Trail—bonus, it’s only minutes from Carter Mountain, making it easy to pop up for a Sunday morning donut and extra cider to bring home.
Brunch ‘til You Drop
Then, if there’s still room after Saturday, it’s time for what is arguably the most important component of a ladies’ weekend: brunch. In our biased opinion, the all-you-can-eat pancake breakfast at our sister orchard Chiles Peach Orchard in nearby Crozet is the best brunch option. Pancakes piled high with seasonal fruit topping is the ultimate comfort food, and when you pair them with a fresh breeze and view of the fruit trees in the valley, it’ll be hard to head home and leave ladies weekend behind.
