Here’s How To Experience The Posh Side Of Charlottesville

By Kelly Magyarics | October 19, 2021

More than a college town, this city provides posh wineries, horseback tours, and hotels for an over-the-top getaway.

With classic architecture, American history, world-class wines, and exciting new places to dine, drink, and shop, this college town more than makes the grade for a pampered sojourn.

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Keswick Hall

This posh resort recently reopened its doors after extensive renovations, delivering understated sophistication and impeccable service. Housed in a building dating back to 1912, the high-end property features reimagined rooms and suites with amenities like Duxiana mattresses, Frette sheets, and handcrafted chocolates. Outside your door, you’ll find Marigold by Jean-Georges, the resort’s local-cuisine-focused restaurant under the direction of French celebrity chef Jean-Georges Vongerichten, as well as coffee shop The Counter and Crawford’s, where you can imbibe craft cocktails and rare liquors. The property also boasts a spa, two pools, and a golf course. Rates from $995 per night. 701 Club Dr., Keswick

vineyardPhoto by Renee Sklarew

Day 1

Morning: The posh tasting room and inviting stone patio overlooking the vineyards at Early Mountain Vineyards in Madison are about as pretty as they come. Stop by on the way to Charlottesville for a glass of their Provence-meets-Albemarle rosé from talented winemaker Ben Jordan and a light lunch of cheese, charcuterie, and beet-and-ricotta hummus. Even if you’ve already visited James Monroe’s Highland, return to the estate of the fifth U.S. president for the new behind-the-scenes guided tour, which includes an outdoor overview and inside look at the current re-curation.

Afternoon: After check-in, head to The Shops at Stonefield, an outdoor lifestyle center close to the Downtown Mall. You’ll find names you know and love, like Kendra Scott, Bluemercury, and Williams Sonoma, along with upscale local boutiques like Poshabilities. There’s a movie theater, too. Flagging yet? Grab a midafternoon pick-me-up cold brew from popular local chain Grit Coffee.

Evening: For dinner, try the elegantly modern Broadcloth Restaurant located in the new Wool Factory, which also houses a cafe and brewery, all situated in a historic textile factory. Select either a four- or six-course prix fixe menu, or eight-to-ten-course chef’s tasting, with optional beverage pairing.

Day 2

Morning: You might not be thrilled to hear your alarm clock ringing before dawn, but that feeling will dissipate once you are gently soaring over the Albemarle region in a sunrise hot-air balloon ride with Monticello Country Ballooning, which includes a Champagne toast. Tuck into an early lunch at the seafood- and Southern-fare-focused restaurant The Ridley, near UVA’s campus in The Draftsman; start with Cajun oysters, followed by a lobster roll with lemon aioli.

horseback riding through vineyardPhoto courtesy Visit Charlottesville

Afternoon: Saddle up at Indian Summer Guide Service for a private guided horseback ride that stops at a local winery or brewery, or a customized backcountry ride exploring the meadows, bubbling creeks, vineyards, and orchards of the Blue Ridge. More of an adrenaline junkie? Do a tandem skydive from 14,000 feet with 60 seconds of freefall over the region at Skydive Orange.

Evening: Cap off your adventurous day with modern French cuisine at the intimate Fleurie, where the three-course tasting menu changes daily and may include options like Virginia oysters with caviar, beef carpaccio with blistered capers, or whole poached lobster with Sauternes-and-ginger sauce. Afterward, stop by cocktail bar and speakeasy Lost Saint for a flute from their impressive by-the-glass sparkling-wine menu or a Negroni riff with Malfy Gin, Cynar, and Aperol.

Day 3

Morning: You’ll want to carve out at least a few hours (or more) on your last day to explore Dairy Market, a new food hall that’s the talk of the town. Just steps away from UVA in the 1930s-era Monticello Dairy building, this exciting new venture hosts artisanal vendors and purveyors of food, beverage, agriculture, Southern culture, history, and arts, all under one roof. Get a lemon-poppyseed muffin or protein ball at Bee Conscious Baking Company, which uses ingredients, including honey, from the owners’ local farm. Pick up some gourmet ingredients and a few bottles of local wine to take home at Springhouse Sundries, or cool clothing for men and women at Quattro Tizi.

Afternoon: For lunch, nosh on panang curry, chicken satay, dumplings, and other Southeast Asian street food at Chimm Street, whose name means “taste.” And don’t miss sipping a libation at The Milkman’s Bar, a whimsical space that pays homage to 1950s soda fountains, where mixologists River Hawkins and Mike Stewart shake up coffee cocktails, bourbon egg creams, and a whole menu of inventive spirit-free sips.

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