Weekending in Charlottesville: A Quaint Downtown With Nearby Wineries, Cideries, and More

Get schooled on the grown-up charm of this Virginia college town.

visiting charlottesville

Check out the art gallery at the Quirk hotel while visiting Charlottesville. Photograph by Betty Clicker

With plenty of posh options for lodgings, a pedestrian mall packed with shops and restaurants, and wineries, cideries and breweries down seemingly every winding country road, it’s fully possible to do an entire weekend in the home of the University of Virginia without ever stepping foot on campus grounds.

Distance from Philly: 4.5 hours

Where to Stay: Choices range from boutique-y hotels to luxe inns. You can get the best of both worlds at Quirk, an offshoot of the original Richmond property; it opened, somewhat unfortunately, at the beginning of the pandemic. Local art is the emphasis here, and you’ll find eye-catching original works in both the first-floor gallery and throughout the hotel. (Quirk even hired C’ville-born painter Kiki Slaughter to design the watercolor headboards in each room.) Indulge in the tasting menu at on-site restaurant the Pink Grouse (a lovely spot for special occasions), or make a point to grab drinks at the rooftop bar. From the mid-$200s per night.

What to Do: C’ville’s locally made libations scene just won’t quit, and the only problem you’ll have hopping from vineyard (Pippin Hill, King Family) to cidery (Castle Hill, Potter’s) to brewery (Starr Hill, Three Notch’d) is deciding on a DD. The utterly walkable downtown is dotted with cute boutiques like Eloise and Rock Paper Scissors, but it’s worth pausing for a moment of reflection on Heather Heyer Way, named in honor of the woman killed while protesting the Unite the Right rally in 2017. And if your inner history nerd just can’t resist the call of Thomas Jefferson’s Academical Village, download the “Walking Tours of Grounds” app for a guide to, among other topics, the role enslaved Americans played in building and maintaining the university.

The Eating-and-Drinking Sitch: For breakfast, do a down-home Southern brunch at Croby’s Urban Viddles, or pick up croissants and cafés au lait to go at MarieBette. Sandwiches from Take It Away or the Market at Bellair (don’t be deterred by the gas-station backdrop) make for perfect picnic lunch fare, and Lampo Neapolitan Pizzeria, Public Fish & Oyster, and James Beard-nominated Alley Light are just as good for small group dinners as for date nights.

visiting charlottesville

Pastries and coffee from MarieBette. Photograph by Carrie Coleman

Can’t-Miss List

1. Hit the Quirk gift shop
The stylish offerings include stationery, ceramics, candles and more in the hotel’s signature shade of light pink.

2. Hike to Humpback Rocks
No matter the season, the sweeping views of the Shenandoah Valley are more than worth the trek.

3. Explore Belmont
This cool neighborhood has plenty of pretty houses to ogle and the gorgeous home-goods and plant store Be Just.

Published as “Enjoy Southern Hospitality in … Charlottesville” in the “Road Trip!” guide in the March 2021 issue of Philadelphia magazine.