Charlottesville may be best known for playing home to the University of Virginia and former presidents James Monroe and Thomas Jefferson. But these days, it’s the town’s boutique inns, artisan restaurants, and lush vineyards that make it the perfect spot for a weekend escape.

Nowhere is Charlottesville’s modern appeal more evident than at the new eighty-room Quirk Hotel, an airy and art-centric space with a firstfloor gallery and custom art in each room. Start your day with freshly baked pastries at its Quirk Café and end it with sweeping sunset views from its rooftop craft cocktail bar.

And you won’t have to go far for dining in between—two of the town’s top restaurants are on the same Main Street block. Make reservations at the chic Oakhart Social and indulge in creative veggie dishes like brussels sprouts coated in a Korean chili aioli. The nextdoor Public Fish & Oyster defies its inland status and serves up incredible seafood, including a raw bar brimming with plump and briny Virginia oysters.

While these spots are only steps away from the hotel, it’s an easy town for walking off any decadent dining. An afternoon stroll around the campus grounds or a post-dinner walk through the brick-paved historic Downtown Mall is a perfect way to round out a relaxing day in Charlottesville.


The Monticello Wine Trail includes more than thirty wineries, all within an easy—and scenic—drive from downtown Charlottesville. Stop for lunch at Pippin Hill Farm & Vineyards, where the patio offers panoramic mountain views paired with seasonally inspired food from the onsite farm. And spend a sunny afternoon on the hillside at Veritas Vineyards and Winery, which features a similar elegant mountain-farm appeal alongside some of the region’s best Old World wines.

Perhaps one of the most fun vineyard experiences, though, can be found at King Family Vineyards, where crowds gather every summer Sunday afternoon to enjoy both the vineyard’s wine and its famed polo matches, all with the picturesque backdrop of the Blue Ridge Mountains.