A Guide to Weekend in Charlottesville

By Over The Moon

First time going to Charlottesville or just need to brush up on where to go and what to do? C-ville-based artist Stephanie Fishwick (yes, the woman behind Gwyneth Paltrow’s wedding invitations and all of those hauntingly beautiful collages you’ve likely seen and loved on Instagram) is sharing her guide to this historical city.

“My husband and I both lived in big cities before we met and then settled here: Boston and Washington, D.C. respectively. And for me, it’s important to be surrounded by nature and quiet in order to be creative,” says Stephanie of why she decided to relocated to this quaint southern city.

“Charlottesville features a pretty downtown with small boutiques and restaurants. When James and I were dating we’d frequent an old dive bar on the downtown mall to hear live rockabilly and smoke cigarettes (inside),” Stephanie laughs. “There are still a couple little crumbly bars and bistros to hear music and drink a perfect cocktail. There are also excellent antique shops and country markets tucked throughout the surrounding countryside.”

We would be remiss if we failed to mention the fact that amidst all of the beautiful scenery and authentic nightlife, Charlottesville has seen a lot of political turbulence recently. “For a long time, living here, it was easy to ignore the larger discord in this country,” Stephanie says. “They aren’t new problems, I know. Yet what happened a couple of years ago was a true awakening, like something out of a nightmare. The majority of the people who live here, it seems to me, felt the same way—really shocked and awakened. The memorial for those killed and hurt by the terrorism is still very active in the alleyway off Water Street. We’re all still reeling. It was so awful . . . but the perpetrators were not from our town, which is a very important distinction. It’s sad they chose our town to descend upon.”

And, in the spirit of taking a broken heart and turning it into art, Charlottesville has a rich history of underground artists and musicians who helped revive the downtown into what it is today. “I marvel at the creative careers my friends have carved out for themselves here as professional artists, chefs, musicians (from goth to folk and everything in between), filmmakers, textile artists, entrepreneurs, record store owners, blacksmiths, knife makers, and more. There continues to be a steady stream of ex-city dwellers who move here for a slower pace of life.”

A Little About the History

Founded in 1762, Charlottesville, Virginia was named after King George III’s wife, Charlotte of Mecklenburg-Strelitz, and is now home to around 50,000 people. Two Presidents called Charlottesville home: James Monroe and Thomas Jefferson, and they were both governors of Virginia. (Jefferson famously founded the University of Virginia on the southwest border.) “We benefit from having such a noteworthy university here,” Stephanie says. “And for me that means an endless supply of used books for my collage work!”

Where to Stay

The Clifton

The Clifton

Once you fly into Charlottesville Albemarle Airport (a one hour plane trip from LGA), you’ll want to set your bags down somewhere asap so you can start sightseeing. Fishwick recommends checking into this boutique hotel with 20 newly refurbished guest rooms and taking a quick dip in the pool “to clear your head and relax a bit.” The property also has a restaurant and is available to book as a wedding venue!

Stay Charlottesville

Also recommended by the artist is this vacation rental service. With Stay Charlottesville, you can call the area’s finest carriage houses, apartments, historic homes, and estates, home for a weekend or months at a time. It offers the amenities of a hotel with the privacy and convenience only locals get to typically experience.

Where to Shop

If you’re heading to the Downtown Mall, “stop into Roxie Daisy for French country [home] essentials.” Around the corner from the mall, it is worth checking out “Caspari, Treasures Through Time, The Second Yard, Yves Delorme Outlet, Low Vintage, Daedalus Books, Heartwood Books, and more,” Fishwick says.

Heartwood Bookshop.
Low Vintage.

For amazing antique furniture and housewares, go to Circa. Still on the hunt for vintage pieces? Try “the Ivy Square Shops for (yet) more antiques: The Eternal AtticThe Shade Shop, and Kenny Ball Antiques.”

The Shade Shop

Where to Eat

“No-res required for casual drinks and dinner at Tavola, where you can have a craft cocktail around back at Chicchetti before they seat you for dinner,” Fishwick explains. If you’re not full after that and still looking for a late night dessert or digestif, she recommends to “head to Mas down the street or The C&O downstairs (my favorite).”

The C&O.

On Saturday morning, “stroll through the City Farmer’s Market for breakfast. I love Maria and Ignacio’s Mexican Tacos (steak with everything, a little spicy & crema), a Carpe Donut, Shenandoah Joe’s iced coffee, and many many more. Pickup some local heirloom tomatoes, basil, fresh cheese and a baguette across the street for later,” says Fishwick.

After shopping and browsing near the Downtown Mall, go for a quick and easy lunch at Feast! on Main Street.

Greenwood Gourmet Grocery, in the nearby town of Crozet, is ideal “for an afternoon coffee where you can also find bottles of local wine and other delicious provisions,” Fishwick says.


What to Do

“Drive out to Swannanoa Palace (also a great wedding venue!), and on the way back, stop into the towns of Greenwood and Crozet for more antiques and strawberry picking,” recommends Fishwick. Once you’re back in Charlottesville, “stop into Ivy Nursery for garden inspiration and more European-inspired country decor, linens, soaps etc.”

For live music and art lovers, Fishwick points to venues like The Garage, The Jefferson Theater, The Paramount Theater, and The Southern Cafe & Music Hall.

Feeling outdoorsy? The Rivanna River Company will outfit you with canoes, kayaks, stand-up paddle boards, and tubes, and they have guided tours and youth programs, too!

The Paramount Theater

Click here to read all of Stephanie Fishwick’s Charlottesville recommendations!