City Cheat Sheet: A Travel Guide for Charlottesville, Virginia

Thanks to vineyards offering mountain views, numerous noteworthy restaurants, and an historic college town backdrop that exudes charm, Charlottesville, Virginia, is a popular destination for weddings, wine-tasters, and, of course, anyone visiting University of Virginia for a weekend. Whether you’re coming into town to celebrate graduation or planning a getaway with your four-legged friend in tow, this is a city best enjoyed like a local. Here, The Scout Guide Charlottesville Editor Ian Dillard, a native Virginian and UVA grad, shares recommendations for a weekend in his city, including getting some mountain exercise, sampling the regional rosés, and sharing tapas with friends.

Where to Stay

Stay Charlottesville is a locally owned and operated online business that allows visitors to rent a vacation home in Charlottesville for as little as two days, or as long as you need, and the housing options range from a large abode out in wine country to an apartment right downtown. If you’d rather stay at a hotel, Ian recommends the upscale, pet-friendly boutique option The Draftsman (1106 West Main Street), a Marriott property with a local bent. Everything you’ll find at this hotel is local—from the booze at the bar to the reading material in your room (hint: Ian edited it).

What to Do

Charlottesville is an active, outdoorsy place, so if you like to start your day out with some exercise—inside, outside, or both—you’re in luck. “Whenever I have out-of-town guests, I make them take my cycle class,” says Ian, who teaches at purvelo (1000 West Main Street) at 9 or 10 a.m. on Saturdays, and at 3 p.m. on Sundays. After class, he always strolls through the Farmers Market (100 Water Street, from 7 a.m. until 12 p.m.), stopping to visit with the city’s makers and entrepreneurs and pick up a post-workout snack or supplies for lunch (Ian’s favorite treat is the Brown Sugar Pie from the Family Ties and Pies stand). Charlottesville is also known for hiking, and Ian’s favorite path is the one out to Humpback Rocks. “It can be a little challenging, and your ears will definitely pop,” he warns. “But it’s totally worth it for the endless views.”

If you want a view you don’t have to work for, preferably with a side of wine, then head out to the vineyards. Ian recommends Pippin Hill Farm & Vineyard (5022 Plank Road in North Garden) for its breathtaking, Instagrammable vistas and refreshing rosé. Early Mountain Vineyard (6109 Wolftown-Hood Road), located north of town, has more gorgeous views and a cozy, fireside feel. King Family Vineyards (6550 Roseland Farm in Crozet), situated in the foothills of the Blue Ridge Mountains, is another gorgeous place to sip and take in the scenery. On summer weekends you can catch polo matches there while enjoying their “Crosé” (rosé produced in Crozet). And if you’re more into spirits, head to Ragged Branch distillery (1015 Taylor’s Gap Road) to sample Virginia Straight Bourbon Whiskeys or a signature cocktail while taking in panoramic views of the Ragged Mountains.

Where to Shop

For a taste of the local shopping scene, Ian recommends strolling around the downtown mall and popping into some of his favorite shops. Roxie Daisy (101 East Water Street) is a gorgeously curated store with clothing, home goods, one-of-a-kind gifts, and the latest issues of Kinfolk— Ian’s favorite reason to pop in. Dapper gentlemen will want to wander into Alton Lane (112 Fourth Street Northwest), a bespoke menswear shop founded by two UVA grads that offers a vast array of shirt and suiting options. Meanwhile, women in search of chic yet wearable pieces should pay a visit to Honey Ryder Boutique (407 East Main Street) and e.g. (115 1st St S.) . In need of a vacation read? New Dominion Bookshop (404 East Main Street) is a spacious, independent bookstore, and Rock Paper Scissors (321 East Main Street) is a stationery store full of unique paper goods, including cards to send home.

On Fourth Street you’ll see signs for “Pies,” “Flowers,” and “Candy,” as if you have entered a quaint lane from a fairy tale. Don’t miss any of these shops. “Pie” is The Pie Chest (119 4th Street Northeast), where you can enjoy slices of sweet and savory pie and delicious coffee. “Flowers” is Hedge Fine Blooms (115 4th Street Northeast), a lovely shop where you can pick up a bouquet to gift to your host or decorate your room for the weekend. “Candy” is The Candy Store (114 4th Street Northeast), which is stocked with more than 3,000 different types of candy. (Pick a few to carry in your purse while you shop.)

For a beautiful collection of women’s fashion, accessories, and beauty products, pay a visit to Scarpa (2114 Barracks Road), where the friendly and knowledgeable staff will help you navigate the stunning showroom. You’ll also want to head over to West Main Street, where women’s boutique eloise (505 West Main Street) offers a highly curated selection of breezy tops and stylish frocks perfect for visiting the vineyard or enjoying a night out on the town.

Where to Eat

A weekend staple for Ian and his friends, MarieBette (700 Rose Hill Drive) is a must for brunch. “I literally love everything there, from the pancakes to the sticky buns to the croissants,” he says. For something on the healthy side, he recommends a Superman Bowl from The Juice Laundry (722 Preston Avenue, #105). Another delicious breakfast option is Brazos Tacos (925 Second Street Southeast), which is part of IX Art Park. “Their breakfast tacos are famous,” Ian says of the local favorite.

For dinner, you can’t go wrong with Lampo (205 Monticello Road), a Neopolitan pizza place with phenomenal pizza, meatballs, and cocktails (just be prepared to wait—seating at this shoebox-size restaurant is limited). Mas Tapas (904 Monticello Road) is another popular spot where it’s worth waiting for a highly coveted table to sample the tasty options off the eclectic menu (Ian’s picks always include the smoked roasted tomatoes and a pitcher of sangria). The Alley Light (108 2nd Street) is a hidden restaurant and one of the hardest places to get a reservation in Charlottesville, but you can always find a spot at the bar and enjoy a cocktail crafted by bartender Micah LeMon, who just published a book on the art of the cocktail. Finally, Smoked Kitchen and Tap (2025 Library Avenue in Crozet), located just out of town, has the best barbecue in the area plus a huge rooftop bar with lovely views.

For more insider’s tips on what to do and see in Charlottesville, follow Ian on Instagram. Discover excellent independently owned businesses in Charlottesville in the TSG Charlottesville Directory, or order a copy of The Scout Guide Charlottesville. Photography by Ashely Cox Photography.