City Cheat Sheet: A Travel Guide for Charlottesville, Virginia

Photography by Jen Fariello Photography.

WHY VISIT THE DYNAMIC UNIVERSITY TOWN of Charlottesville, Virginia? Christy Ford and Susie Matheson, The Scout Guide co-founders and co-editors of The Scout Guide Charlottesville, can name a few reasons. This bustling and bucolic city offers mountain views, top-notch food, unique boutiques, and a bevy wineries. Here, Christy and Susie share their favorite local finds and activities for taking in their city.

*Please note that due to COVID-19 some of these businesses might be closed or have specific guidelines in place. We recommend calling ahead and/or visiting their websites for the latest information on their status, offerings, etc. 

WHEN TO GO // Because of its Mid-Atlantic location and relatively temperate climate, Charlottesville is an excellent place to visit year-round. In the spring, the city bursts into bloom, with a stunning show of cherry blossoms and azaleas. Summer, when the University of Virginia is not in session, offers a slower pace, while early fall brings spectacular foliage (which makes for a stunning drive out to surrounding wineries).

WHERE TO STAY // Quirk Hotel (499 West Main Street). A highly “Instagrammable” hotel that has won multiple awards for their design. With amenities like an upscale restaurant, rooftop bar, coffee shop, and art gallery, you may never want to venture out—but please do!

Stay Charlottesville. A locally owned and online-operated business that allows travelers to rent a vacation home in Charlottesville for as little as two days or as long as you need. The housing options range from a large abode in wine country to a downtown apartment.

Oakhurst Inn (122 Oakhurst Circle). A small, well-appointed inn nestled in a residential neighborhood close to the university.

Keswick Hall (701 Club Drive, Keswick). A luxury resort just outside of town. We suggest making time to lounge by their gorgeous pool. Note: Currently undergoing renovations, slated to open in Spring 2021.

Waterperry Farm (4284 Ballards Mill Road, Free Union). Located just 20 minutes from downtown Charlottesville, it’s the perfect escape with pristine gardens and Blue Ridge Mountain views.

WHAT TO DO //  Monticello (931 Thomas Jefferson Parkway). You can’t come to Charlottesville without taking in a little bit of the history surrounding Thomas Jefferson. Whether you choose to simply stroll the grounds or take a guided tour, a visit to Monticello shouldn’t be missed.

Well Room (134 Tenth Street Northwest). If you are looking for some self-care, replenish with one of their IV infusions, relax in the infrared sauna, get a healthy glow with a natural spray tan, or stock up on their apothecary goods. 

IX Art Park (522 Second Street Southeast). An outdoor art park featuring murals, sculptures, and installations that is perfect for the whole family.

Birdwood Golf Course (410 Golf Course Drive). Located at the stunning Boars Head Resort, the newly redesigned Davis Love III Course is a golfer’s delight.

University of Virginia. A UNESCO World Heritage Site, enjoy a walk on Grounds at UVA. Be sure to check out the private gardens just off the Lawn, hidden behind serpentine walls.

pūrvelo (1000 West Main Street). For a fabulous workout while visiting, check out this studio for inspiring cycling classes.

WHERE TO SHOP // Scarpa (2114 Barracks Road). This stylish shop offers a wonderful collection of high-end women’s fashion, accessories, and beauty products.

eloise (505 West Main Street). Browse the highly curated selection of breezy tops and stylish frocks perfect for visiting a vineyard or enjoying a night out on the town at this women’s boutique.

Quattro Tizi (109 First Street South). An upscale urban, contemporary men’s and women’s clothing and lifestyle store on the downtown walking mall.

And George and Hasan’s Rugs (3465 Ivy Road). Just a short drive down scenic Ivy Road, this two-for-one shop features home furnishings, gifts and antiquities curated by designer Jan Roden as well as the recent addition of Hasan’s Rugs, purveyors of handmade Turkish rugs.

Be Just (407 Monticello Road). A beautifully curated homewares store with a backroom filled with a variety of lovely plants to purchase.

Darling Boutique (115 First Street South). A consignment boutique with a focus on jewelry and accessories from local artisans. 

Natalie Dressed (1051 Millmont Street). A women’s consignment store featuring high-end pieces and wardrobe staples.

New Dominion Bookshop (404 East Main Street). Located on the downtown mall, the oldest independent bookseller in Virginia.

Circa (1700 Allied Street). A vintage home goods and furniture store you could get lost in for an afternoon. You’ll be hard pressed not to discover some gems. 

Alton Lane (112 Fourth Street Northeast). A menswear shop founded by two UVA grads that offers a vast array of custom shirt and suit options.

WHERE TO EAT & DRINK // Red Pump Kitchen (401 East Main Street). Italian and Mediterranean cuisine served in a warm and cozy setting on the downtown mall. Coveted patio seating offers some of the best people-watching in town. Currently serving as an outpost for their sister winery, Pippin Hill Farm & Vineyards. 

MarieBette (700 Rose Hill Drive) and Petite MarieBette (105 East Water Street). This cafe and bakery makes for a delicious brunch spot thanks to delicious pancakes, pastries, sandwiches, and more. While there, don’t hesitate to grab a latte and a treat for the road or a stroll down the mall. 

Pippin Hill Farm and Vineyards (5022 Plank Road, North Garden). A picture-perfect winery with cheese boards to match. This is the type of place to inspire spur-of-the-moment photoshoots.

Bowerbird Bakeshop (120 Tenth Street Northwest). Everything is delicious here, but be sure to grab one (or a few) of their macarons. We especially love their vegan offerings. 

Peloton Station (114 Tenth Street Northwest). Upscale bar food with fresh, local ingredients.

Dairy Market (946 Grady Avenue). A recently opened, multi-vendor food hall that gives you a taste of some of the best Charlottesville has to offer.

Brazos Tacos (925 Second Street Southeast). Their Austin, Texas-style breakfast tacos are a local favorite, but don’t stop there. This IX location hotspot also has some of the best margaritas in town. 

Lampo (205 Monticello Road). A Neapolitan pizza place with phenomenal pies, meatballs, and cocktails. 

Tavola (826 Hinton Avenue). A popular Italian dinner spot with outstanding pasta and a wine and cocktail menu to match. Their bar in the back has fabulous NYC vibes. 

The Alley Light (108 Second Street Southwest). One of the hardest places to get a reservation, and for good reason—a meal at this upscale restaurant makes for a perfect night out. Pro tip: you can usually snag a spot at the bar.

The Pie Chest (119 Fourth Street Northeast). Selling both sweet and savory pies, including breakfast hand pies. This spot closes at 4:00 p.m., so enjoy a slice in house and be sure to bring one home for a post-dinner treat. 

LOCAL PRO-TIP // As mentioned above, Charlottesville is a university town. Make sure to check the university schedule for events at UVA before you visit, as they can really change your wait times at local hotspots—especially during graduation.

You can download this Charlottesville cheat sheet by clicking here. For additional recommendations for what to do, see, and experience in Charlottesville, Virginia, follow The Scout Guide Charlottesville on Instagram.