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Charlottesville Travel Guide

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There is hardly a better way to spend a fall weekend on the East Coast than drinking wine, dining well, and spending quality time with your best girlfriends. For such a weekend, there is hardly a better place to do so than Charlottesville. The charming, Southern town is rich with architecture, history, and incredible, unpretentious, and charming restaurants. The Virginia wineries have been stepping up their game as of late—so hop in the car, head down south, and enjoy a long weekend of wine, food, and boutique shopping.


Thomas Jefferson’s Monticello

We’re history geeks—so we love a good day at the museum, and try to squeeze in a tour whenever we travel. Regardless of how you did in AP American History, you know that Thomas Jefferson was a pretty interesting guy—you’ll learn first-hand about his experiences with languages, literature, wine, agronomy, the physical sciences (all the contraptions!), and politics during the tour. Tours every 30 minutes. Tickets, $25. Monticello, 931 Thomas Jefferson Pkwy, Charlottesville, VA.


University of Virginia’s Campus

If visiting Charlottesville, you simply must take a stroll through UVA’s campus, with its classic Greco-Roman architecture and its picturesque lawns.



Pippin Hill

If you can only visit one vineyard, make it Pippin Hill, which offers top-notch food, wine, views, and vibes. The beautiful vineyard, restaurant and event space is a top choice for weddings, often doing four per weekend. Read our in-depth review of the food and wine, here. Tastings, $10. Open Tuesday-Sunday, 11am until 5pm. Closed Mondays. Pippin Hill, 5022 Plank Rd, North Garden, VA 22959. (434) 202-8063.


King Family Vineyard

A laid-back, family-friendly affair, King Family Vineyards is a family-owned winery located in Crozet, just fifteen minutes from Charlottesville at the foothills of the Blue Ridge Mountains. The vineyard has an enormous patio, with plenty of seating under umbrellas, making it perfect for ordering a bottle of wine, packing a picnic (or buying one there!) and staying for awhile. The vineyard and its enormous lawn back up against the polo fields, and we were lucky enough to go on a day when polo took place! The folks in the tasting room are friendly, and the Meritage was our favorite. Tastings are $7 a person. Open daily 10 a.m. to 5:30 p.m. King Family Vineyards, 6550 Roseland Farm, Crozet, Virginia 22932, (434) 823-7800.

Veritas Vineyard & Winery

We loved every minute at the darling Veritas, with its beautiful white porches, vine-laden gazebos, and charming view over its vineyards. We arrived in the late afternoon, and sat in the shade reading and drinking the white wine. Veritas Vineyard & Winery, 151 Veritas Lane, Afton, VA 22920. (540) 456-8000.

Trump Vineyard

Regardless of how you feel about the Presidential candidate, Trump vineyard has two things Bitches love: champagne and a great view. The vineyard overlooks more than 1,300 acres of breathtaking rolling hills—perhaps the best view we’ve seen in Charlottesville. Plus, it’s only a few miles from Thomas Jefferson’s Monticello. Inspired by Jefferson, Trump’s vineyard makes new world wines inspired by the French wine regions of Bordeaux and Champagne from its nearly 200 acres of vines, large lakes, and rolling Blue Ridge views. Open year round 11am-5pm daily. Trump Winery, 100 Grand Cru Drive, Charlottesville, VA 22902. (434) 977-3895.

Dinner & Cocktails

The Alley Light

Like its namesake, this speakeasy-style spot is found by finding a lantern above an unmarked door in an alley. The dimly lit cocktail bar is upscale vintage cool, and filled with the beautiful people of Charlottesville. The cocktail program—complete with vintage glassware and handsome Virginia-bred bartenders—can’t be beat. We’d recommend the Dealer’s Choice—the bartenders won’t steer you wrong. We also had the most amazing vegetables at Alley Light: the cauliflower gratin and the carrots, served with herbs, yogurt, cumin-lemon-orange vinaigrette.  The Alley Light, 108 2nd St. S.W., Charlottesville, VA.

C&O Restaurant

C&O is an absolute must when visiting Charlottesville. Sneak through the narrow row house to the restaurant’s courtyard, which feels like a hidden, romantic secret you’re the first to discover. With its brick lights and string lights, it’s the perfect spot for cocktails, which are top notch. The food is fresh, seasonal, and unique. Don’t miss the whiskey cocktails, the beef tartare and the  Russet potato gnocchi with duck confit. C&O, 515 Water Street, Charlottesville, VA.

Mas Tapas

Located across town from Campus, Mas Tapas is a cool spot in an up-and-coming part of town. The Spanish spot has an expansive, patio-laden patio and multiple levels. It serves a delicious sangria, by the pitcher, and fresh, well-executed Spanish small plates. It’s great place for a group dinner or if you’re tired of American fare. MAS Tapas, 904 Monticello Rd, Charlottesville, VA.


Red Pump Kitchen

Red Pump serves accessible, Italian food that’s fresh, seasonal, and satisfying, with an abridged but effective wine list. The restaurant itself is chic, modern, and spacious, with an open kitchen, sexy bar, and ceiling high windows that open onto Main Street. It’s perfect for girls night, or date night. We loved the salads, soups, and the desserts—oh my god, the desserts. Red Pump Kitchen, 401 E Main St, Charlottesville, VA.





This boutique is filled with casual, college-friendly clothing, accessories and boots. We appreciated the wide selection of Frye boots and affordable, unique jewelry and sunglasses. The store carries brands like Free People, Jack, and plenty of plaid. I left with an adorable dress that only cost $64! Bittersweet, 106 E Main St, Charlottesville, VA.


Low Vintage

Just off the Main Street lies Low Vintage, a veritable treasure trove brimming with cowboy boots, fabulous hats, and designer frocks. We had a heyday trying on 80s Oscar de la Renta gowns, and ‘50s style frocks. I went home with a gorgeous Southwestern skirt for a mere 30 bucks—took it to the tailor and it fits like a dream. It’s a must visit—even if you leave empty handed. But, don’t—buy a great pair of vintage earrings. Low Vintage, 105 5th St SE, Charlottesville, VA.

Spring Street Boutique

This preppy, cute enclave is great for printed cotton frocks, hostess gifts, and travel/resort wear—think cover ups, beach bags, and the like. For those looking for something chic, it may not be the best option, but there are cute pieces worth a perusal. Spring Street Boutique, 107 W. Main St., Charlottesville, Va.



Oakhurst Inn & Café
We loved every second of our stay at the cozy, charming and friendly Oakhurst Inn & Café. Decorated in greens, blues, and whites, the Inn has a traditional, Southern style. We appreciated the small, thoughtful details: the Peter Thomas Roth soaps and lotions, the cozy reading nooks with coffee and Pellegrino, and the warm chocolate chip cookies left with turn down service. Read our brunch review, here.


Bitch Biz: We were hosted by Oakhurst Inn & Café, Red Pump Kitchen and Pippin Hill. This article was written independently by Bitches Who Brunch.

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