An Insider's Guide to Charlottesville, VA

From where to stay to secret gems, The Scout Guide (TSG) Charlottesville editor Heather Sieg plans the perfect trip to her city.

Where to stay for a getaway as a couple: Clifton Inn offers the finest dining and it is quietly romantic. Try to reserve the chef’s table; it’s quite the experience.
 Alternatively, a short drive from Charlottesville, you will find the ultra-romantic Inn at Willow Grove. (I got engaged there, so I’m partial!) Stay in the Butler’s Cottage, and do not miss brunch.

Where to stay when traveling with kids: Keswick Hall, hands down. Just outside of “town” and created originally by Lord Ashley (husband of ladies’ clothing icon Laura), the English countryside meets Virginia Hunt Country at this luxurious yet totally comfortable resort; hotel, spa, 3 pools, fine and informal dining, croquet, tennis, world class golf, equestrian activities, and more. And bring the family pet along too – Keswick Hall is pet friendly! The will set up a bed and leave treats for that “other” member of the family.

Where to go for brunch: Commonwealth Restaurant. The staff is friendly and super energetic, and I have loved everything I have ordered from this Downtown Mall local favorite.
 Want something more simple and down-home? Go to Pigeon Hole just off the UVa Corner. Afterwards, pop across the street to Duo, a Scouted women’s boutique filled with new and consigned treasures.

Where to go for lunch: Bodo’s (3 locations) is a Charlottesville institution and the best darn bagel you will ever eat.
 I also recommend the great salads and roast chicken at Eppie’s on the Downtown Mall, followed by an entire afternoon strolling the Mall…each step finds you another local great.

Where to go for dinner: MAS. The shrimp, aka Gambas al’ Parilla, and Carne Asada cannot be left out of the order.
 At Tempo, Chef Brice Cunningham loves incorporating local ingredients into his modern French cuisine. And TEN serves up the most phenomenal sushi in a super-hip environment. Scouted Rolls: Saki Roll and Kobe Beef Roll.

Where to go for drinks: Sip wine over wood-oven gourmet pizza on the terrace at local gem Pippin Hill. The view is out-of-this-world. For more action, get up on the roof of Skybar (atop Commonwealth Restaurant) for martinis!

Ideal place to celebrate a special occasion: The C&O. Cozy, romantic, ideal. Dine upstairs or go for a celebratory drink in the downstairs tavern. My favorite spot in all of C’ville. Share a dessert over drinks or on the back terrace. For a larger party, rent out their gallery space. (Bonus: they have parking!)

Where to shop: Mid-Town. Market Street – between the UVa Corner & Downtown Mall – is a hub of local pearls.
 Speaking of pearls…Pearl’s Cupcakes is our TSG go-to for a “sweet treat.” They have vegan and gluten-free options. Make sure you pay a visit to Scout’s closet: eloise. They carry AG denim, Dosa tunics, locally made Mi Ossa jewelry, Rebecca Taylor, Alice + Olivia, Roberta Freymann/Roberta Roller Rabbit, and many other designers you usually need to travel to NYC or LA to find. Next door you will find Shenanigans, the most fabulously unique toy and children’s gift store, and Folly, featuring beautiful home accents and accessories. They also carry my favorite wallpaper line, Osbourne & Little. If you’re into interiors but wallpaper is not your thing, just down the block and brand new to Charlottesville is Palette Paint, home to only the best: Farrow & Ball, Fine Paints of Europe, Amy Howard One-Step and others.

Across the street is local food hub, the Main Street Market. Scout stocks up at Feast! (cheese and hors d’oeuvres for every dinner party), the best in meat at The Organic Butcher (grab some of their addictive jerky on the way out), and for a birthday, only a Princess Cake from Albemarle Baking Company will do!

Best fests and other reasons to visit: 
Charlottesville is home to the Virginia Film Festival, which takes place in November, and LOOK3: Festival of the Photograph which takes place in June, during which world-renowned artists congregate in our hometown to celebrate the best in indy film and visionary photography. 
The Montpelier Races, which take place on the first Saturday in November, is a fabulous day of steeplechase, celebrating the equestrian heritage of Virginia at James Madison’s former homestead.

Monticello Heritage Harvest Festival, which takes place in mid-September, brings in guests and presenters from around the world. As they say on their website: “Thomas Jefferson, America’s ‘First foodie,’ championed vegetable cuisine, plant experimentation and sustainable agriculture. Taste a bounty of heirloom fruits and vegetables and learn about organic gardening and seed-saving during this fun, affordable, family- friendly festival — unlike any other — held on the breathtaking West Lawn of Jefferson’s Monticello.”

Where to get pampered: Toby at Moxie does all of our hair here at TSG HQ.
 Serenity Nails for a quick mani/pedi. When it is time to indulge, Neroli Spa for a massage and Signature Medical Spa for the best facial!

Secret Gem: And George. Just west of The Boar’s Head Inn and Farmington Country Club you will find a favorite of world-renowned interior designer Charlotte Moss and locals alike. Owners Christy Ford (Co-Founder of TSG) and celebrated Interior Designer (and Christy’s mother) Jan Roden curate the ultimate in antiques (the Scandinavian pieces are my favorite), home accessories, and gifts. My dream home will one day be outfitted in And George finds. Scarpa is a shoe-lovers dream that keeps us C’villians hip and in the know with current shoe trends. They carry Fiorentini + Baker boots, Pedro Garcia, Vince, and many more.

Ideal Saturday: Charlottesville City Market is a weekly activity for my family. Stock up on the best of local produce, meat (Timbercreek, Double H, Madison Rainbow Trout), jams by Daniel, and Stevie G’s granola. Run across the street to Roxie Daisy for some new Bella Note napkins, Canvas dinnerware, or a hostess gift. They also have the most divine collection of note cards for any occasion. Think of how happy you are when you get a piece of real mail. I love sending it. I have never left Roxie Daisy empty handed.

Drive out to Greenwood for lunch on a picnic table at Greenwood Gourmet (I usually order the Tuscan Chicken Salad) followed by treasure hunting at the Greenwood Country Store. If the season is right, pick our own peaches or apples at Chile’s Orchard. Finish the day with a relaxed dinner by the fire at Keswick Hall with some close friends from the Keswick “neighborhood.”

One piece of insider information: Deemed by Forbes Magazine “the locavore capital of the world,” come to Charlottesville to celebrate all that is beautifully local about this community. Use TSG as your guide; that’s what we’re here for!

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