1. Chester Gap Cellars 2009 Petit Verdot at The Inn at Court Square:
Relax by the fire with a robust glass of my favorite local Petit Verdot. Enjoy talking with friends and other travelers in the beautiful living room, decorated with vintage antiques mixed with mid-century art.

2. Mary Lou Mule at Alley Light:
Enjoy the best Mule in town at the Alley Light, known for signature cocktails that use homemade ingredients. A delicious combination of Reyka vodka, house ginger beer, and house bitters, this amazing cocktail is served in a chilled copper mug, making it seem like the perfect drink for an adult Harry Potter. Drinking the Mary Lou Mule is easy, but finding the restaurant can be a bit of a challenge, since there is no sign. Locals in the know, turn down 2nd street’s small alley and look for the light above the door…

3. Big Easy at Commonwealth Sky Bar:
It’s hard to choose just one drink from the long list of signature cocktails offered on the roof of this fun and trendy restaurant, but the Big Easy combines the flavors of the South in a tasty treat: Southern Comfort, apple cider, and Ango Bitters. Enjoy this tasty drink hot or cold from the rooftop bar overlooking the Downtown Mall. This venue also gets my vote for best people-watching spot!

4. White Russian at C&O Restaurant:
Indulge in the classic, creamy cocktail while treating yourself to the quintessential Charlottesville dining experience in this upscale, country French restaurant famous for its exquisite cuisine and elegant atmosphere. With six different dining areas, guests enjoy an intimate dining experience amidst exposed brick walls and salvaged barn wood. I love the small intimate downstairs space.

5. Twinkle Berry Vodka Tonic at Court Square Tavern:
Enjoy this timeless staple with pomegranate berries at an authentic tavern, where locals gather for the rustic, warm feel of a neighborhood meeting place. Located on the corner of Fifth and Jefferson Street, Court Square Tavern is tucked away in the historical heart of downtown Charlottesville and a half block from The Inn at Court Square. Step down into the ground floor tavern of The Old Monticello Hotel and meet Jeff who has been bartending here for over 24 years.