Charlottesville, VA: The Lady’s Pocket Guide


Charlottesville, Virginia. Not a place you would normally stop in North America, it’s home to an endless amount of college kids jogging the cobblestone streets, Thomas Jefferson’s Monticello, and the rolling hills of wine country, here is a pocket guide of what awaits you in quasi-undiscovered Charlottesville.

FREE Happy Hour

  • Market Street Winery: Every Wednesday night there is a free beer tasting flight which is so underground it is underground!  The beers are accompanied by complimentary cheese and breads.  The beers change each week and the owner is super educated about his IPAs and lagers.  For the wine lovers rest assured- there is a huge selection of bottles all categorized by country and they make for an affordable girls night in at your bnb of choice.

Adorable Bed and Breakfast Stays

  • The Inn At Court Square: Pricey but so worth it. It overlooks the court square and the bedrooms are furnished in an adorably Victorian/feminine way. Treat yourself to bubble baths in your whirlpool tub, bath caviar, and a selection of quiches for your breakfast. I stayed here for 3 days and upon arrival was greeted with a glass of white wine and news that I was upgraded to a mind boggling suite! Fluffy pillows, delicious personal Jacuzzi, room service…just what a girl deserves after a long time on the road.

Kitschy hang outs

  • Stroll the Downtown Mall: Wear or buy something nice at one of the many boutique shops, or opt for more affordable swag at the outdoor vendors. The downtown mall is a people watching haven and has unique concept restaurant, such as the Whiskey Jar and Mud Cup café.

  • Tour the University of Virginia: Pick a nice day and prepare to get your undergrad nostalgia on! UVA hosts hourly historic tours of their rotunda daily and the guides are adorable young undergraduates who are knowledgeable and filled with pride for their school. UVA is a beautiful campus and steeped in tradition that many colleges today lack.  If you are lucky your tour guide might just talk a little bit about the secret societies on campus. For added relaxation pull up some green on the main lawn and watch the seniors take in their waning year of freedom.

Local Spot of Choice

  • Beer Run: Near the Belmont area of town, opposite the direction of UVA, Beer Run is a local joint which I would have only found by way of a fun loving local guy. Here we delighted in mile high nachos, craft beers galore, and super friendly wait staff. If you like your beer feel free to purchase a six pack; the whole place doubles as a beverage center reminiscent of 7-11.

Nightlife & Drinks

  • C & O:  Catch some “Gypsy Jazz” at night featuring Rick Olivarez’s Trio. Make sure to get a seat so you can observe the band as well as take in the rustic backdrop of the industrial trains whizzing by into the night.
  • Sky Bar at the Common Wealth Restaurant: Feeling swanky and just wanna dance?  This hip rooftop bar is very lounge-esk and hosts DJs on the weekends for getting your groove on.
  • South-Street Brewery:  This large bar/brewery has a ski lodge feel to it with a real fireplace for cold nights and live music often.  Unpretentious and unassuming—cozy up here with that new guy of yours and sample his cold flight of beers 😉

Get outdoors!

  • Skyline Drive: If you are entering C-Ville from the north or heading directionally north—go by way of the “Skyline”.  This is a GORGEOUS ride located inside the Shenandoah National Park.  It is particularly stunning in the fall; I drove it in late October after leaving DC and it was a wonderful way to shake off the big city feeling.  The road is a 35mph series of curves and switchbacks and over 65 lookout points.  You can stay as long as you want at each one.  There are approximately  3-4 entrance/exits to the skyline drive so if you want to head off before it terminates on I-64 (this taken east brings you right into C-Ville) no worries, just “take ramp right”.
  • Roadside stops: Stop at the shops just outside of Monticello on the roadside!  They have apple butter, ciders, and apples as well as homemade crafts.  Carter Mountain Orchard is a great one to start at!

Cool Find just a bit away from Charlottesville

  • Crozet Pizza: Located on the back porch of Charlottesville, head west to the town of Crozet to eat at Crozet pizza. This little guy was cited in USA today’s “51 great pizza parlors” and sure lives up to this esteemed notation.



About Author

Traci is a bold New Yorker who loves taking her empire state of mind global. She holds a degree in International Business, and bleeds humanitarianism. Traci spent a semester in 2007 living in Italy and bouncing around Western Europe. In the past 3 years she volunteered at a homeless shelter in California, worked construction in New Orleans, and moonlights as a bartender everywhere she goes. She recently completed an epic 7 month backpacking trip through Central and South America and spent a month road-tripping the East Coast. Check out her personal blog at Based out of: New Orleans, LA


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