Charlottesville History
Charlottesville is administratively independent of, but located in, Albemarle County, central Virginia, U.S. It lies on the Rivanna River, in the foothills of the Blue Ridge Mountains, about 70 miles northwest of Richmond, on the main route west from the Tidewater region.
Charlottesville was named for Charlotte Sophia, consort of King George III of England. It grew as a tobacco-trading point and later became famous as the home of presidents Thomas Jefferson and James Monroe as well as explorers Meriwether Lewis and George Rogers Clark.
Jefferson founded the University of Virginia at Charlottesville in 1819 and designed its original buildings (used as hospitals during the American Civil War). The Institute of Textile Technology was founded there in 1944 and Piedmont Virginia Community College in 1969.
(Source: John Werner Kluge. (2020, September 17). Retrieved November 11, 2020, from https://www.britannica.com/biography/John-Werner-Kluge)
Things to Do
Charlottesville is surrounded by historical and natural attractions, and it is a prime area to explore wineries, breweries, and restaurants.
Wineries within 20 minutes of Charlottesville:
1) Jefferson Vineyards (11 minutes)
2) Eastwood Farm Winery (11 minutes)
3) Monticello AVA (14 minutes)
4) Gabriele Rausse Winery (18 minutes)
5) Meriwether Springs Vineyard & Brewery (19 minutes)
Breweries within 15 minutes of Charlottesville:
1) Decipher Brewing (5 minutes)
2) Random Row Brewing (5 minutes)
3) Selvedge Brewing (7 minutes)
4) Reason Beer (12 minutes)
5) Bold Rock Carter Mountain (13 minutes)
Historical Sites within 15 minutes of Charlottesville:
1) CB Holt House (6 minutes)
2) Monticello (9 minutes)
3) Edgar Allen Poe Room (10 minutes)
4) Blue Ridge Sanitarium (10 minutes)
5) James Monroe’s Highland (15 minutes)
Hiking Trails within 20 minutes of Charlottesville:
1) Schenk’s Greenway (4 minutes)
2) The Rivanna Trail – Woolen Mills (8 minutes)
3) Kemper Park (11 minutes)
4) Highland Rustic Trail (15 minutes)
5) Ragged Mountain Nature Area (16 minutes)
Day Trip Overview
On October 6, 2020, I decided to finally take a day to visit Charlottesville, Virginia. Charlottesville is a swift 60-minute drive from Richmond. I filled my gas tank at Arthur Ashe Boulevard and hit the road north to 95 and west on 64. From there, I could cruise. The tall trees lined 64 and gave a beautiful view of Virginia’s fall foliage.
I typed the address for the Market Street parking garage (546 E Market St) into my GPS, and it quickly came up on the left. From there, I walked straight over a few blocks to the Main Street open area mall. I moseyed around until a found a fine place to dine outside. After a lovely lunch on this warm October day, I decided to venture out to the Carter Mountain Orchard, located about 13 minutes from the Main Street area. I was able to view the grandeur of the Charlottesville area, mountains, trees, and vineyards. My final goal was to find a local winery, which was lightly thwarted by the fact that it was a Tuesday, when most wineries were closed. However, there was a little haven just in the city limits where I could get my fix and bring home a special treat for my beau.

Charlottesville Main Street
Charlottesville’s Main Street is a swift walk from the Market Street parking garage. Flourishing with cafes, restaurants, and even a movie theatre, it’s easy to find great entertainment day or night.

Carter Mountain Orchard
Carter Mountain Orchard is the place to go apple picking! If you’re looking to just go outdoors and enjoy a cider-based beverage, this is the place to sit back, relax, and take in the view!

The Whiskey Jar
The Whiskey Jar, hidden at the end of Main Street’s promenade, is worth visiting for their delectable menu and shining examples of mixology!

Wineworks Extended
When all the wineries are closed and you are looking for a flight of fine wine, look no further than Wineworks Extended, the quaint pop-up located in the outskirts of Charlottesville, featuring Michael Shaps’ wine selection.
A Map of My Journey:

Home: Richmond, Virginia
Downtown Parking: 546 E Market St, Charlottesville, VA 22902
Main Street Outdoor Mall: E Main St, Charlottesville, VA 22902
The Whiskey Jar: 227 W Main St, Charlottesville, VA 22902
Carter Mountain Orchard and County Store: 1435 Carters Mountain Trail, Charlottesville, VA 22902
Wineworks Extended: 1585 Avon Street Ext, Charlottesville, VA 22902
How Much Did It Cost?
Money totals: My goal was to keep this under $100. The $35 bottle of wine was by far the most expensive, but I bought it as a gift and thus splurged on it. I’m also not a heavy eater, so I didn’t need much to keep my stomach satisfied. I also waited until home to eat dinner. If the situation was at its most ideal, I would’ve had an aperitif with the wine flight to help combat the alcohol influence and satisfy pre-hunger pangs.
Wawa Fuel: $17.08 (Filling up an empty gas tank)
Lanier Parking: $3.00 (Main Street Parking Garage)
The Whiskey Jar: $23.92 ($18.92 Old Fashioned & Chicken Biscuit Sandwich + $5.00 tip)
SQ *Craft Revolution: $24.30 (12oz Cup of Cider + Cider To-Go!)
Michael Shaps Winery: $58.86 ($10 flight + $35 bottle Petit Verdot + 30% tip)
Total cost of the day: $110.08
Conclusion
I didn’t completely accomplish all I set out to do today. It was very focused on food and beverages over history (not my intention). I feel like my visit is incomplete, and I only have more research to do in order to really experience what Charlottesville has to offer.
Next time, I’d like to explore more of the wineries, which means… traveling on a Thursday, Friday, or Saturday. I’d like to check out more of the historical sites and even go for a walk on one of their many connective hiking paths. I’m not sure how expensive the Monticello experience will be when all is said and done. It felt very touristy, and that’s why I left. I want to find more holes in the wall… local favorites. Maybe I’ll stay the night and do a barhop with locals’ favorite dives. That will likely have to wait until after COVID. I feel so lucky to have been able to explore a new region of Virginia and still stay safe and respectful of others.
I guess I need to come back for another visit!
Great info for a day trip.
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