Charlottesville, Virginia is located in the heart of the Virginia Wine Country, just over 2 hours from Washington, DC. It is home to the University of Virginia, our Founding Fathers Thomas Jefferson, James Madison, and James Monroe, and a plethora of wineries and history. A road trip to Charlottesville, Virginia is perfect, for everyone and all kinds of trips, whether celebratory, family, friends, or solo. I chose the latter and went on a solo road trip to Charlottesville, Virginia last weekend to see family for a work conference. Going to Charlottesville, Virginia on a road trip was nothing short of a blast!

What I Did

To start my road trip to Charlottesville, Virginia, I drove through the beautiful Virginia countryside on Route 29. Living in the Washington, DC suburbs of Northern Virginia, I drove through Virginia’s counties of Prince William County, Fauquier County, Culpeper County, Madison County, and Greene County to get to Charlottesville. Each of these counties are located in the heart of the Virginia countryside and Virginia Wine Country, filled with small businesses lining Route 29 and farms at every corner. True and utter beauty – so much that I wanted to stop at each and every single local business along the way as I jammed out to the 80’s channel on SiriusXM the entire way.

My first stop on my road trip to Charlottesville, Virginia: the University of Virginia. I parked my car right by the bookstore in the parking garage (they’re everywhere along the University of Virginia’s campus and parking lots, too) and set out to explore the campus. The University of Virginia was the first-ever public university in the state of Virginia and potentially the United States (I can’t remember – haha!!). This college was founded by former President Thomas Jefferson after his presidency as he was a resident of Charlottesville and wanted others to have an education like his own. I walked around the breathtaking Rotunda – the main draw to the University of Virginia and asked a student to show me where it was (students are SUPER helpful here!) – which had a statue honoring Thomas Jefferson, himself. After admiring the University of Virginia’s gorgeous and huge campus, I set sail for my conference networking event which was on the campus!

My second stop on my road trip to Charlottesville, Virginia was to see my Aunt Lisa, Uncle John, and cousins Mary, Joey, and Matthew who live in Charlottesville. We enjoyed some much-needed and enjoyable family time that we hadn’t had for years, especially due to the COVID-19 pandemic.

My third stop on my road trip to Charlottesville, Virginia was to check out Grace Estate Winery with my Aunt Lisa and cousin Mary – a vineyard located along the Monticello Wine Trail in Crozet, Virginia which is a nearby-to-Charlottesville town located in the foothills of the Virginia Blue Ridge Mountains. Grace Estate Winery is also a participating Virginia Wine Pass vineyard. The Virginia Wine Pass – which I am a pass holder of – allows for its pass holders to get discounts at its participating vineyards. This excursion to Grace Estate Winery was my first-EVER usage of my Virginia Wine Pass and it was great to treat my Aunt Lisa and cousin Mary to some discounted wine flights, too! Grace Estate Winery was a super duper adorable winery with gorgeous scenic views. It has a precious little selection of merchandise, including wine barrel planters. While I wasn’t the biggest fan of the wine there, the owner was the sweetest and the views were even more beautiful!

My fourth and final stop on my road trip to Charlottesville, Virginia was to nothing short of the Belk – yes, Belk!!! – in Charlottesville on Route 29! They do not have Belk’s in my home base of the Washington, DC area.

What To Do

There is A TON to do on a road trip to Charlottesville, Virginia! This past Fall, I visited Thomas Jefferson’s Monticello – his former homestead for the day and LOVED it. On the same token, there is SO MUCH that I want to do just in and around Charlottesville, Virginia!!

  • Tour James Madison’s Montpelier
  • Walk around the University of Virginia *yet again*
  • Explore downtown Charlottesville
  • Go on a Monticello Wine Trail crawl and visit 3-4 wineries in a day! (some of the wineries/vineyards include: Pippin Hill Farm & Vineyards, King Family Vineyards, Afton Mountain Vineyards, and Veritas Vineyards and Winery)
  • Visit and enjoy local goods at Carter Mountain Orchard
  • Tour James Monroe’s Highland
  • Re-visit and tour Thomas Jefferson’s Monticello

All in all, I had an amazing time on my road trip to Charlottesville, Virginia and cannot wait to go again!

XOXO – Katie <3

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