Travel Guide: Charlottesville, Virginia

Mild temperatures. Small town charm. History. Hiking. Wineries. Local antiques and boutiques. As we looked for our next destination for our annual fall girls vacay, Charlottesville, Virginia seemed to check off most of the boxes.

Home to the University of Virginia, Charlottesville is certainly a college town, but it’s also a perfect spot for a weekend getaway. On the outskirts, lies Thomas Jefferson’s mansion, Monticello, as well as Shenandoah National Park (one of my personal favorites). We usually stay in Airbnbs, but for this trip, a hotel in the main part of town seemed like the best option. Our hotel was a short walk to restaurants, shops, and coffee shops. I appreciated the walkability of the downtown Charlottesville area that is filled with thrift shops and antiques, boutiques, and restaurants with areas to eat outside.

If you’re a Mellow Mushroom pizza fan, they have one in Charlottesville. This a spot we used to frequent when we lived in Florida. Charlottesville has a number of smaller breweries. We visited Dairy Market, which is a food court style eatery with different options like Thai, burgers, sandwiches, salads, pizza, and ice cream.

I’m going to highlight three places that I really enjoyed visiting on this trip: Monticello, Shenandoah National Park and Pippin Hill Farm & Winery.


One of the most iconic places to visit in Charlottesville is Monticello, Thomas Jefferson’s estate, slave quarters and gardens all atop a mountain. It has been opened to the public and maintained for almost 100 years. I’ve toured a good amount of historical homes and landmarks, and I would say Monticello is one of the most interesting places I have toured. The property and gardens were stunning and impeccably maintained. I bought a number of their harvested seeds in the gift shop so I can try to grow my own flowers and veggies at home. Their velvet-like cockscomb flowers are showstoppers! So gorgeous.

Let me say that while initially stunned with the beauty of the property, I realized that the history textbooks we read back in elementary school left out quite a bit about Thomas Jefferson and his life. While his political accomplishments such as the Declaration of Independence and the Virginia Statute for Religious Freedom are certainly important, there’s the truth about his day to day life. It’s estimated that during his lifetime, he owned more than 600 slaves. So while I admired the beauty of the gardens and dreamed about the variety of crops you could grow, I was quickly reminded of the men, women, and children who sweat and labored there, serving their master. Straight from Monticello’s website, Thomas Jefferson said “all men are created equal” yet he enslaved them. Seems he lived a double life.

I appreciated that Monticello told the whole story to the best of their ability, including the story of Sally Hemming and her six children fathered by Thomas Jefferson as well as the stories of hundreds of Jefferson’s slaves. Visiting the box-like slave quarters puts everything into perspective: the harsh reality that was many of their lives. Monticello has a designated slavery tour to learn more about the stories and experiences of the people who labored on the plantation.

Shenandoah National Park

If you want to see pretty fall foliage and mountain views, head to Shenandoah National Park, which is only a 30 minute drive from Charlottesville, VA. The drive to the entrance station was very foggy, but still, we had to stop along the side and take pictures of the mountain views from each angle. We weren’t spending much time there, so we decided to go for a shorter hike with a great view; we hiked the Blackrock Summit Trailhead. This short hike took us to a rocky slope of blackrock with a mountain view. Stunning! (see pictures) Skyline Drive is 105 miles of pretty scenery as you drive through the park. If I revisit, I would love to explore the waterfalls and some more Mountain View trails. I highly recommend visiting if you are staying nearby in Charlottesville or another city.

Pippin Hill Farm & Winery

This picturesque winery is straight out of a magazine. From the moment you pull into the parking lot and catch a glimpse of the grounds, you know this place is special. We grabbed a wine flight and found a cozy spot on their outdoor terrace. The wine was delicious and the atmosphere so cozy and comfortable. Their kitchen and menu is a farm-to-table, fresh type of cuisine with small bites to accompany the wine. This is the most beautiful winery I’ve ever been to! We wandered around the grounds, looking at the farm animals and their amazing field of cosmos in full bloom. This would make the most beautiful venue for a wedding or event. If I was local, I would go here again in a heartbeat.

Author: Kelley Spencer

Kelley is a Christian author, gardener, recovering perfectionist, overthinker, mental health advocate and mother of two boys (and one angel) living in the Midwest. She loves tacos, being active outside and planning weekend getaways. Her story, Radical Obedience, was published by Dayspring in Sweet Tea for the Soul. Kelley has God-sized dreams of publishing several books and Bible Studies designed to reach others for Christ in their most vulnerable, painful circumstances.

Leave a Reply