Nestled among the Blue Ridge Mountains likes the town of Charlottesville and its surrounding wine country, perfect for a picturesque weekend getaway in Virginia. Whether you’re looking to wine and dine or spend the day mountaineering among Virginia’s very own national park, Virginia has something to offer for every type of traveler. This blog post will guide you through a memorable weekend, with the best things to do in Charlottesville and the Shenandoah Valley!

Disclosure: Some of the links included are affiliate links, meaning that at no additional cost to you, I will receive a commission if you click to make a purchase. I don’t recommend anything I wouldn’t personally use, and the income goes towards keeping my blog updated!

Where to Stay

When staying in or around Charlottesville, Virginia, add Crozet Carriage House Airbnb to the top of your list! This spacious private suite is the perfect weekend retreat located in Crozet, Virginia. Its modern farm house charm and mountain views along the rolling hills of the property provide a scenic escape, while still being close to all the region has to offer! It is located just 20 minutes outside of Charlottesville, about 1 hour from popular trailheads at Shenandoah National park, and within minutes from fantastic local wineries!

If you’re looking to closer to the city, Boar’s Head Resort is another great option located in Charlottesville, equipped with several swimming pools, a golf course, a sports club, and multiple dining options for the ultimate summer retreat!

Day 1: Discover the Charm of Charlottesville 

Start your day with breakfast at MarieBette Cafe and Bakery, where you will find an array of freshly baked pastries, breads, and quiches. MarieBette has delicious food and it is a hot spot for breakfast, especially on the weekends, so be sure to go early to catch a table! 

After filling up on some sweets, make your way over to Monticello, Charlottesville’s historical landmark, and the former home of Thomas Jefferson. Here you will tour around the beautiful property and gardens, and learn about Thomas Jefferson’s life with emphasis on his involvement with slavery. A self-guided tour ticket can be purchased for $32, or if you’re just looking to enjoy walking around the grounds, you can purchase tickets for $22. There are many different types of tours available depending on what your interest is or if you’re visiting with kids.

For lunch, head over to the charming Downtown Mall, one of the largest outdoor walking malls in the country. Here, you will find cute boutique shops as well as dozens of fantastic restaurants for lunch. Afterwards, spend some time strolling around the beautiful UVA campus, designed by Thomas Jefferson. Admire the classical architecture, including the iconic Rotunda and the serene Academical Village, which is a designated UNESCO world heritage site. 

Day 2: Explore Shenandoah National Park

One of the best parts of Virginia is Shenandoah National Park! There are so many hikes for both beginner and experienced hikers to enjoy with amazing views of the Shenandoah Valley and Blue Ridge Mountains. Some things to note include the park pass, which costs $30 per car and is valid for 1 week. Before entering the park along Skyline Drive, you will find a toll booth where you show your pass or can purchase one. It’s a good idea to purchase your park pass online in advance to avoid waiting in line. If you’re not a hiker, there are still dozens of scenic spots to park the car along Skyline Drive to take in the beautiful mountain views!

The most popular hike is Old Rag, which is roughly a 9 mile loop with summit views and a rock scramble. This is the most popular hike in Shenandoah National Park, and also the most challenging! That being said, it can get busy especially during the weekends. The hike requires a $1 reservation to ensure it doesn’t get too packed. I recommend reserving your spot several days in advance if you plan to do the hike during the weekend or on a holiday! 

Mary’s Rock is another popular hike on the West side of Shenandoah National Park, and is a great sunset hike for unobstructed scenic views! Mary’s Rock Summit can be reached from the Panorama Parking area for a 3.7 mile round trip hike, or via the Pinnacle Picnic Area for a 7.2 mile round trip hike. I went during a holiday weekend and didn’t encounter too many people on the hike until I reached the summit. That being said there was still plenty of place to sit on the rocks with a snack, take pictures, and enjoy the views! This is a moderate hike that is not technically challenging, however, involves primarily trekking uphill, but the view at the summit is certainly worth it! 

Finish your day off with dinner back in Charlottesville at Zocalo, a Latin American restaurant right in town. This restaurant exceeded my expectations, with really flavorful meals and lovely outdoor seating! I highly recommend the salmon!

Day 3: Wine Down at Local Award Winning Wineries

Charlottesville, Virginia is the closest thing to Napa Valley on the East Coast. There are hundreds of beautiful wineries along the Monticello Wine Trail to try. My favorites are Pippin Hill Farm and King Family Vineyards, however, other renowned vineyards include Jefferson Vineyards, Barboursville Vineyards, and Merrie Mill Farm and Vineyard.

Pippin Hill Farm is located in North Garden, about 20 minutes outside of Charlottesville. This stunning winery has made it on the cover of many magazines, is the hot spot for weddings, and is a perfect place to spend your afternoon indulging in wine or their fresh appetizers. Pippin Hill Farm is most famous for its driveway lined in hydrangeas, the perfect backdrop for any photoshoot! The winery itself is in a modern barn with picture perfect mountain and vineyard views. This scenic vineyard is a must on your wine trail list! 

Another must on your Virginia wine trail list is King Family Vineyards. Not only is this a winery, but they also hold polo matches every weekend free of charge! Guests are able to purchase a flight or glass and view the match from the tasting areas, or you can purchase a bottle and pack some snacks to view from the sidelines. If you’re feeling extra adventurous, King Family Vineyards offers polo lessons! Whether you choose to be on horseback or viewing from the sidelines with a glass of wine, is such a fun and unique experience, and certainly a must when visiting the Charlottesville area!  

If you have enough energy to spare, end your day by hiking to the summit of Humpback Rock for sunset. This scenic hike on the Blue Ridge Parkway can be reached through various access points, but the most popular one point of access is via the Humpback Gap parking area, which gives access to the summit via a 2 mile hike. This hike is quite strenuous and the summit is reached in an average of 40 minutes. It is completely uphill with several benches along the way to stop if needed. Once you reach the top, you will see the massive Humpback Rocks, which many hikers climb for sunset. The view is absolutely stunning and one of my favorite all time hikes!