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Charlottesville, Virginia is one of those towns I just never get tired of! From the charming college campus of the University of Virginia to the endless mountain views, there’s always something new to see and do. We are already naturally drawn to traveling to the mountains, so to get a bit of hiking and a bit of city life makes for the perfect weekend trip. Oh, and I can’t forget to mention the Monticello wine trail that surrounds Charlottesville! No matter what time of year it is, you are sure to have the time of your life visiting this beautiful town. In this article, I’m sharing the best Charlottesville weekend itinerary–from where to stay, what to do, and what to eat.
About Charlottesville, Virginia
Charlottesville is located just about dead center in the state of Virginia. It’s nestled within the beautiful Blue Ridge Mountains and is home to the famous University of Virginia. I guess you could say we have Thomas Jefferson to thank for this cute city, because he designed UVA’s campus and his home of Monticello is just a short car ride away. With a population just under 50,000 this a good sized city that is easy to explore in just one weekend (but you could certainly stay longer!). Charlottesville is in the perfect location for exploring the rest of the state, too. You’re right near the entrance of Shenandoah National Park, James Monroe’s Highland home, and only a few hours away from the nation’s capital.
The university has a strong influence on Charlottesville, so you’re sure to experience a city that is constantly evolving and dare I say ~hip~. The restaurants are excellent, there’s constantly events happening, and the shopping is fantastic for a city of this size! But Charlottesville has still managed to hold onto its historical charm. Beautiful brick buildings spot the campus but have also spilled into its downtown area and influenced the outer edges of campus as well. Everywhere you turn is serious eye candy.
How to get to Charlottesville
Charlottesville is conveniently located in the center of Virginia, making it an easy drive for Virginians and may surrounding states. While Charlottesville does have its own airport, the Charlottesville Ablemarle Airport (CHO), it is quite small and you’ll most likely pay through the nose to fly directly into it. However–if you can swing it, go for it! There are about 50 flights in and out of the airport daily, and it is serviced by Delta, United, and American Airlines. If you’re traveling from New York, DC, or Atlanta you can hop on a short direct flight from your departure airport into Charlottesville.
Coming from a bit farther away and don’t want to pay a premium to fly directly into Charlottesville? I got ya. You can book an inexpensive flight into Washington, DC and drive just 2 short hours to Charlottesville.
For east coasters, Charlottesville is a short drive from many top destinations. Hop in the car and you’ll be here before you know it! Here are some travel times for popular destinations near Charlottesville:
- Washington, DC: 2 hours
- Richmond, Virginia: 1 hour 15 minutes
- Williamsburg Virginia: 1 hour 50 minutes
- Durham, NC: 3 hours 15 minutes
- Raleigh, NC: 3 hours 30 minutes
- Annapolis, Maryland: 3 hours
- Columbia, SC: 5 hours 30 minutes
Charlottesville’s proximity to many other popular cities makes it a great choice for a quick weekend trip.
The Best Time to Visit Charlottesville
Due to its location within the Shenandoah Valley and the moderate climate Virginia experiences, there’s really no bad time to visit Charlottesville. When you take your trip will primarily depend upon what you want to experience!
Something of a wine connoisseur? In the Spring, there are a few different wine festivals like the Taste of Monticello Trail Wine Festival and the Orange Uncorked Wine Festival. And of course, spring is the perfect time to see the beautiful blooming flowers. You can enjoy the Dogwood Festival, Historic Garden Week, or just get lost strolling around to see the beautiful flowers!
Expect the weather to be a bit unpredictable, especially if you go towards the beginning of Spring in late March or early April. You may have cold rain or a slushy snow shower. But you could also luck out and get a warm, sunny day! In late March and April, the average highs are in the 60s (F) but into May you’ll start to get more days in the 70s.
If you can look past the hot temperatures and sticky humidity, Charlottesville is the best time to visit to enjoy the outdoors. With a plethora of mountain trails on Charlottesville’s back porch, you can hike, bike, or just take a leisurely stroll. There’s also a ton of lakes, rivers, and swimming holes to cool off within Albemarle County.
Summer is lively with plenty of events happening outdoors at breweries and parks. Be sure to stop by the seasonal farmers markets, too! Just don’t forget to pack your sunscreen and water!
Is it just me or do you feel like you haven’t truly enjoyed fall until you’ve done it in the mountains? Charlottesville is a fantastic time to enjoy some of the best of Charlottesville. You can expect nearly perfect weather with 60 and 70 degree days (F), perfect for hiking the trails and sipping wine at a nearby brewery.
Because Charlottesville is home to the University of Virginia, you will have thousands of students returning to the area. C’ville is well versed in handling this influx of people but something to keep in mind for hotel and restaurant reservations.
Walkin’ in a winter wonderland! Well… maybe. Winter in Charlottesville tends to be pretty mild. Throughout the winter, the average highs are in the 40s and 50s (F) and snowstorms are infrequent, so you can still enjoy a myriad of outdoor activities. Cozy up by the fire with a glass of wine at a local brewery and spend some more time indoors at some of the historical buildings in the area.
A huge perk of visiting in Winter is enjoying more availability and more affordable prices for some of those aspirational properties in Charlottesville.
Where to stay in Charlottesville
No matter what budget or style you’re looking for, Charlottesville’s got it. Due to the proximity of the University, you can find most of your standard chains if you’re loyal to one brand or looking to burn some points and miles. There’s also a ton of gorgeous, unique and boutique properties in Charlottesvillae, too! I highly recommend staying at one of these B&Bs and quaint inns to add to the magic of your stay!
The Graduate Charlottesville
Graduate Charlottesville is right in the heart of The Corner, which is on Main Street right across from the University of Virginia. The Graduate is actually a unique chain of hotels located in college towns across the country, but each is decorated to honor the university it calls home! I stayed here in the Fall of 2021. The location absolutely can’t be beat and the rooms were comfortable and quirky.
Keswick Hall at Monticello
If you’re traveling to celebrate an anniversary, babymoon, or just a luxurious girl’s weekend, Keswick Hall is the place for you. This resort hotel is located in Keswick, Virginia on 600 acres that encompasses a golf course, a spa, fine dining, and of course, the most beautiful rooms. You technically don’t even need to leave the property to have everything you need! And just look at the pool area….. I die. Keswick Hall is located about 30 minutes outside of Charlottesville, but is right in the heart of wine country if you’re traveling mainly to check out the wineries.
The Inn at Court Square
The Inn at Court Square is a 4-star boutique hotel located right near the Downtown Mall. This quaint inn was constructed in the federal style of the time in 1785 and is now the oldest existing house in downtown Charlottesville! The Inn consists of two adjacent buildings housing a handful of guest rooms and suites, so you can be sure your stay will be intimate. Enjoy the southern-inspired breakfast before a full day of exploring!
Where to eat
Farm Bell Kitchen: Talk about the BEST BRUNCH I think I’ve ever had. I wisely split 2 entrees with a friend: a sweet and a savory. The bananas foster french toast was to die for and everything else looked equally delicious.
MarieBette Café and Bakery: If you love pastries (who doesn’t?), you’ll want to grab breakfast or lunch at MarieBette Café. You can get baguette sandwiches or your classic French pastries.
Bodo’s Bagel: Every town needs a great bagel place, and Bodo’s is it. You can’t get your bagels toasted here but they’re so fresh and perfectly baked you won’t even need them toasted!
Asado: Margaritas the size of your head? Yes, please! They also have a good assortment of traditional-with-a-twist Mexican dishes as well. It’s right in The Corner so you can also walk to bars and other attractions near UVA after you eat.
Riverside Lunch: For over 85 years, Riverside Lunch has been serving famous “smash” burgers. With a restaurant with that kind of history, you know it’s good! Stick with the classic double cheeseburger for a surefire crowd pleaser.
Blue Mountain Brewery: Blue Mountain Brewery is about 30 minutes outside of Charlottesville, but well worth the trip! We visited a few times when my husband was in school at JMU. Beautiful views, good food, and good beer. What else could you need?!
Maya: Check out Maya for some unique Southern and French inspired food. You can find everything from pan seared trout to Hanger steak to pimento cheese fritters.
The Alley Light: Shared. Plates. Need I say more? Okay, maybe I should say a little more in case you aren’t a diehard fan of shred plates like me. This French-inspired menu will allow you to taste a lot of classic French dishes with a Charlottesville twist and a delicious wine to go with it.
C&O: C&O is the perfect place to go if you’re looking for an upscale meal. You’ll enjoy a seasonal menu with a French twist by a renowned chef.
Marigold: Marigold is actually on Keswick Hall’s property and I have all ideas this stunning hotel doesn’t stop at just beautiful rooms. The chef is known around the world for being fabulous. You’ll experience produce grown right on the property along with other Asian-inspired fare at Marigold.
What to do in Charlottesville, VA
Explore UVA and The Corner
The University of Virginia is in the heart of Charlottesville. UVA is Thomas Jefferson’s creation and is full of beautiful architecture and history. The fall is the best time to go, because the leaves make everything look very magical and collegiate.
Walk around historic downtown
I always thought the area around campus was downtown but it turns out there’s actually another historic downtown area! Here you’ll find a “mall” that is brick paved and lined with shops and restaurants.
Seated in the middle of Virginia’s Appalachian mountains, there is an abundance of beautiful hikes around Charlottesville. Humpback Rocks Trail is one of the most popular hikes in the area! The rocks at the end of the trail are iconic, so be sure to snap a pic for Instagram.
You’re also located right near the Blue Ridge Parkway and Skyline Drive, so hop over to AllTrails to find the best hike for your experience and time!
We went to 3 different wineries and I would recommend them all! There’s more than a handful of wineries around the Charlottesville area on the Monticello Wine Trail so you’ll have to do a little research to see what you’re looking for and pick from there. We knew we didn’t want to drive far between each so we choose that way.
Here are a few recommendations:
Blenheim Vineyards: This is Dave Matthews’ winery! During Covid restrictions, you do need to make reservations for a picnic table ahead of time. The views were beautiful and the wine was my favorite of the day.
Jefferson Vineyard: A much smaller vineyard, but it has a great view of a mountain in front of you.
King Family Vineyard : King Family Vineyard is absolutely gorgeous. It has horse stables, tons of open space, and beautiful buildings on the grounds. On Sundays, they even have polo matches!
Other notable wineries: Veritas | Afton Mountain | Pippin Hill
Charlottesville is home to some incredible shopping, no matter what your style. Of course, there’s your traditional shopping malls but don’t worry, I’m not going to send you there. The downtown mall (not a strip mall, but a pedestrian of shops and restaurants) is the perfect place to support a family-owned business and grab a cute outfit from a boutique or a souvenir. Close to the downtown mall, you’ll find even more shops on West Main Street. Venture just outside of Charlottesville to the Crozet Artisan Depot or the Monticello Artisan Trail for something truly unique. On Saturday mornings, you can also enjoy the Charlottesville City Market or Farmers Market at IX Art Park.
The Monticello is Thomas Jefferson’s home is located just outside of Charlottesville. If you’re a history buff, you’ll certainly want to buy tickets to learn more about Jefferson, his life, and his legacy. It is recommended to buy tickets in advance. You can opt for a guided tour or self-guide throughout the house.
Just across the way from the Monticello is James Monroe’s Highland home. Similar to the Monticello, you can buy tickets and walk around the grounds to learn about our 6th president and the grounds he owned.
Shenandoah National Park
Charlottesville has a beautiful national park right in its backyard! Less than an hour from Charlottesville, you can spend the day just driving through the park or get out and explore one of the many hiking trails Shenandoah National Park has to offer.
If you’re willing to drive a bit further, you can see one of Virginia’s unique spots. The Luray Caverns is actually just a cave that was discovered in the 1800s and is now one of the most visited caves on the east coast! It’s about 1 hour 20 minutes from Charlottesville and would make a good stop to pair with a visit to Shenandoah National Park.
Charlottesville Weekend Itinerary
On your first day in Charlottesville, go ahead and check into the beautiful Keswick Hall or The Inn at Court Square if you want to be closer to the action. Explore the hotel and drop your bags then head off to the Downtown Mall.
Stroll around the mall and pop into shops to your heart’s content. Then, head to dinner at The Alley Light right in the downtown mall! Reservations are recommended. What better way to start your trip than with shared plates amongst your group?
After dinner, if the weather is nice head to Zocalo on Main St. for cocktails on the patio. Not up for a patio? Head to Tavern & Grocery for a classic cocktail.
I love to get in a little movement when I’m on a weekend trip (helps with all the food and imbibing!). Drive or walk over to the University of Virginia and the Corner to enjoy an early morning stroll. You’ll be done just in time for brunch at Farm Bell Kitchen!
After brunch, stop by the Charlottesville Farmer’s Market or head on out to Crozet to enjoy the Crozet Artisan Market.
When you’ve shopped to your heart’s content, hop in the car or hire a driver because it’s time to explore some of Charlottesville’s amazing wineries! My recommendation is to pick just two or three that are relatively close together. Blenheim, Jefferson, and King Family were all a reasonable distance apart. Just check out the Monticello Wine Trail map to create your own winery tour. Of course, you can always hire a guide if you don’t want to DIY.
Wining all day certainly works up an appetite, so head back to Keswick Hall for dinner at the bespoke Marigold. If you prefer to head back downtown, check out Maya to get your Southern food fix.
Still have some gas in the tank to keep exploring, grab a beer at the local Champion Brewing.
Sadly it’s already time to check out of the hotel. But don’t worry, your final day in Charlottesville is just beginning!
Once you check out, grab breakfast at Bodo’s Bagel. It’s an institution in Charlottesville and you can’t visit without getting their famous fresh bagels. After you fuel up with bagels and coffee, hop in the car and head into the mountains to go hiking.
Whether you want to head all the way into Shenandoah National Park or stick a little closer to town, there’s hundreds of great hiking trails to experience right near Charlottesville. Hawksbill is a rather popular hike within Shenandoah National Park and Rugged Mountain is a great choice closer to Charlottesville.
After your hike, grab lunch or a snack and head back home! I have a feeling you’ll be back to Charlottesville soon 🙂
Final thoughts on Charlottesville weekend itinerary
Charlottesville is a charming university town situated perfectly between history, wine, and some epic hiking. C’Ville, as it’s lovingly known, is great for a weekend getaway. No matter how you choose to spend your time, you will be itching to come back for another holiday! Be sure you check out this article for where to stay, where to eat, and what to do… or just take the amazing Charlottesville weekend itinerary planned for your here!
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