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About Charlottesville
Charlottesville is located under the breathtaking Blue Ridge Mountains. Much of the area is characterized by dense forests and rolling hills.
With so much natural beauty, it’s no wonder that Charlottesville was a magnet for our founding fathers, sitting 100 miles south of Washington, D.C. Charlottesville was home to both Thomas Jefferson and James Madison. Charlottesville was a retreat for these two former friends and Presidents. Here, many discussions took place about how to shape the government that we have today in the United States.
But natural beauty was not the only attractive aspect about Charlottesville. It was also the rich soil and the agricultural opportunities that drew Jefferson and Madison to settle there. Today, Charlottesville and the surrounding Albemarle County still have a thriving agricultural community. Many orchards and small farms around the area raise organic crops and free-range livestock.
My personal favorite crop grown in Charlottesville are the grapes! For over 200 years, the region has been producing some of the most awarded wines on the east coast. The area’s unique terroir produces grapes that are particularly spectacular for Viogniers and Cabernet Francs, in my opinion!
Though steeped in tradition, Charlottesville has evolved with the times. Charlottesville (a.k.a. C’Ville) offers visitors creative, modern cuisine as well as an impressive music scene. Whether catching a free concert at the Charlottesville Pavilion or dining al fresco along the Downtown Mall, it’s easy to sense the vibrancy of this destination.
When to Visit Charlottesville
The most pleasant months to visit Charlottesville, VA are between May and July with average highs ranging from 76°F to 88°F. Spring is also a lovely time to visit. I visited Charlottesville in August - it was definitely more hot and humid and had occasional scattered thunderstorms while I was there, so I would say that August is not the best time to visit. But the rain and humidity didn’t stop me from having a great time, so don’t let that deter you.
If you’re a fan of wine like me, you may want to consider visiting Charlottesville in the springtime when wine festivals are in full swing. Alternatively, fall has some wine festivals too, and the fall foliage is beautiful in Charlottesville.
It’s also important to note that students will flood back to the University of Virginia in the fall, so if you’re looking for fewer crowds, the summer months are better.
Winters are pretty chilly, so it wouldn’t be my personal favorite time to visit, however you will see better airfare/hotel rates during that time.
How to Get to Charlottesville
Charlottesville has their own small airport Charlottesville-Albemarle Airport (CHO), however I’d caution you to fly in and out of this particular airport as it’s been known to have delays. I flew directly from DFW into CHO, connecting in Charlotte (CLT). Although my arrival was smooth, a thunderstorm delayed my departure flight out of CHO, which caused me to miss my Charlotte flight. I got home 6+ hours later than expected, making for a very long day.
To avoid potential delays, you may want to consider flying into Washington Dulles (IAD) in Northern Virginia then taking a bus or train. Megabus heads to Charlottesville from IAD once a day - tickets are approximately $9-$24 and takes 2 hours and 35 minutes. Greyhound Bus is also an option. Amtrak operates a train 3 times a day from Alexandria to Charlottesville - tickets are approximately $28-$40 and take about 2 hours.
Other nearby airports include:
Richmond (RIC) - bus ride is approximately $29-$40 and takes 3 hours
Roanoke (ROA) - train ride is approximately $19-99 and takes 4 hours
Reagan Washington (DCA) - train ride is approximately $16-$93 and takes ~3 hours
Where to Stay in Charlottesville
My aunt and uncle live in Charlottesville, so they kindly hosted me while I was visiting, but there are some beautiful hotels and B&Bs that I would gladly stay at in the future if the opportunity presented itself. Here are some places that I researched that I believe would make for lovely stays.
Image courtesy of Boar’s Head Resort.
Boar’s Head Resort
The beautiful rooms seamlessly blend contemporary and antique décor. The property features a racquet and fitness club, an 18-hole golf course, indoor/outdoor tennis courts, 3 pools (1 is adults-only), and spa.
Image courtesy of Oakhurst Inn.
Oakhurst Inn
Set across 3 separate residences, the 36 elegant rooms offer modern luxury with historic charm. In addition to the bistro serving breakfast and lunch, there are 4 onsite libraries and a bar that serves artisanal coffees and cocktails.
Image courtesy of Keswick Hall.
Keswick Hall
The 4-star hotel features 80 newly refreshed guestrooms as well as an 18-hole golf course, spa, tennis courts, fitness center, and three pools. Turndown service includes a serving of Keswick Hall’s handcrafted chocolates and there is a fine dining restaurant onsite.
Image courtesy of The Clifton.
The Clifton
This white-painted mansion is near the historic Michie Tavern. Rooms are tastefully decorated with antique furnishings as well as modern luxuries. Continental breakfast and afternoon tea are complimentary on the veranda. The property also features an elegant restaurant, an outdoor pool, a hot tub, and a croquet lawn.
Image courtesy of The Draftsman.
The Draftsman
The guestrooms and lounge area feature sophisticated, modern décor and refined Southern charm.
Image courtesy of Quirk Hotel.
Quirk Hotel
This Hyatt-owned boutique art hotel has Instagram-worthy photo opportunities everywhere you look.
Styled in minimalist contemporary design, Quirk once served as a downtown department store circa 1916. The ambiance is on-point with design features like period hardwood floors, contemporary artwork, recycled furniture, and vaulted ceilings. If you don’t stay here overnight, at least make sure to visit the rooftop bar and try a “local selection” drink like the Pink Breeze.
What to Do in Charlottesville
Downtown Mall
Yes there are shops and restaurants, but it’s nothing like your typical shopping mall. The streets are alive with local performers, delicious food, and echoes of music. I lost count of how many shops and restaurants there were within this district. The free trolley service connecting the Downtown mall to the University of Virginia along West Main Street, is a helpful convenience.
A few interesting shops you may want to visit:
Cocoa & Spice - family-owned chocolate shop, with unique flavor combinations like White Chocolate Pistachio & Pink Peppercorn, Cajun Bark, & Beer Toffee Pretzel Bark
The Glass Palette - interactive glass art studio
Blue Whale Books - used and rare bookstore
BitterSweet - boutique clothing and accessories store
There are literally SO MANY restaurants to choose from on the Downtown Mall...here are a few I’d recommend:
Hamilton’s at First & Main - contemporary gourmet American cuisine
Petite Mariebette - bakery & coffeehouse
Fleurie - modern French dinner spot with an extensive wine list
Sultan Kebab - authentic Turkish food
C & O Restaurant - charming old building with a menu that changes monthly
Charlottesville Pavilion
At the end of the Downtown Mall sits the Charlottesville Pavilion (aka Ting Pavilion). It’s an outdoor venue for live performances featuring premium seating, a spacious lawn, and a professional stage house.
When I visited, a Fridays After Five concert was going on. This concert series features regional bands with a wide range of musical styles, from rock and blues to salsa and reggae. This free community concert series is in its 33rd season.
Freedom of Speech Wall
In commemoration of Thomas Jefferson signing the Declaration of Independence in 1776, Charlottesville erected the Freedom of Speech Wall in the Downtown Mall, where visitors can write their own expressions of life, liberty, and the pursuit of happiness. The wall is a dark granite slab covered in scribbles from locals and tourists, all expressing themselves through art and declarations. Add yours to the wall when you visit!
Wine Tasting
As I mentioned earlier, there is no shortage of vineyards in Virginia. Because of the rich soil, Charlottesville is home to many small farms, orchards, and vineyards. For over 200 years, the region has been producing some of the most awarded wines on the east coast. There are more than 40 wineries within a 25-mile radius of Charlottesville - they are all part of the Monticello Wine Trail. (Visit their website to put together your own custom itinerary.)
You literally could spend days and days plotting along this wine trail, but here are the three favorite places that I visited. I liked these three because they offered more than just amazing wine with historic sights, beautiful views, and onsite activities.
Jefferson Vineyards
They are considered one of the best and most popular wine producers in the area, conveniently located at the foothills of Monticello.
The Jefferson estate was the site of Virginia’s first wine company and commercial vineyard. Today, their award-winning wines include both delicate and refreshing white wines to elegant, full-bodied reds. To my surprise, my favorite was the Vin Blanc 2018 - it’s a semi sweet white wine with notes of melon and grilled pineapple. It was a hot day, so this wine was perfect for the summer. Another crowd favorite is their Viognier 2019, which has won 4 gold medals. (Charlottesville in general produces beautiful Viogniers, if you’re a fan of this white wine.)
Due to COVID, the winery has made some changes, which may continue for the foreseeable future. Instead of tasting wines inside the tasting room, the entire operation has moved outdoors. You can select a flight or wine then take it out to one of three various sitting areas - a garden setting, a casual picnic table setting under a tent, or my personal favorite, at some shaded tables on the lawn overlooking the vineyards.
King Family Vineyards / Roseland Polo Games
Not only are their wines and grounds beautiful, but they also have a full horse stable, polo school and polo field on the grounds. This may have been my favorite activity during my entire time in Charlottesville - what’s more fun than getting dressed up to tailgate and watch ponies, right?!
The Roseland Polo Club hosts matches on Sundays - they completely free to watch! The vineyard just asks that you purchase their wine onsite. The best way to enjoy a Sunday at King Family is to arrive early around 10:30-11:00 a.m. before the 12:00 p.m. polo game. Pull your car right up to the field and set up your tailgate with a tent and chairs. We brought picnic snacks to enjoy with our King Family wine.
If you can’t visit on a Sunday during May through October, King Family Vineyard is still worth the visit for both the wine and the views. The vineyards are located in Crozet, 15 minutes away from Charlottesville at the foot of the Blue Ridge Mountains. There’s a covered veranda and brick patio for outdoor picnics and an indoor Tasting Room with a stone fireplace.
A fan favorite here is the Crosé (a rosé that’s playfully named after their small town Crozet). My personal favorite at this particular winery was the Viognier 2020 with citrus, honeysuckle, and white peach notes.
Barboursville Vineyards / Barboursville Ruins
Although this winery is technically 30 minutes outside of Charlottesville, it’s worth the visit. This winery is set on an 18th century estate which still has the remnants of the Barboursville Ruins on display.
Barboursville Vineyards have several tasting options. The most casual setting is the Discovery Tasting Room - this is where we decided to do our tastings. Due to the pandemic, Barboursville Vineyards invested in high-tech wine dispensary machines. Guests are given a card with 6 credits and then they can go around the different Winestations set at the ideal temperature for each wine and press a button to try a one ounce pour. Though it meant less time with the staff, I found the experience to be novel and fun - something different than other tasting room experiences. My favorite here was the Cabernet Franc Reserve 2019 - I loved it so much that I bought 6 bottles of it!!
If you still would like a more intense tasting experience, you can go to the Library 1821 on the grounds. In this location, the winery presents a changing selection of flights of current and older vintages from their cellars, not just current vintages. With these flights, you also receive bite-sized culinary pairings.
After your tasting, stroll over to the Barboursville Ruins, one of Jefferson’s architectural masterpieces. Surrounded by large boxwood gardens, the Landmark Ruins are what’s left of the brick mansion that Jefferson designed for Governor James Barbour. Finished in 1822, the home had 8-rooms and an octagonal drawing room (which Jefferson was so fond of). On Christmas Day in 1884, everything but the brick walls, masonry partitions, and grand fluted columns were destroyed by fire. Though you cannot walk inside of the ruins, you are free to get a 360° view of what’s left of this home.
Pippin Hill Farm & Vineyards
The relaxed elegance of this winery makes it a hot spot for private parties, weddings, graduations, and more.
Because Pippin Hill is also a farm, this winery does a particularly good job of pairing their wines with delicious farm-to-table foods. Menu items include shared cheese plates, sliders, seasonal shared plates, appetizers, soups, and more.
On Fridays, they host Featured Farmer Fridays - a mini farmers market showcasing food from local farmers in the area.
Image courtesy of Pippin Hill Farm & Winery.
Brewery-Hopping
Though Charlottesville does not have as many breweries as wineries, they still have a wide range of places to choose from! The first brewery was founded in Charlottesville in 1987. Here are the breweries I visited while in the area.
South Street Brewery
In addition to a solid beer selection, South Street Brewery also has a delicious food menu with apps, sandwiches, entrees and more. My favorite was the Virginia Lager, a light amber lager. Satan’s Pony, a medium-bodied amber ale, is also a crowd favorite.
Three Notch’d
The downtown Charlottesville location that we visited is an interesting spot. Looking somewhat unassuming from the street, Three Notch’d actually sits within the IX Art Park. Upon arrival, you drive down the hill into their parking lot area. The IX Art Park is Virginia’s first and only immersive art space. It’s a public, non-commercial, interactive space for creative community gatherings.
Although this Three Notch’d location is not explicitly connected to this Art Park, it does serve for a unique setting. Upon entering Three Notch’d, you’re greeted with high ceilings, rows of long communal tables, and the sounds of Millennial throwbacks. They do have an outdoor patio but we opted to sit in the expansive interior warehouse portion of the brewery which was pleasantly air-conditioned. Like South Street Brewery, Three Notch’d offers a food menu with locally-sourced, beer-infused dishes designed to compliment the season as well as what’s on tap.
Blue Mountain Barrel House & Smokin’ Barrel Restaurant
Okay, so Blue Mountain Barrel House Brewery is technically well outside of Charlottesville, in Arrington, Virginia, however I enjoyed this place so much that I couldn’t leave it off this blog post. My aunt and uncle have a farm in the area, so that’s what brought us to this brewery. This brewery has stunning views of the Blue Ridge Mountains and serves as the region’s first rural brewery starting in 2007. For being a rural brewery, I’ll admit, my expectations were low, but this place ended up being my favorite brewery of them all that we visited!
I enjoyed their range of beers as well as their farm-to-table food. We enjoyed watching the sunset on the outdoor patio in lounge chairs that surrounded a fire pit. I also loved walking over to the hop crop in their field. It was my first time seeing hop plants growing out on the vine and I was surprised to learn that the vines grow on sturdy trellises. My favorite beer at this brewery was the Full Nelson, a flagship Virginia pale ale.
Carter Mountain Orchard
First of all, it was my first time visiting an orchard, and I’ve always wanted to. During the time I visited, apples were not in picking season yet but the peaches were. Unfortunately I didn’t have time to actually pick any fruit, but you do have the option to do so.
Carter Mountain Orchard is a divine place to soak in all the beautiful views of Charlottesville. The Orchard sits on a mountain (as implied by their name) and overlooks the city and valley below. The day I visited, it was actually rainy and the clouds were low and covering our view while we were up on the mountain. But I hoped to get that beautiful view so badly that I managed to make it up the mountain one more time on the day that I was leaving Charlottesville before I had to head to the airport. And luckily, that morning was sunny (and rather hot!) so I was able to get some amazing views from the Orchard before departing.
In addition to seeing the beautiful views, Carter Mountain Orchard has a market, bakery and country store. I enjoyed looking through the beautiful jams, honeys, and freshly-picked fruit/vegetable medleys on display for purchase at the market - they were so picturesque and colorful. The country store also had many adorable souvenirs and country mementos for the house. I tried peach cider from the market and it was amazing!! Another MUST-TRY from the bakery are the fresh apple cider donuts. Your visit to the Orchard is not complete without trying one of these delicious treats.
But here was my favorite aspect of the Orchard (aside from the view)...I was able to pair my fresh apple cider donut with a lovely flight of hard apple cider! Below the country store sits Bold Rock Hard Cider Tap Room, serving their entire cider portfolio. I tried their premium flight (off-dry, champagne, and premium ciders) because I don’t generally care for overly sweet ciders. It came with 2 champagne-style ciders (which I had never heard of before), a premium dry cider, and an IPA-style cider (also never heard of before). I honestly liked them all - the champagne-style is a great substitute for champagne or could be used in a mimosa, the premium dry is smooth and balanced, and the IPA-style was interesting, hoppy, and tasty!
University of Virginia
To my surprise, the University of Virginia was actually inspired by Thomas Jefferson. He wanted to reinvent higher education in the United States by creating an environment where students and faculty could learn from one another.
As a result of this desire, Jefferson founded UVA in 1819 and created the Academical Village - a masterpiece within it. The Academical Village, a UNESCO world heritage site, is a beautiful, scenic part of the UVA campus located on the central lawn. If you want to visit UVA, this is where I would recommend visiting. Jefferson designed the Village to be a place for cross-disciplinary exchange. Students live in single rooms between professors’ quarters. In the center stands the domed Rotunda (library).
Lawn rooms are highly coveted quarters reserved for accomplished fourth-year students. Most have fireplaces and a rocking chair, however they do not have air conditioning or connected bathrooms or laundry rooms. So, although it is an honor to be selected for a Lawn Room, I’m not sure I would’ve chosen to live in those particular rooms!!
Today, the University of Virginia welcomes over 17,000 students each year on its 1,682 acres.
Shenandoah National Park
Although I love hiking, this was one activity that I unfortunately didn’t have time for.
Trails feature cascading waterfalls, fields of wildflowers, and vibrant animal life, such as deer, songbirds, and black bears. In addition to hiking, visitors can camp, bike, and horseback ride in the park.
If you don’t have much time to hike, you can drive along Skyline Drive, a 105-mile road that winds along the crest of the mountains, so that you can get landscape views of the park.
A single vehicle pass for 7 consecutive days is $30 and entry for walk-up visitors is $15.
Monticello
Jefferson inherited the plantation land from his father when he was 26 years old. Over the next 40 years, Jefferson designed and redesigned the mansion. Monticello is beautiful and worth the visit even if you’re not a history buff. The property is well maintained and really shines a light on how life was back in the 1700s.
When you drive to Monticello, you arrive at the base of the property where there is a small museum, gift shop, and bathrooms. If you have the time, it’s worth your time to watch the 10 minute video inside the museum to get a good background on the property and Jefferson’s history. I learned from the video that Thomas Jefferson was only 33 years old when he drafted the Declaration of Independence. I’m 33 years old right now. Jefferson was no perfect man by any means, but I did respect the fact that he could draft such an important document at such a young age...I certainly don’t know if I would have been up to the task!
After the self-led brief museum tour, you can show your tickets and ascend the steps up to the waiting area for the small bus that will take you up to the plantation home. You are free to walk the grounds and explore the gardens but your tickets are what will allow you access to the house. Due to COVID, the tours are now self-led via QR code on your phone, however I actually liked this because I was able to tour the house at my own pace.
One of my favorite things to see in the house was a wine pulley system that Jefferson developed. The pulley system was built into the fireplace of the dining room. It connected down into the wine cellar of the property. Someone from the wine cellar could put a bottle of wine onto the pulley then it could be shimmied up the system into the dining room for quicker serving.
Although Jefferson’s life and home design were impressive, Jefferson was not without great fault. Jefferson had over 600 enslaved people work on his plantation over his lifetime. I felt that the tour does a good job of telling the stories of the enslaved people on property as well as Sally Hemings (Jefferson’s biracial enslaved mistress and mother of 6 of his children). The tour outlines how life actually was on the property without any sugar coating.
On your way back down the mountain, either via complimentary shuttle or walking, you can see a gravesite on the property where Jefferson was buried.
If you pick one historical activity to do during your time in Charlottesville, tour Monticello. Jefferson and Charlottesville history go hand-in-hand, so it’s the best way to get a sense of the destination’s origins.
Montpelier
It’s about a 45-minute to 1 hour drive from Charlottesville.
You can get a property pass and enjoy the 2,700 acres of grounds, trails, and the Annie duPont Formal Garden (my favorite place). Alternatively you can purchase a ticket for the Highlights of Montpelier Tour ($35), which will allow you to access inside of the house. Tours are guided - if I remember correctly our tour was about 1 hour. I actually would have preferred a shorter, self guided tour, but our tour guide was knowledgeable so I did learn more about the Madisons and their property than I would have just going through solo.
James and Dolley were an interesting couple - they were very much in love but opposites in many ways. James was more introverted, studious, and short in stature while Dolley was social, charming, and tall. The two never had children but Dolley did bring her son, Payne, into the marriage after being widowed in her first marriage.
Like Jefferson, Madison regrettably had over one hundred enslaved people working on his tobacco plantation. There are accounts of Madison actually arguing that slavery was incompatible with Revolutionary principles, but it’s believed that his financial situation always dissuaded him from ending slavery on his land. Madison did not free a single enslaved person in his lifetime. The stories of enslaved people on the Montpelier property were highlighted throughout the tour and plantation so as to give a complete picture of what life was like at that time.
Michie Tavern
They serve an all-you-can-eat lunch from 11:30 A.M. - 3:00 P.M. with a set menu full of Southern comfort food favorites like, southern fried chicken, marinated baked chicken, history-smoked pork barbecue, stewed tomatoes, black-eyed peas, buttermilk biscuits, and more. Servers are dressed in period attire to help bring your historic lunch to life.
Michie Tavern is near Monticello so if you’re looking to make a day of it, I recommend touring Monticello in the morning, eating at Michie Tavern for lunch, and heading over to Jefferson Vineyards for wine tasting afterwards.
If you’re visiting on a weekend, the 1784 Pub on site is open on Friday and Saturday from 3:30 P.M. to 7:00 A.M. It’s an 18th century style pub serving local wines, beers, and hard ciders with light snacks. You can enjoy your libations in the Tap Bar Room fashioned after the original Michie Tavern, in the antique-filled Public Room to play 18th century games, or outside on the Front Porch in a rocking chair overlooking the Blue Ridge Mountains.
Antique Shopping
My aunt and uncle who live in Charlottesville are avid collectors of antiques, especially from the Civil War era. Much of their home décor and furnishings are actually antiques; every item in their house holds an interesting story.
If you enjoy antiques and antique shopping, Charlottesville is a really great place to do this due to how much history lies within the town. We did a little antique shopping one morning, and to my surprise, I loved it! It felt like I was hunting for treasures and stepping back in time to do so.
While there, I found a beautiful crystal and gold vintage perfume bottle, and it now sits on my vanity as a beautiful memento of my trip! My other favorite find was a beautiful old piece of Louis Vuitton luggage! I was tempted to buy it but in reality, it was too delicate for use and would have just been put on display, so I decided to pass.
If you’ve got a tight schedule, there are some antique shops in downtown Charlottesville that you can visit instead, including: Circa, Patina Antiques, Etc., Low Vintage Clothing, and Oyster House Antiques.
Closing Thoughts About Charlottesville, Virginia
Well...there you have it! My guide on how to spend the perfect weekend in Charlottesville, Virginia.
Charlottesville is a beautiful place nestled under the Blue Ridge Mountains, full of historical sites, award-winning wines, and tasty restaurants. It’s a place that offers you continuous opportunities to reconnect with nature. The scenic rolling hills, forest trails, and blue hued mountains make a perfect backdrop for solo travel, couples travel, or a girls getaway.
Although I absolutely loved my summertime visit and wouldn’t change a thing, I would love to come back and visit in the fall to see the colorful, crisp leaves and enjoy a warm fireplace in the evening with a glass of Cab Franc in hand!
It’s easy to see why my aunt and uncle retired in Charlottesville, Virginia - there’s so much to love about this charming destination!
author bio
Known as The Jet Set Blonde, Brittany Ryan inspires others to add more adventure to their childfree travel experiences. Brittany has visited 23 countries (and counting!) Connect with her to get access to detailed childfree travel itineraries, travel guides for weekend getaways, and updates on adult-only hotels, resorts, cruises, and other travel amenities.
