For a city of less than 45,000 residents, Charlottesville certainly punches above its weight when it comes to what it offers visitors. As first-timers to the city, Henk and I didn’t know what to expect in terms of attractions or cultural points of interest. We only knew it would be our jumping off point for exploring more of this part of the state. Needless to say, we were more than pleasantly surprised to discover all of the decidedly grownup things to do in Charlottesville, Virginia, from craft cideries and wineries to quirky art installations and UNESCO World Heritage Sites. And because this place is also home to the University of Virginia, there’s a youthful buzz to this city that infuses it with life and even attracts celebrities like John Cleese (more on that later!).

Here then, are some of the highlights you don’t want to miss when visiting Charlottesville, Virginia.

1. Visit Monticello: the Home of Thomas Jefferson

You can’t swing a cat in Virginia without hitting something of major American historical significance, whether it’s a Civil War battleground site, or the home of America’s First President. It’s just that storied of a place, and Charlottesville is no exception: less than two miles from downtown in Albemarle County you’ll find the area’s historical crown jewel, Monticello, the hilltop home of Thomas Jefferson.

Jefferson made his mark in history as the principal author of the Declaration of Independence and the third President of the United States, and visiting this landmark is without a doubt one of the most popular things to do in Charlottesville. It also gave us the opportunity to learn more about Jefferson as a person and the legacy he left not just America, but Charlottesville itself. Read about our visit to Monticello in more detail here.

2. Tour the University of Virginia

We’ve listed Monticello first in this itinerary, not just because it’s one of the best things to do in Charlottesville but because it provides good context before visiting the University of Virginia which is located here. Understanding more about Thomas Jefferson’s passion for architecture will help you appreciate this campus, which he designed and has been lauded as a masterpiece and his greatest architectural achievement. Plus, together with Monticello, these two properties have been designated a UNESCO World Heritage Site because of their cultural and historical significance.

Jefferson actually took on the task of designing the University of Virginia at the age of 79, in what he described as the “hobby of my old age”. (Talk about a second act!) He incorporated his love of classical architecture into the layout and buildings, with a nod to Rome’s Pantheon in his design for the central library, the Rotunda.

Setting a library at the centre of his campus may not seem so revolutionary today, but Jefferson believed in the separation of Church and Education, so he chose to make the Rotunda the centrepiece of his campus, not a church, which was the norm for most other universities in his day.

An ‘Academical Village’

Jefferson believed that knowledge was better fostered if professors and students had greater access to each other. So for the University of Virginia campus he designed what he called an ‘academical village’ where both educators and students would live on-site, giving them more opportunities to interact with each other. This concept came to life in pavilion-style apartments and dorms connected by pillared porticoes that flanked an open space known as the Lawn, at one end of which is the Rotunda.

To this day, professors and students live alongside each other and the Lawn dorm rooms are very covetable and only available to highly accomplished 4th year students. They are so desirable that students don’t seem to care that the rooms don’t have bathrooms and that they need to physically go outside to access washroom facilities (which can’t be much fun in the winter!)

FUN FACT: Famous alumni of the University of Virginia include journalist Katie Couric and comedienne Tina Fey.

Highlights of the University of Virginia Campus

As you stroll the UVA campus, fans of Edgar Allan Poe won’t want to miss viewing his dorm room, which is kept as it would have looked when Poe was a student here. Even though Poe only attended the University for one session, his room is maintained as an historical exhibit by a student group known as the Raven Society, one of the not-so-secret secret organizations on campus, of which there are many.

The Rotunda is open to visitors as well as students, and worth going inside, if only to see the design of the space from the inside as well as the outside. (Jefferson clearly loved domes as he designed Monticello with one as well.)

Jefferson also designed a serpentine style of brick wall, a novel approach that was more efficient because it used less bricks than a traditional straight wall, while creating a more aesthetically pleasing, organic division of the gardens and buildings on campus. Many of those gardens are also open to visitors, so take a moment to admire them as well.

A more recent addition to the university campus is the Memorial to Enslaved Laborers, a permanent tribute to the people who built the University, and a reflective place that is meant to be as contemplative as it is revelatory, with inscriptions that describe the many injustices faced by the Black Americans who worked here.

TIP: The University of Virginia offers daily historical tours when courses are in session. Check their website for more details and timing.

3. Hang at the Downtown Mall in Charlottesville

Stepping out of the UNESCO-recognized historical legacy left by Jefferson in Charlottesville, it’s time to step out and explore modern day CVille, as its known to locals. Start with the Downtown Mall, one of the longest pedestrian malls in the United States, and home to more than 120 shops and 30 restaurants.

Simply put, this is the jewel of historic downtown CVille and one of the most attractive commercial destinations you’re likely to find in any city of this size (or any size, period). With a vibe that is part Main Street, part village square, this has almost a European feel with its expansive tree-lined cobblestoned centre ‘aisle’ of patios and open-air cafes, sandwiched between local boutiques and restaurants.

There are independent bookstores (check out the Blue Whale which also sells antique prints and maps), luxury consignment shops like Agents in Style, decor stores, pubs, restaurants, pastry shops and for the performing arts, there is the historic Paramount Theatre.

Visit the Downtown Mall at night when the overhead lights come on, adding a little more magic to the atmosphere, and you’ll see why this place is really something special.

4. Get Inspired at IX Art Park

Not far from the Downtown Mall, but still right in the centre of town, you’ll find CVille’s IX Art Park, a repurposed ex-industrial area that has been converted into a community gathering space designed to inspire and encourage creativity.

This area is large and incorporates a permanent outdoor mural and sculpture park that is managed by the IX Foundation, a not-for-profit that also runs and curates the installations and activities here.

These include collaborative mural painting, free community art classes and events, and even a Farmers Market/Crafts Market every Saturday that brings together 60 artisans, local vendors and food purveyors.

TIP: These #LoveVA art installations can be found all around the state and each one is unique. Click here for a complete list of their locations.

The centrepiece of the IX Art Park has to be the Looking Glass, the first immersive art experience of its kind in Virginia. One of the founders who conceived of the idea had seen an interactive installation by the company Meow Wolf, and was inspired to bring something similar to Charlottesville.

Utilizing a defunct warehouse space that used to be a silk factory for manufacturing parachutes, the Looking Glass space is both an art installation and a bar/music venue. Enter one half of the space and you enter a world of fantasy, with Alice-in-Wonderland style art installations that are both tactile and interactive.

Visitors of all ages are encouraged to become part of the art, by entering kaleidoscopic funhouse rooms or hobbit-sized forest dwellings, or just lounging on giant fuzzy caterpillar couches.

And with local artists contributing different pieces every year, the experience is constantly evolving and changing.

On the other side of the warehouse space, grownups have access to Frank’s Peculiar, a bar/event space that continues the psychedelic vibe with funky decor and blacklit-painted nooks and crannies.

When the bar isn’t showcasing local musicians on the stage, patrons can contribute to the sketchbook on the bar, all while sipping a cocktail or swinging – literally – to the beat (there’s an actual swing inside!).

The best part: all proceeds go to supporting the non-profit foundation and the community of Charlottesville.

5. Drink in Craft Ciders and Amazing Views at Carter’s Orchard

When it’s time for an adult beverage, why not combine it with a spectacular view? Virginia is about as forested and green as it gets (or as Henk remarked, “it’s so green the trees have trees on them!”), and there’s no better place to enjoy that lush panorama than from the Carter Mountain Orchard high atop a ridge in Albermarle County about 15 minutes’ drive from Charlottesville.

The Carter Mountain Orchard is a family-run fruit business that has been in operation in Charlottesville for more than 100 years. The family purchased the hilltop orchard property in 1985 and since then it has become a destination for locals and visitors alike, where you can purchase fresh fruit and other produce (Carters is known for its peaches and apples especially), or indulge in some of their famous apple cider donuts. (we did and we can definitely recommend them).

They also have begun making their own Carter Mountain Wines and operate a tasting room on the mountain where visitors can purchase wine by the glass or bottle, or sample several vintages with a tasting flight. If cider is more your thing, there’s also a seasonal Tap Room where they serve a selection of locally crafted Bold Rock hard ciders.

Grab a flight, then head to one of the outdoor picnic tables where you can enjoy your beverage of choice while drinking in one of the best views in the area.

6. Sip in Style at the Quirk Hotel’s Rooftop Terrace

And speaking of adult beverages….if you would like some elevated cocktails to go with an elevated experience, head up to the rooftop of Charlottesville’s Quirk Hotel. First of all, any hotel that defines itself with the word ‘quirk’ has my complete attention, but when it comes with a stunning rooftop terrace to complement the hotel’s funky, minimalist interior design aesthetic, I am all in.

Henk and I were visiting in late April which may be early for outdoor patios in Toronto, but being a little farther south meant that the weather in CVille was absolutely perfect for enjoying a late afternoon drink al fresco. The wraparound rooftop did not disappoint, not only giving us great views over the streets of Charlottesville and the surrounding hills (Carter’s Orchard viewpoint included), but the cocktails on offer were as elevated as the venue.

CVille + John Cleese

While we were enjoying Quirk’s rootop (and some delicious alcoholic concoction I cannot remember the name of), we started chatting with another local couple who were enjoying a drink beside us. Originally from Minnesota, Patrick and Jane were globe-trotting nomads for most of their youth until they decide to look for a place to plant some roots about 25 years ago. What was interesting was that after all the countries and cities they had visited in the States and abroad, they absolutely fell in love with Charlottesville for the same reasons we were discovering: this was a city that may seem small in population, but is big on culture, attractions and lifestyle.

It was then that Patrick mentioned John Cleese. Yes, that John Cleese of Monty Python fame, who Patrick actually texts quite regularly and vice-versa (Pat described Cleese as his very polite stalker!).

What could bring John Cleese to Charlottesville, was of course, my question. It turns out that both Patrick and Cleese are keenly involved in the research that the University is doing into the nature of human consciousness and Cleese has been here on numerous occasions to assist in fundraising events.

So it would seem that Tina Fey is not the only comedian who has a connection to Charlottesville. Funny, that.

A Grownup Getaway in Charlottesville, Virginia

CVille may be a university town, but when it comes to the variety of things to do in Charlottesville that appeal to our demographic, Henk and I were surprised to discover how much this city offers visitors. Its creative attractions, diverse restaurants and Downtown Mall give the city an urbane vibe, and for history buffs or culture vultures there’s enough options to fill several days. It is definitely worth spending some time in Charlottesville, whether it’s as a short weekend detour off the north/south snowbird route to Florida, or as a destination in its own right that makes for a perfect grownup getaway.

And if you’re lucky, you might even bump into John Cleese as you are strolling Charlottesville’s streets – wouldn’t that be a brag-worthy story to post to the Gram!

GETTING TO CHARLOTTESVILLE

Charlottesville does have its own international airport as does Richmond, Virginia, which is about an hour’s drive from CVille. The largest major international airport near Charlottesville is Dulles, in Washington DC. From there, it’s about a 2 and a half hour drive.

WHERE TO DINE IN CHARLOTTESVILLE

QUICK BREAKFAST: Petite MarieBette
This tiny cafe is the perfect choice to grab a coffee and quick breakfast sandwich or delicious french pastry (think chocolate croissants, brioches and galettes) before heading out to see the sights.

DINER BREAKFAST: Blue Moon Diner
I’m still kicking myself that we didn’t make it here, and only got to peek in the window (Tuesday was our opportunity, and that’s the one day they are closed). This is exactly the type of local diner that I love, and the prices look as good as the nostalgic decor inside.

LUNCH: Michie Tavern, near Monticello
More than just an historic restaurant and former inn, the Michie Tavern (pronounced Mickey like the famous Mouse), is a Albemarle County institution and a must-do if you want to sample some authentic Virginia comfort food with a side of history.

Michie’s was originally an eating-and-meeting place located 17 miles away from its current location on what was the stagecoach route back in the late 1700s, when it no doubt played host to a few rebels and probably even more revolutionary debates. But once the railway arrived and diverted traffic elsewhere, Michie’s declined, trading hands multiple times until the late 1920s. It was then that an enterprising local woman saw its potential as a tourist museum and physically moved the tavern to its current location near Monticello.

Today, Michie’s is both museum and restaurant in the style of an ‘Ordinary’ (the 18th century term signifying the same food for the same price, every day). Enjoy a buffet-style selection of southern favourites: fried chicken that actually tastes like real chicken, green beans cooked and flavoured with cured Virginia ham chunks, stewed tomatoes, mashed potatoes with gravy, biscuits, corn bread and much more. If you need a refill, the attentive staff will save you the effort of lining up again and deliver you more of whatever you want, as much as you want, as many times as you want. So come hungry, but be sure to leave room for the traditional peach cobbler for dessert.

TIP: Michie’s is located about a half-mile from Monticello on the same road, so it’s a great place to stop either before or after your tour of the Jefferson estate.

INEXPENSIVE DINNER: Maru Korean in the Downtown Mall
Popular with the university crown, Maru’s is both affordable and flavourful, with a casual atmosphere and friendly service. BiBimBap is a popular classic here but there are other great options, all of which pair well with Korea’s best selling German pilsner, Kloud, which they serve here as well.

MID-PRICED FRENCH CUISINE: Café Frank in the Downtown Mall
For this recommendation, we relied on some local foodies who have followed this Chef from restaurant to restaurant as he built his Charlottesville career. He’s now opened up his own place where he is preparing the French cuisine he loves to serve.

HIGH END STEAK: Black Cow Chophouse: This steakhouse is at the upper end of the budget spectrum, but highly recommended by local foodies. The owners came from Public Fish & Oyster, another highly acclaimed restaurant in town that they established, so you can bet this will be equally upscale.

WHERE TO STAY IN CHARLOTTESVILLE

The Quirk Hotel
Apart from its amazing rooftop terrace and adjoining lounge, the Quirk hotel is everything you want in a boutique hotel: style, personality and all the comforts you don’t get at home! Meaning, an on-site art gallery showcasing works by both emerging and established artists; a curated boutique shop with stylish jewelry, clothing and decor; an on-site restaurant and separate cafe; valet parking and oh yes, modern, stylish rooms where someone else makes up the king-sized bed and straightens up after you.

Pink is the signature colour at the Quirk and you’ll find fun touches of it in all of the rooms (even pink-tinted shower glass!) and around the common areas and there is interesting artwork outside of the gallery space as well, adding to the eclectic decor of this hotel.

Location-wise, the Quirk couldn’t be better suited for exploring Charlottesville, as it is a short walk to the IX Art Park, the Downtown Mall, and the restaurants and stores along Main Street. (Watch a short video of the Quirk below)

Special thanks to Virginia Tourism who hosted Henk and I on our visit to Charlottesville.