13 Fabulous Charlottesville Experiences

Thomas Jefferson on a bicycle with Andy Warhol styling

We recommend the following 13 fabulous experiences in Charlottesville. Adventure awaits in any direction here. From bookish revelations and artful forays to excursions that require gait and stamina, here’s our list of 13 fabulous outings! In each case the backdrop is exquisite, from undulating mountains to classical architecture. Nearby to it all is the kitchen, vineyard, or pub where après-adventure can be savored and shared. Here’s our bucket list of wonderful experiences that await you!

1. Cool your Heels at The Wool Factory

Five years ago, one of Charlottesville’s most historic areas got a serious makeover. The Wool Factory, located just 1.7 miles down Market Street from the heart of downtown, is a hidden oasis of history and beauty, now a unique event venue replete with a brewery, coffee and wine tasting, and fine dining. Originally built in 1882, The Wool Factory now stands as a stunning example of 19th-century architecture, with its high ceilings, exposed brick walls, and original hardwood floors. The building overlooks the Rivanna River with easy access to hikes along the Rivanna Trail. This is a wonderful place to cool your heels!


2. Discover the Melodrama of The Raven Room

Calling all Edgar Allan Poe Fans! While he only studied at UVA for one year in 1826, before academic duress and gambling debts caused his Richmond patron to withdraw support, Poe’s dorm room – popularly known as The Raven Room — has been preserved and awaits your meek footsteps! These cramped quarters become still a scene of midnight initiations by elite and literary groups of students. The ominously numbered dorm 13 West Range displays period furniture, books, and Poe’s original bed. A button on the doorway unlocks an audio history you’ll swear was read by Vincent Price! 


3. Picnic Hikes the Blue Ridge

Our Blue Ridge is world-famous for day hiking.There’s no better way to enjoy an afternoon and catch a sunset. Hop on I-64 W and in 20 minutes you’ll be at the doorstep of both Shenandoah National Park ($30/vehicle annual pass) and the Blue Ridge Parkway (free). Here are 3 classics:

  1. Little Calf Mountain is the easiest hike in the park. Drive six miles into the park to Milepost 99.5, where you’ll find parking. This is an easy, family- and picnic-friendly, out-and-back hike that begins in a rolling, grassy meadow before climbing through a forest to the summit where you’ll find stunning views westward thru the Shenandoah Valley. The trail is just under 2 miles roundtrip, all along the white-signed Appalachian Trail, and is suitable for all ages and levels of experience. 
  1. Blackrock Summit at Milepost 84.4 is a short and sweet, one-mile circuit hike that takes you to a Wow moment in a huge talus field of big views that will transport you to a time when giants hurled boulders for sport. This is a crowd-pleasing excursion for families and romantics alike. Enjoy a picnic lunch or snack at the top of the hike and take in the beautiful views.
  1. Humpback Rocks is a very popular, two-mile out-and-back hike beginning at Milepost 5.8 on the Blue Ridge Parkway. The route is a gradual climb to massive outcroppings that afford 360-degree views that inspire reverence for our rugged mountain beauty.

4. Find the 5th Street Mosaic

Crane your neck to find the Zagar Mosaic, an incredible, block-long work of public art located along 5th Street near the Main Street Market. Created by noted Philadelphia artist Isaiah Zagar in 2000 as a gift from city philanthropist Gabe Silverman upon the grand opening of The Main Street Market, the mosaic features vibrant colors, abstract shapes, and a captivating design reminiscent of Picasso and Gaudi. The abstract shapes and colors are intended to represent “food, flowers, and markets.”


5. Visit an Art Museum 

UVA boasts two exquisite, and intimate, art museums, The Fralin and The Kluge-Ruhe Art Museum. The Fralin Art Museum is housed in a beautifully restored historic building overlooking the hallowed Mad Bowl on Rugby Avenue. Its 14,000-piece collection includes European and American painting, photography, works on paper, African art, and American Indian art and hosts several special exhibitions annually. The Kluge-Ruhe Art Museum is located inside a manor house on Pantops and contains the oldest and largest public collection of Aboriginal Australian art in the world. Here, visitors can explore the rich and vibrant art of Australia’s Indigenous peoples. The museum also features a variety of special exhibitions, educational programs, and events throughout the year. 


6. Play Pickleball!

Pickleball is Charlottesville’s newest game of choice, and on any given day you can hear the tell-tale, puck-puck of a fever-pitched match. Beginners and experienced players alike can find games at several public facilities located across town or, for a modest fee, visitors can play as guests at Boar’s Head Sports Club, The Greencroft Club, or ACAC. 


7. Take a Food Tour by Charlottesville Guide!

Food Tours by Charlottesville Guide is a great way to explore our vibrant food scene. With tours on the UVA Corner and the Downtown Mall, guests have the opportunity to explore two very different scenes. The UVA Corner Tour visits five restaurants from Bodo’s to Thyme & Company and invites guests to “dine like a student.” The Downtown Mall Tour is more “haute cuisine” and samples some of the Mall’s top restaurants, including The Bebedero, Hamiltons’, and Tonic. Both tours tell the colorful stories of the people and cuisine of each restaurant, as well as the cultural flavor of the neighborhood. Led by knowledgeable local guides, tours can last up to three hours. The UVA Corner Tour is $75 and the Downtown Mall is $99 per person. Reservations can be made at www.foodtoursbycharlottesvilleguide.com.


8. Visit the MEL  

The Memorial for Enslaved Laborers (MEL) was created by community collaboration and commemorates the lives of the enslaved laborers who built the University of Virginia. This memorial is situated on the University’s Grounds directly across from The Corner. Its elegant design is full of symbolism, inviting contemplation and reflection of the work done over 200 years ago. The memorial’s metal cylinder contains 4,000 marks to represent the number of enslaved laborers involved in building UVA. Its presence, at once beautiful and haunting, serves as an important reminder of the history and legacy of slavery in the region, and provides a valuable opportunity to reflect on this painful part of our city’s and nation’s history.


9. Visit The Lewis & Clark Exploratory Center

The idea of transcontinental exploration that became The Lewis & Clark Expedition was conceived right here in the early 1800s. Below Monticello and along the Rivanna River just downstream from land that was once the Clark Family Homestead, The Lewis & Clark Exploratory Center in Darden Towe Park is a must visit for both children and adults interested in the Corps of Discovery. The center sits on the site of the expedition’s final camp in 1806 and hosts a full-scale replica of the 1803 keelboat and a wide range of multimedia displays, videos, and artifacts that help you imagine what the rugged journey must have been like. 


10. Golf at Birdwood, Stoney Creek, and Old Trail

The terrain of the Virginia Piedmont is ideal for challenging golf along undulating fairways with mountain views. Here are three exceptional destinations to play the old game while traveling through Charlottesville:

1. Birdwood – Home of the UVA Cavaliers and redesigned by Tarheel Davis Love in 2020, Birdwood is a 7,116-yard, par 71 championship golf course just west of town. Greens fees begin at $85 for 9-holes up to $165 for 18 with a cart in season. www.boarsheadresort.com

2. Stoney Creek A Reese Jones design that opened in the late `80s, Stoney Creek is 20 minutes down Hwy. 151 in Nelson County with 27 holes averaging 7,100 yards at par 72. Characterized by its rolling terrain, elevation changes, and well-bunkered and undulating greens, Stoney Creek puts golfers in the middle of wine country. In-season greens fees are $109 on weekends including cart and range balls.

3. Old Trail – An 18-hole, 6,667-yard, par 72 links-style course designed by Jerry Kamis, Old Trail features rolling hills, lush Zoysia grass fairways, bent grass greens, and breathtaking views of the surrounding Blue Ridge Mountains. Greens fees range from $84 weekday to $104 weekend including cart, and tee times can be reserved up to seven days in advance. https://oldtrailclub.com


11. Stargaze at the McCormick Observatory

In 1885 Leander McCormick, whose family created the International Harvester Company, donated perhaps the world’s most powerful telescope to UVA. The observatory named for him sits at the summit of Mount Jefferson, aka Observatory Hill, and is one of the oldest observatories in the United States and has been in continuous use since it was built. Today, the observatory is still used for research and teaching and houses a museum dedicated to the history of astronomy and telescope design. The second floor is the observation deck, where visitors can view the night sky through the observatory’s historic telescope. The observatory is open and free to the public on the 1st and 3rd Fridays of every month if you make an advance reservation HERE


12.Compose at The Wall of Free Speech

At the east end of the Downtown Mall awaits a very public experiment that trembles at the core of our collective psyche – The Wall of Free Expression. Erected in the late `90s just as the truth of Sally Hemings DNA was surfacing, the Wall is a 54’ long chalkboard in the form of a monument to one of Thomas Jefferson’s most cherished ideas: Free Expression. Or is that scree expression? Loosely maintained by a local arts organization, an invisible force-field of tension surrounds the wall in both a testament to the banality of unregulated expression and the possibility of free-form inspiration. It’s hard to find this kind of tolerance anywhere else!


13. Do a Bodo’s Statue Walk

Embark on a quintessential Charlottesville experience by bagging a Deli-egg Bagel on Everything from the Corner Bodo’s and strolling across University Avenue to the UVA Grounds. Enjoy your Bodo’s on the Rotunda steps overlooking the Lawn, then set out to find these three statues.


Seated Thomas Jefferson among the Box – created by Viennese sculptor Karl Bitter and erected in 1915, this likeness of Jefferson is the final in a series of three statues by Bitter. The first, located in Cleveland, OH, depicts a young TJ, while the second,  “middle-aged” Jefferson, resides in Missouri. This final Jefferson shows the founder of UVA “in retirement,” and is partially hidden by large American boxwoods. 


Blind Homer with a Student Guide – created by Virginia native Moses Ezekiel in 1907, this was the first statue ever placed on The Lawn and symbolizes a Jeffersonian belief in educational hierarchy, where blind ancient poet Homer studies alongside a youthful student. The statue was originally commissioned for Amherst College in Massachusetts but in a cloudy history was redirected to UVA by an enthusiastic alumnus.


The Aviator – created by Gotzun Borglum, who is perhaps most famous for the presidential facades at Mount Rushmore, this statue was erected in 1917 and commemorates the first UVA student to die in WWI. The 12-and-a-half-foot statue depicts an athletic male in sandals and a helmet, or bone dome, as he launches into a modern Myth of Icarus.