Charlottesville may be small, but it sure does pack a punch when it comes to fun things to do! It’s no secret that C’ville is a mecca for outdoor enthusiasts. Located in the foothills of the Blue Ridge Mountains and just 30 minutes from the 500 miles of trails in Shenandoah National Park, you’ll have ample opportunities to get outside. 

Surrounded by farms, orchards, and dairies, Charlottesville is a foodie-centric city that takes its farm-to-table game very seriously. You can spend your time sipping local wines on the Monticello Wine Trail or sampling local apple ciders at one of Charlottesville’s many cideries. From exploring the spectacular University of Virginia campus to hunting down historic attractions to taking a scenic drive to check out the fall foliage, there are countless reasons you’re going to fall head over heels for Charlottesville! 

With so many things to see, do, and eat, you might not know where to begin. So we’ve compiled our list of the absolute best things to do in Charlottesville for you. Stick to these fun and unique Charlottesville bucket list recommendations, and there’s no doubt you’ll have an amazing time in this truly unique Virginia city!

Don’t forget to check out our web story: The 15 Best Things to Do in Charlottesville, VA

The 15 Best Things to Do in Charlottesville 

1. Follow the Monticello Wine Trail

Virginia is home to over 300 wineries. Luckily, some of the best of the bunch are located near Charlottesville on the Monticello Wine Trail! Whether you’re in town on a romantic vacation or a girl’s getaway, we highly recommend dedicating at least one day to sipping and swirling. 

You’ll find 30 wineries along the Monticello Wine Trail, all within a 25-minute drive from downtown Charlottesville. There’s no way you can visit them all in one day, so be sure to pick up your Monticello Wine Trail Passport. That way, you can keep track of your progress for your next visit to Charlottesville. 

For a little bit of history, don’t miss out on Jefferson Vineyards. You can sip a glass of their award-winning Viognier on the very spot Thomas Jefferson chose to grow grapes nearly 250 years ago. 

For something a bit more chill, head over to Dave Matthews’ very own Blenheim Vineyards. Instagram addicts will love sipping wines and snapping selfies at the beautiful Veritas Vineyard and Winery, while wine aficionados will want to take a fascinating tour of King Family Vineyards.

Whichever wineries you choose, expect to come across all sorts of pop-up events, live musical performances, and locally-sourced cheese boards along the way! 

2. Tour the University of Virginia Campus 

You probably didn’t know this, but the University of Virginia is the first American university to be registered as a UNESCO World Heritage Site! Thomas Jefferson actually founded the University of Virginia in 1819 as part of his commitment to education. 

Fast-forward to today, and the university is still famous for its impeccable grounds and stunning Neoclassical architecture. If you’ve got the time, it’s well worth taking one of the free, student-led tours to take it all in. 

The daily tours start at the iconic Rotunda, which dates back to 1826. Along the way, you’ll come across beautiful gardens, an expansive grassy courtyard called the Lawn, 10 pavilions, and a variety of historic structures.

If you have time, stop off at The Raven Room, which was the dorm room of author Edgar Allen Poe. You’ll find all sorts of tributes to the writer, including a stuffed raven and pieces of furniture from his own home. Or, if you’d prefer to check out some art, head over to the Fralin Museum of Art or the Kluge-Ruhe Aboriginal Art Collection of UVA. 

3. Take a Scenic Drive in Shenandoah National Park

Taking a day trip to Shenandoah National Park should be at the top of any nature lover’s Charlottesville bucket list. With 500 miles of hiking trails, cascading waterfalls, towering peaks, and stunning lookout points, it’s impossible not to be enamored with this beautiful national park.

But if you’ve only got time for one activity, take a mini road trip along Skyline Drive. You’ll want to allot a full day to tackle the 105-mile-long stretch of road. While the drive itself will take about three hours, you’ll want to leave plenty of time to hike at least a few trails and take as many photos as possible!

For some of the best views on Skyline Drive, you’ll want to stop off at The Range View Overlook and The Point Overlook. That being said, you’ll pass dozens upon dozens of viewpoints along the way. Time your visit with the first week of October, and you’ll be rewarded with spectacular views of the fall foliage.

4. Eat at Dairy Market 

If you consider yourself a foodie or just love to eat, visiting Dairy Market is one of the most fun things to do in Charlottesville. Housed in the 1936 Monticello Dairy building, Dairy Market opened its doors in 2020 and quickly became one of the coolest Charlottesville attractions. 

Dairy Market prides itself on being the first market hall in Central Virginia. Today, the space is home to roughly 18 unique vendors, all dishing out seriously good eats and seriously cool products. 

Head over to Angelic’s for their signature Southern-style fish and comforting soul food dishes. There’s also Thai street food at Chimm St., delectable wood-fired pizza at Dino’s, authentic Filipino food at Manila Street, and so much more. If you need something to wash your meal down with, grab a curated cocktail at The Milkman’s Bar or a local craft brew at Starr Hill Brewing. 

It’s not all about the food, though. You can also shop for clothes, home goods, and more! Plus, there are always pop-up events and live music going on at Dairy Market. Be sure to check their website to see what’s going on during your visit. 

5. Learn about Slavery at Thomas Jefferson’s Monticello

Thomas Jefferson built his Monticello farm, plantation, and estate in 1772, and it was the primary plantation and residence of the third President until his death in 1826.

It is now a designated National Historic Landmark and UNESCO World Heritage Site, famous for its neoclassical architecture, sprawling grounds, and impressive collection of Jefferson’s personal items and artifacts. But one of the most interesting, important, and sobering things about visiting Monticello is learning about its slave history.

It’s possible to take a variety of tours that detail the realities of what life was like for the 400 slaves who lived and worked at Monticello. The Hemings Family Tour focuses on the Hemings family, one of the best-documented enslaved families in the US. You’ll also learn all about the story of Sally Hemings, who was the mother of six of Jefferson’s children. 

6. Have a Beach Day at Walnut Creek Park

When you think of Charlottesville, having a beach day is probably the last thing that comes to mind. But that’s where Walnut Creek Park comes into play!

Located an easy 25-minute drive from downtown Charlottesville this tree-studded park sits on 525 acres of land, including 45 water acres and two beach acres. The beach is open for swimming from 11 am to 7 pm from Memorial Day to Labor Day. 

The sandy beaches are a prime spot to soak up the summer sun. You can easily spend an entire day here, so be sure to pack a picnic lunch. There are also plenty of grills and picnic tables in the park if you feel like having a barbecue. 

If you’re looking for more action, you’ll find 15 miles of scenic hiking and biking trails in Walnut Creek Park. There’s also an 18-hole disc golf course as well as plenty of opportunities for boating, kayaking, and fishing.

7. Shop in the Historic Downtown Mall

A trip to the Historic Downtown Mall is definitely one of the most fun Charlottesville attractions. Located right in the heart of downtown, this pedestrian-only area takes up eight tree-lined blocks. It’s actually one of the longest pedestrian malls in the United States! 

One of the coolest things about Downtown Mall is that it’s made up of rows of historic buildings, which have been lovingly restored. But that’s not all. You’ll also find dozens of restaurants lining the streets, as well as over 100 shops and a handful of art galleries, live music venues, and historic theaters.

You can spend your mornings sipping locally roasted coffee at a quaint cafe, your afternoons shopping for goods made by Virginia-based artists and artisans, and your evenings dining in one of the area’s international restaurants.

Time your visit for a Friday evening, and you’ll have the chance to attend the Fridays After 5 concert series. Or, if you happen to be there on a Saturday morning, you’ll find over 100 vendors hawking locally sourced food and goods at the popular “City Market” farmers’ market (adjacent to Downtown Mall).

8. Pick Fruit at Carter Mountain Orchard

If you’re looking for family-friendly things to do in Charlottesville, spending an afternoon at Carter Mountain Orchard should be at the top of your to-do list! This is the place to go to pick your own fresh fruits and veggies straight from the orchard. Think apples, strawberries, peaches, and so much more (depending on the season, of course)!

There’s also the adorable Country Store & Bakery on-site, where you can shop for seasonal fruits and veggies, as well as an impressive selection of specialty foods. Plus, the bakery dishes out some seriously good apple cider donuts and other sweet treats everyone in the family is sure to love.

Carter Mountain Orchard is set high up on Carters Mountain Trail, so you’ll be treated to spectacular views of Charlottesville and the Blue Ridge Mountains. If you want to sample some local wine, you can even order a flight of Carter Mountain Wine from the on-site wine store, sit back and relax at an outdoor table, and enjoy the views.

9. Catch a Sunset from Humpback Rock

Taking a hike to Humpback Rocks is easily one of the top Charlottesville activities for outdoor enthusiasts. The popular trail is located in George Washington National Forest, which is a 30-minute drive from Charlottesville on the Blue Ridge Parkway.

You can choose from a variety of shorter and longer trail options. Whichever way you go, a hike to the summit of Humpback Rocks will reward you with stunning views from the top. For the most magical vistas, visit during sunset or sunrise and enjoy the show!

If you opt for the Humpback Rocks Trail, you’ll ascend 800 feet in one mile to reach Humpback Rocks via the moderate to difficult trail. This is where you’ll take in 360-degree views of Virginia’s Shenandoah Valley. For those lucky enough to do this hike in the fall, the views of the fall foliage are nothing short of spectacular.

You can either return the way you came or keep going for an additional mile to reach Humpback Mountain, or go even further to reach the Humpback Rocks picnic area (a total of 3.9 miles).  

10. Explore Luray Caverns

If you’re looking for unique things to do in Charlottesville, you’ll definitely want to add a visit to Luray Caverns to the list. This natural wonder dates back to 4 million years ago and is located 90 minutes from Charlottesville, so it does take a bit of effort to reach.

Luray Caverns is the largest series of caverns in the eastern United States. Take a tour of these mysterious caverns, and you’ll be led to rooms the size of cathedrals, with some boasting ceilings as tall as 10 stories. 

You’ll also come across dramatic clusters of stalactites and stalagmites, as well as shimmering draperies and incredible mirrored pools. Don’t miss out on the Great Stalacpipe Organ, which is spread out over 3.5 acres and is the world’s largest instrument, according to the Guinness World Records. The ancient stalactites are tapped using rubber mallets and produce a variety of different tones!

11. Dine at the Best Farm-to-Table Restaurants

Charlottesville is an unabashedly foodie city, so taking some time to sample some of its best eats is a must. One of the coolest things about C’ville’s restaurant scene is the importance placed on locally sourced ingredients and the overall support of small local businesses. 

Charlottesville is surrounded by an impressive number of farms, orchards, dairies, and vineyards, which means there’s no shortage of farm-fresh ingredients for local chefs to get creative with. You can start your culinary journey at The Local for upscale Appalachian dishes sourced (almost) entirely from local farms. Think Local “Buffalo Creek Beef” Short Ribs, “Caromont” Goat Cheese Salad, and Lobster Mac and “Mountain View” Cheese.

There’s also Orzo Kitchen & Wine Bar for farm-to-table Mediterranean dishes and Mas Tapas for creative Spanish-style tapas with a local twist. For casual meals, Boylan Heights dishes out massive burgers with beef and produce sourced from local farms. Or, for something a bit more refined, head over to C&O Restaurant for French country fare and an impressive list of Virginia wines.

Or, for a one-stop-shop for farm-to-table eats, head over to the Charlottesville City Market, where you can sample all sorts of creative bites.

12. Relax at Keswick Hall

If you’re in town to enjoy a relaxing retreat, a stay at the incredible Keswick Hall should be at the top of your Charlottesville bucket list. You’ll find this sprawling property just 7 miles outside of the city center. But with so many pampering amenities, you’ll probably find it almost impossible to tear yourself away! 

You can spend your entire trip taking in golf course views from the adults-only Horizon Pool, getting massages at the spa, teeing off on the 18-hole Pete Dye-designed golf course, or simply sipping poolside cocktails. 

Once you work up an appetite, you’ll be spoiled for choice with the dining options. Start with a handcrafted cocktail or two at Crawford’s Bar before indulging in farm-to-table Jean-Georges dishes at Marigold. Better yet, wrap yourself in your sumptuous robe, get comfy on your luxury bed, and enjoy gourmet Jean-Georges dishes from the comfort of your incredible hotel room!

13. Hike to Crabtree Falls

If you’re looking to get out in nature, hiking to Crabtree Falls is one of the coolest things to do in Charlottesville. Tucked away in the Blue Ridge Mountains, Crabtree Falls is made up of a series of waterfalls that cascade 1,200 feet down the rocky mountain surface. It just so happens to be the tallest cascade in the Eastern United States!

is roughly one hour from the heart of Charlottesville, but it’s well worth making the effort to reach it. From the parking lot, you’ll walk up the mountain, alongside the falls, using a combination of built-in stairs and well-trodden trails. 

The hike is strenuous and steep but not too challenging. You can either opt to do the 2.5-mile loop or the out-and-back trail, which can take roughly 2 hours.

As with any hike near Charlottesville, the best time to lace up your hiking boots is in the fall, when you’ll have a chance to check out the beautiful fall foliage. It makes the scene even more magical!

14. Go Cidery Hopping

Thanks to all of the local, fruit-filled orchards, cider is a huge deal in Virginia. But C’ville takes things up a notch and is proudly home to the most cideries in the state. 

This cider culture goes way back. Early settlers of the New World were quick to plant apple trees to make cider in order to make up for the lack of barley and hops. George Washington, John Adams, and Thomas Jefferson were all huge apple cider fans! 

Today, you’ll find at least eight cideries within an hour of downtown Charlottesville. So if you’re looking for unique Charlottesville attractions, cidery hopping is always a good idea! 

You can start off with award-winning craft ciders at Bold Rock, where you can also pick fruit from the orchard and enjoy their famous apple cider donuts. Then head over to Castle Hill Cider for their delicious artisanal ciders or Blue Toad Hard Cider, where you can sip and snack on delicious eats at one of the many visiting food trucks. 

Then there’s Albemarle Ciderworks, which grows more than 200 apple varieties in their orchard, and Bryant’s Cider, which is all about creating unique flavors using unlikely ingredients like habaneros and rosemary.

15. Find the Best Food Trucks

It’s no secret that Charlottesville is a foodie city and that locals take their farm-to-table cuisine very seriously. But if you’re looking for dining options that are a bit more funky and unique, you’ll love that C’ville has a huge food truck scene. 

Hunting down some of the city’s best and most popular food trucks is an amazing way to get a taste for the diverse and innovative culinary culture – you just have to find them first! When you do, you’ll understand just how globally -inspired Charlottesville’s chefs are.

You’ll find beef empanadas and mixed ceviche at Pachamama Peru, meat- and veggie-topped wood-fired pizzas at Bella Luna, and Salvadoran pupusas and traditional appetizers at Gloria’s Pupuseria. 

From ramen food trucks to kettle corn food trucks, you’ll find all sorts of creative bites around town. The best way to find out the times and locations of individual trucks is by following their social media pages. Or, there will usually be a bunch hanging around the C’ville farmers’ markets.

There you have it! The 15 best things to do in Charlottesville. What’s your favorite thing to do in Charlottesville?

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