The Perfect Charlottesville Virginia Itinerary 

Whether you are visiting Charlottesville for the day, a long weekend, your honeymoon or looking to relocate, there is so much to do here. 

Charlottesville is nestled in the foothills of the Blue Ridge Mountains about two and a half hours south of Washington, D.C. It’s home to the University of Virginia and is the gateway to Shenandoah National Park, Thomas Jefferson’s Monticello (a World Heritage Site), craft breweries and wineries, a huge outdoor music scene, dozens of local restaurants, and a beautiful walking mall. 

Whether you like hiking, wine, food, culture or college sports, there is something for everyone. 

When to Visit Charlottesville

Charlottesville is beautiful year ‘round, but it really shows off in the spring and fall. 

In the spring, temperatures are mild, cherry blossoms and dogwood blooms come out, azaleas are colorful, tulips are everywhere, and the outdoor farmers market really takes off. You can go strawberry picking or enjoy an outdoor meal on the downtown mall. There are also several great festivals worth attending, like the Tom Tom Founders Festival and Virginia Festival of the Book. 

In the fall, temperatures start to become crisp (a welcome relief after the hot-humid summer days). Everywhere trees begin to turn to orange, gold and red. You can enjoy a free outdoor concert at Sprint Pavilion downtown or a hot apple cider on Carter’s Mountain. Local farms host corn mazes and pumpkin patches and the whole town pauses for big football games. It’s basically a fall paradise! 

What to Do in Charlottesville

This guide will walk you through some of the best things to do in Charlottesville. I’ll also include suggested itineraries for both long weekends and a five-day stay in the area. 

Downtown Mall

The downtown mall in Charlottesville is one of the longest pedestrian malls in the United States. It spans eight blocks and includes restaurants, bookstores, clothing boutiques, theaters and even a children’s museum. 

Children’s Museum

Let’s start with the youngest visitors. The Virginia Discovery Museum caters to preschool- and elementary-aged children. It’s one of the smaller children’s museums in Virginia and probably wouldn’t hold the attention of older children for more than an hour or two. But if you are in the area with preschoolers, it’s well worth a visit, especially if it’s rainy and you could use an indoor venue.

Fridays After Five and the Ting Pavilion

Fridays After Five is a series of free outdoor concerts held every Friday from the middle of April through the middle of September. They happen at the Ting Pavilion, which is located at the end of the downtown mall (right beside the Children’s Museum). People come, set up picnic blankets, let their kids run around, and dance. Or they visit the pavilion before or after enjoying dinner in nearby restaurants.

Live Music at Vineyards

Throughout the summer months many of the local vineyards and breweries also host free outdoor concerts and food trucks. Usually the concerts happen in the late afternoon or early evening. People bring picnics, their kids, blankets and chairs and spend time sipping craft brews or other drinks. You can find out about these events by checking Facebook or Google events or by following specific vineyards or breweries. Keswick Vineyards, Eastwood Farm and Winery, Pippin Hill, Valley Road, Blue Mountain Brewery, Pro Re Nata, Chisholm Vineyards at Adventure Farm, Hark Vineyard and Glass House Winery all frequently host these types of events. 

Rivanna Roots

Continuing on the live music theme, in 2022 three local groups are starting a new family-friendly outdoor music series called Rivanna Roots. The series will include 11 concerts scheduled on alternating Thursdays and Saturdays starting May 21st. The concerts will take place on the property of the Rivanna River Company and are fundraisers for the Front Porch – a local music school. 

Rivanna River Company

Before you go to a Rivanna Roots concert you may want to spend the day on the Rivanna River. The Rivanna River Company hosts both guided trips and do-it-yourself rentals. You can rent canoes, kayaks, tubes or stand-up paddle boards. Or you can book a guided river trip. Some rentals include shuttle service while others are completely self-propelled. 

Skyline Drive

Skyline Drive is the 105-mile road that runs along the mountain ridges of Shenandoah National Park. Many people choose to take this route on pretty days, enjoying the scenery at a slow pace (the speed limit is mostly 35 MPH), and pulling off at one of the 75 overlooks for panoramic views or a picnic. Skyline Drive is only a 25-minute drive from downtown Charlottesville.

Blue Ridge Parkway

The north entrance of the Blue Ridge Parkway starts at the south entrance of Skyline Drive. In other words, Skyline Drive takes you northward through Shenandoah, and the Blue Ridge Parkway takes you southward toward Roanoke, but they are basically the same road. 

Five miles down the Blue Ridge Parkway you’ll get to the parking area for Humpback Rock. Hiking Humpback Rock to see the sunrise is almost a rite of passage for UVA students. The steep .7 mile hike leads to 365-degree views of the Shenandoah Valley and Blue Ridge Mountains. Leave 45 minutes for the hike up – there are benches along the way if you need a break along and along. 

If you continue a little farther down the Blue Ridge Parkway you’ll get to Raven’s Roost. Raven’s Roost is probably the most popular sunset watching spot in the area. The views are spectacular but expect crowds and photographers 7 days a week. 

For a less crowded hike/walk on the Blue Ridge Parkway, consider Cedar Cliffs – a lovely .7 mile moderate jaunt to beautiful west-facing views. 

Saunders-Monticello Trail 

If you want a beautiful trail without leaving Charlottesville then the Saunders-Monticello Trail might be right for you. Parking can be tough as it’s a popular local dog-walking/running/biking trail, so get there early if possible. (There are two parking areas so if the first one is full, continue on the road to find the second one.) The trail takes you two miles up Carter’s Mountain to Monticello. It’s considered wheelchair accessible and is dog friendly until you reach the boardwalk (at which point dog walkers must turn around). 

Carter’s Mountain 

At the top of Carter’s Mountain is an orchard by the same name. Carter’s Mountain is particularly popular in the fall as a place to buy apple cider donuts, pick apples and drink cider. There is often live music on the weekends and food trucks. Bold Rock Cider is located in the bottom of the country store and patrons enjoy a flight or pint on beautiful days. 

Monticello

Right beside Carter’s Mountain is Thomas Jefferson’s Monticello. Jefferson was the third president of the United States, principal author of the Declaration of Independence and founder of the University of Virginia. He also had more than 600 enslaved people working under him. Monticello is his estate. You may recognize it from one side of the U.S. nickel. The estate showcases his eclectic interests and intellect, and it also, in more recent years, acknowledges and highlights the suffering and contributions of those in bondage. Monticello is the only World Heritage Site in Virginia. 

James Monroe’s Highlands

Down the road from Monticello is the estate of James Monroe – the fifth president of the United States. Highland offers both private and guided tours of the estate. There is also a trail system that can be used free of charge. If there’s been recent rainfall, be aware that the trails have a tendency to be muddy. Highland also hosts events and is a popular wedding venue. 

Montpelier 

For even more early American history, head 25 miles northeast of Charlottesville to Montpelier. Montpelier is the estate of James Madison (fourth president of the United States.) You can take a guided tour of James’ and Dolly’s house at Montpelier. But my favorite activity is to park by the gift shop and explore the  eight-plus miles of walking trails on the 2,650-acre property. 

Market at Grelen

After you visit Montpelier, head over to the Market at Grelen for lunch, fresh ice cream and a pick-your-own farm. During spring and summer months you can pick berries, peaches, apples and plums. In the winter they sell Christmas trees and wreaths. And year around you can buy plants from their nursery and greenhouse. My husband enjoys getting a local beer there, I like the fresh-made ice cream often flavored with in-season fruit, and my toddler heads to the sandbox.

Liberty Mills

After you have lunch at the Market at Grelen head over to Liberty Mills. If it’s fall you can enjoy the country’s largest corn maze, tractor rides and a pumpkin patch. In the spring they have pick your own strawberries and in the summer you can pick your own flowers. It’s a popular local outing for families. 

Hot Air Ballooning 

If adventure is more your style or you’re looking for something totally adult to do, you might try booking a hot air balloon ride. Hot air balloon rides occur mostly in the warmer months and are scheduled around sunrise or sunset. They require specific conditions (if it’s too windy or it might rain, then they can’t fly), but are an incredible way to get a bird’s eye view of the Blue Ridge Mountains and Piedmont. 

University of Virginia

The University of Virginia was founded by Thomas Jefferson and the buildings and grounds reflect its history. Take a stroll through the main rotunda and central grounds. Attend a sports match or take in a play. UVA also often hosts speakers and forums that are open to the general public. You can find up-to-date information here.

Farmer’s Market

Charlottesville has two main open-air markets. And they are pretty close to one another. The Charlottesville City Market is located by the downtown mall. It is held on Saturday mornings from May to November. 

The Farmer’s Market at IX Art Park happens year round on Saturday mornings. It’s also held Thursday evenings in the summer months. 

IX Art Park

The IX Art Park is a quirky indoor-outdoor art space that features big sculptures, children’s art classes, a makerspace, and the locally-owned American Sake Brewery and Three Notch’d Brewery restaurant-bar.​​ It is also the site of The Looking Glass, an immersive art experience, filled with light and whimsy, which takes about an hour to walk through (entrance fee charged for those over the age of 3). The outdoor space is also used for concerts, social dances, a seasonal farmers market, and community-centered activities like the Black Business Expo, Cville Sabroso Latin American food and culture festival, and Hip-Hop Cultural Fest. 

Theater and Live Music

Charlottesville is a hub for live music and local theater. The Jefferson Theater, Ting Pavilion, Paramount Theater and John Paul Jones Arena all host live music events ranging from local artists to big name events. 

Vineyard Tour

This region has more than 40 wineries. So if you love wine it’s a really good place to be! Several companies offer private tours, which is definitely the way to go if you want to really enjoy yourself and not worry about having a designated driver! 

Here are a few to check out: Blue Ridge Wine Excursions, Monticello Wine Tour and Coach Co., Central Virginia Wine Tours. 

Horseback Riding 

If you want to add fresh air in a saddle to your wine tour, book a horseback riding tour! There are several companies that offer this experience, but essentially they’ll take you through a vineyard (or brewery) on horseback and then you have a wine tasting at the vineyard (or beer tasting at the brewery). Tours are offered at Keswick, King Family, Veritas, Blue Quartz Winery, Devil’s Backbone Brewery and Castle Hill Cider, but they should be booked through one of the tour companies. 

Blue Ridge Tunnel

The Blue Ridge Tunnel is a historic railroad tunnel built during the 1850s. It recently opened as a walking and cycling trail. End to end it’s 2.25 miles long. It’s flat, so it’s stroller and wheelchair friendly but it lacks lights, so make sure you bring flashlights or headlamps. The tunnel is located at the convergence of the southern entrance of Shenandoah National Park’s Skyline Drive, the northern entrance of the Blue Ridge Parkway, the Appalachian Trail, and U. S. Bicycle Route 76. Both Interstate 64 and U. S. 250 cross over the tunnel at Rockfish Gap.

Brew Ridge Trail

The Brew Ridge Trail is a self-guided tour of Virginia’s craft beer and cideries. It starts with Blue Mountain Brewery in Afton and goes south to the Blue Mountain Barrel House (owned by the same company). Eleven stops are recommended in between. 

Bar Crawl Scavenger Hunt 

If you want to take in the local bars without leaving Charlottesville but are looking for something different to do, then try the Bar Crawl Scavenger Hunt! Put together by the company Let’s Roam, the scavenger hunt is self guided and can be done at any time. The Bar Hunt is billed as “one part bar crawl, one part scavenger hunt.” As you bar hop you complete photo, video and trivia challenges with your team. 

Kluge-Ruhe Aboriginal Art Collection of the University of Virginia

The Kluge-Ruhe Aboriginal Art Collection is the only collection outside of Australia that is dedicated to Aboriginal Art. The collection features more than 2200 pieces and there are rotating exhibits. Visiting usually takes 20-30 minutes and free guided tours are available twice a day.

Resorts

If you’re looking for a luxury experience you might consider staying at the Boar’s Head or Keswick Hall. Both offer luxury suites and dining, golf courses and pools. The Boar’s Head also has a full spa experience available, a sports club and private trails. 

Rock Climbing Gym

If you’re ready to work off some of the beer and wine you’ve been enjoying, you might consider hitting up Rocky Top – Charlottesville’s bouldering gym. Bouldering is a type of climbing that does not require ropes. Whether you are an experienced climber or just looking for something fun to do (with or without kids), check it out and get some exercise while you’re at it!

Biking Tour

Virginia has some of the most beautiful road biking terrain on the east coast. And if that’s your thing, or you want it to be your thing, Blue Ridge Cycling Tour can show you Charlottesville by two wheels. They offer everything from winery tours to multi-day road trips to easy around-town jaunts. 

Historial Tour

The Albemarle Charlottesville Historical Society offers year-round guided walking tours of some of Charlottesville’s historic monuments and buildings. Two current offerings include a tour of Court Square, which covers pre-revolutionary to recent history and a tour of Maplewood cemetery: Charlottesville’s oldest public cemetery. 

Taste of Charlottesville Food Tour 

The Taste of Charlottesville Food Tour combines food tasting with a historical tour of downtown Charlottesville. The walking tour includes seven samples at six stops and takes approximately three hours to complete. 

Cooking Class

Have you ever wanted to learn how to make ravioli from scratch? Or roll the perfect sushi? Or always wanted to know how to make dumplings? Then try a cooking class! Charlottesville has two companies who offer cooking classes – the Happy Cook (which is also a cooking store) and Culinary Concepts. 

Swimming Holes and Lakes

In the summer, try cooling off at one of the local swimming holes! The most popular one is Blue Hole at Sugar Hollow in Crozet. It’s a beautiful spot and a short hike to the swimming hole, but it can get very crowded on the weekends. I recommend making it a mid-week jaunt and avoiding it on Saturday and Sunday. 

Chris Greene Lake, Mint Valley Springs Park and Walnut Creek all have dedicated swimming areas with beaches. 

In Shenandoah National Park, White Oak Canyon and Rip Rap Hollow hikes both feature swimming holes. Both are considered challenging and/or longer hikes. 

Where to Stay in Charlottesville 

If camping is your thing there are tons of options in Charlottesville. Shenandoah National Park has five campgrounds. Misty Mountain is a privately owned campground that features a playground for kids, pool and volleyball courts. If you’re looking for something a little more secluded, you can stay on private property through the agencies HipCamp and Tentrr.

Airbnb and VRBO both have a strong presence in Charlottesville. You can book anything from private rooms to yurts to cabins to manors and estates through those platforms. 

If you love Bed and Breakfasts check out: 

• 200 South Street Inn
• The Dinsmore House
• Oakhurst Inn
• The Inn at Court Square

If boutique hotels are your thing I recommend: 

• The Quirk Hotel 
• The Clifton 
• The Draftsman

For proximity to the downtown pedestrian mall, The Omni Charlottesville Hotel can’t be beat. It anchors one end of the mall.

Where to Eat in Charlottesville

Charlottesville has an amazing local food scene.This list is by no means exhaustive, but it will give you a good place to start. Almost all of the restaurants in Charlottesville offer vegetarian options, but I’ll put a “V” by the ones I consider especially vegetarian friendly. 

If you’re only visiting for a day or two, here is my shortlist of top ten best local restaurants in Charlottesville. These are every day eateries – for fine dining, scroll down. 

• Bodos Bagels
• Feast!
• Pineapples Thai
• Kanak Indian Kitchen
• Pearl Island
• Otto Turkish Street Food
• Guajiros Miami Eatery 
• Tacos Gomez 
• Vu Noodles
• Jack Brown’s 

Breakfast

Some of these places serve lunch all the time while others have weekend brunch menus. We love Bodos Bagels for quick breakfast sandwiches, Ace has the best biscuits in town, MarieBette for pastries, and Tip Top for diner-country-style breakfast. 

• Tip Top 
• Moose’s by the Creek
• Bodos Bagels
• Farm Bell Kitchen
• Ace Biscuit and Barbeque 
• MarieBette Cafe and Bakery 
• Crosby’s Urban Vittals 
• Blue Moon Diner
• Villa Diner
• Peloton Station

Lunch 

Most of the restaurants in Charlottesville that serve dinner also serve lunch, but here are a few that serve what I would call “lighter lunch.” Meaning they focus on salads and soup and sandwiches and do it really, really well.

• Tilman’s 
• Roots (v)
• Revolutionary Soup (v)
• Riverside Lunch
• Kitchenette Sandwich Shop
• Baggby’s Gourmet Sandwiches 
• Mel’s Cafe
• Feast! (v)
• Mezeh (v)
• The Juice Laundry (v)

Dinner

• Afghan Kabob Palace

• Al Carbon
• Bang! (v)
• The Bebedero 
• Brazos Tacos (v)
• C&O Restaurant
• Cafe Frank
• Citizen’s Burger Bar
• Doma Korean Kitchen (v)
• Duner’s Restaurant 
• Firefly (v)
• Fleurie 
• Iron Paffles and Coffee
• Kardinal Hall (v)
• Mahana Fresh
• Marco and Luca’s Noodle Shop
• Maru Korean Restaurant 
• Milan Indian (v)
• Kanak Indian (v)
• Otto Turkish Street Food (v)
• Botanical  (v)
• Pad Thai (v)
• Pearl Island (v)
• Soul Food Joint
• Sultan Kebab
• Vu Noodles (v)

Dessert

• Albemarle Baking Co.
• Cake Bloom
• MarieBette Cafe
• Kilwins 
• The Pie Chest
• Bowerbird Bakeshop

Coffeeshops

• Quirk Cafe
• Shenandoah Joe
• Grit
• Lone Light Coffeehouse 
• C’ville Coffee

Charlottesville Two-Day Itinerary 

Grab a cup of coffee at Lone Light Coffee and a pastry from Mariebette. Then, if it’s a Saturday in the summer, hit up the Farmer’s Market at IX Art Park. Get some snacks from the vendors and windowshop local art. Visit The Looking Glass Art exhibit. Grab lunch to go from Vu Noodles or Otto Turkish Street Food. By 1 pm meet up with your wine tour guide. Spend the afternoon exploring several different local wineries.

Have a late dinner at Kanak Indian Kitchen and an early night in.

Get up before dawn and head to the Blue Ridge Parkway for a sunrise hike at Humpback Rock. Watch the sun come up over the Blue Ridge Mountains. On your way back into town grab breakfast from Bodo’s Bagels. Shower and take a breather before heading back out.

Spend early afternoon meandering down the downtown pedestrian mall. Grab lunch somewhere that strikes your fancy, probably one with outdoor seating. Then go to Monticello and take a tour (they close at 5 so get there by 3!) Grab a slice of pizza from Lampo and then meet your hot air balloon tour guide. Watch the sunset from the sky. End the day with tapas and drinks from Bang!

Charlottesville Five Day Itinerary

Day 1: Downtown

On your first day in town I suggest focusing on the city center itself. Walk the downtown pedestrian mall, take in The Looking Glass exhibit, meander through local bookstores and boutiques, catch a show at the Sprint Pavilion or live music at one of the local bars. Get ice cream at Kilwins, burgers at Jack Brown’s and sip drinks on the rooftop of the Quirk. 

Day 2: U.S. History 

Grab a bagel from Bodos and then head up to Monticello to get there when it opens. Take a tour and stroll the grounds. Grab lunch at the historical Michie Tavern. Stroll along the Saunders Monticello Trail in Kemper Park. Then head up to Carter’s Mountain for a glass of Bold Rock Cider and a mid-after apple cider donut. Head out for a hot air balloon ride with Monticello Balloon Company. Have dinner and drinks at Kanak Indian Kitchen or Soul Food. 

Day 3: Shenandoah National Park

Pack a picnic and lots of snacks and head to Shenandoah National Park. Spend the day driving down Skyline Drive. Tackle some short hikes – a few favorites are Little Calf Mountain, Blackrock Summit, Doyles River Falls and Hightop Mountain. Watch the sunset from an overlook. Drink some local beer that you brought with you. Grab dinner back in town at The Bebedero.

Day 4: Vineyard Tour

Have a leisurely breakfast amid locals at Tip Top followed by a walk on the Rivanna Trail. Grab lunch from Riverside Diner then meet up with your vineyard tour guide. Spend the next five hours exploring some of Charlottesville’s best vineyards. After your tour, head downtown and listen to some music at Fridays After Five. Grab dinner on the downtown mall. 

Day 5: Last Day 

Start your day at the Farmer’s Market or at Albemarle Baking Company. Get some snacks and treats and then head over to the Rivanna River Company to pick up tubes. Spend two hours lazily floating down the river. Grab lunch from Tacos Gomez. Clean up and then head out for a Taste of Charlottesville walking food tour. End the night with some live music and local beer at Peloton Station. 

I hope this guide was helpful as you visit Charlottesville!