7 Days in Virginia: Road Trip Itinerary with Packing Suggestions

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You could spend weeks traveling in Virginia, but for the visitor who wants an introduction to the entire state, below is a seven-day road trip itinerary starting and ending in Richmond, the capital and closest city to the airport. 

This itinerary hits some of the most famous tourist attractions, but leaves out many. This is partly to give you a few off-the-beaten-path experiences and partly to cover as much geographic area as possible within a week.

Following this itinerary, you will visit Richmond, Colonial Williamsburg, Charlottesville, Farmville, Abingdon, and Grayson Highlands State Park. This itinerary will not take you to the beaches or the American Shakespeare Center.

This itinerary is designed to give you a focus each day while also allowing you time to walk through neighborhoods, explore attractions you learned about along the way, and in general, not have every minute planned out. 

Virginia Road Trip Itinerary Breakdown

• Day 1: Richmond
  • Trolley Tour
  • Self-Guided Street Art Walking Tour
  • VA Museum of Fine Arts
• Day 2: Colonial Williamsburg
• Day 3: Charlottesville
• Day 4: Farmville
  • High Bridge Trail State Park
  • R. R. Moton Museum
• Day 5: Abingdon
• Day 6: Grayson Highlands State Park
• Day 7: Richmond
  • Valentine Museum
  • Edgar Allan Poe Museum
  • Riverfront Canal Cruise
  • Riverfront Canal Walk

Day 1: Richmond

About Richmond

Richmond is the capital city of Virginia and offers many museums, restaurants, festivals, and outdoor activities.  You could easily spend a whole week exploring the greater Richmond area, but this itinerary will give you a taste of what’s available. The listed activities were selected from those available year-round.

As a side note, Richmond, Virginia is locally often abbreviated to RVA. You’ll see this abbreviation used in many festival titles and other local advertising.

Packing Suggestions

• Jeans or trousers (hiking pants are fine)
• Plain top (long sleeves for winter)
• Jacket or cardigan (for air-conditioned buildings or as a mid-layer in winter)
• Comfortable walking shoes (sandals are good for summer)
• Warm coat, gloves, and hat (winter) – Here are some cold weather packing tips to help.

You’ll see students dressed in pajama pants, politicians in suits, and everything in between, so dressing in nicer casual clothes should serve you for all the places in this travel plan. Also note that it is rare to see people in non-Western clothing in Richmond, so be prepared for stares and questions if you dress in non-Western clothes. 

The summers are very humid, so quick-dry, breathable clothing is most comfortable. You may want to pack a rain jacket. The James River runs through Richmond and the city often gets rain, but few people use an umbrella. Most people get wet or wear a rain jacket.

Your Day in Detail

Be prepared to pay for parking in downtown Richmond. There are websites to help you plan where to park and how much it will cost.

Today, you’ll be taking a trolley tour (be sure to buy tickets in advance) to get a feel for the layout of downtown.

After the trolley tour, go on a self-guided walking tour and see some of Richmond’s murals and other street art. Depending on when you’re in Richmond, you might even get to visit the RVA Street Art Festival and watch artists at work.

For lunch, head to the VA Museum of Fine Arts. This museum has a restaurant and a cafe. There is a paid parking garage on site that typically has ample availability.

Plan to spend all afternoon at this museum. Even the free exhibits can take hours to walk through. Besides paintings, there are objects from African countries, jewelry from the United States, and more. The free, permanent exhibits mostly feature art from Europe and the United States, but the paid, temporary exhibits come from around the world.

After leaving the museum, find street parking near a restaurant for supper or head out of downtown for restaurant options that are more likely to have free, onsite parking.

Day 2: Colonial Williamsburg, Charlottesville, and Travel Day

About Colonial Williamsburg and Charlottesville

Colonial Williamsburg is an entire village dedicated to colonial history. You will need to purchase tickets for building tours. There is plenty of free parking at the Visitor Center. From there, you can take a complimentary shuttle to the historic district.

Charlottesville is the home of the University of Virginia, founded by Thomas Jefferson in 1819. Downtown Charlottesville is also the site of the 2017 white supremist rally that turned into a deadly riot. This riot made national news and pushed race conversations into the forefront of American consciousness.

Expect to pay for parking in downtown Charlottesville.

Packing Suggestions

• Jeans or trousers (hiking pants are fine)
• Plain top (long sleeves for winter)
• Jacket or cardigan (for air-conditioned buildings or as a mid-layer in winter)
• Comfortable walking shoes (sandals are good for summer)
• Warm coat, gloves, and hat (winter)
• Small backpack
• Reusable water bottle

Be sure to wear comfortable walking shoes, especially in historic Williamsburg where some streets have cobblestones and you will be walking a lot. You may want to pack a water bottle, sunscreen, and a raincoat.

You can also pack a picnic lunch. Here are some ideas to help with packing food when traveling.

Your Day in Detail

Today, you’ll drive about an hour from Richmond to Colonial Williamsburg. Depending on the day of the week and what time of day you leave Richmond, your drive may take longer if you get caught in morning traffic. 

Pay attention to your route, as some may have tolls and if you don’t have an EZ-Pass, you may need cash or exact change.

Stop at the Colonial Williamsburg Visitor Center and buy tickets. Plan your itinerary, if you haven’t already. Catch the free shuttle to the historic district. 

Most of the outdoor Colonial Williamsburg attractions are wheelchair accessible, but many historic buildings are not. There are accessible restrooms throughout the historic district. Foldable, manual wheelchairs may be rented from the Visitor Center.

Enjoy a morning in colonial Virginia, then eat lunch at one of the many restaurants ranging from fine dining to grab-and-go cafeteria style or sit outside with your packed picnic. Visit one more attraction, then take the shuttle back to the Visitor Center to start the drive to Charlottesville.

Without traffic delays, expect a 2-hour drive from Colonial Williamsburg to Charlottesville. Again, plan your route carefully if you need to avoid tolls. 

After checking in at your hotel, go downtown (expect to pay for parking) and visit Market Street Park. There are websites that can help you plan where to park. 

Market Street Park is important to 21st-century U.S. history. It is the site of the 2017 riot and the site of the statue of Robert E. Lee, removed in 2021, that sparked discussions and protests across the nation and that led to the removal of more statues of Confederate soldiers in Virginia. 

From Market Street Park, it is a short walk to the outdoor Downtown Mall where you can browse shops and eat supper at one of the many restaurants. 

Be aware that there are few benches in downtown Charlottesville and you will need to go to the public library (across the street from Market Street Park), a restaurant, or a convenience store to use the restroom.

Day 3: Charlottesville, Grand Caverns, and Travel Day

About Monticello and Grand Caverns

Monticello was Thomas Jefferson’s plantation home in Charlottesville. You will need to buy tickets if you want to see the house, but parking and walking around some of the grounds is free. 

The Thomas Jefferson Foundation recommends planning at least three hours to explore the grounds and take a house tour.

Grand Caverns, near the town of Grottoes, is a National Natural Landmark and the oldest continually operating show cave in the United States. It is less well-known than Luray Caverns, farther north in Virginia, but it is still a spectacular cave to visit. It is about one hour’s drive north of Charlottesville. 

Reservations are required; you will need to buy tickets in advance. Note that children under age three are not allowed on Grand Cavern tours. Tour lengths range from 70 minutes to four hours. There is no accessibility information on their website.

Packing Suggestions

• Jeans or trousers (hiking pants are fine)
• Plain top (long sleeves for winter)
• Jacket or cardigan (for Grand Caverns)
• Comfortable walking shoes (sneakers are best for the caverns)
• Warm coat, gloves, and hat (winter)
• Small backpack (for Monticello)
• Reusable water bottle (for Monticello)

Be sure to wear comfortable walking shoes. You may also need sunscreen or a rain jacket at Monticello. You will not be allowed to eat or drink in Grand Caverns.

Your Day in Detail

You’ll start the day by driving to Monticello and exploring the grounds while waiting for your tour to start. 

The house at Monticello is accessible to small wheelchairs. Wheelchairs of the correct size are available upon request. Contact Monticello for accessibility questions. 

Monticello has a grab-and-go café, you may bring a picnic to eat on the grounds, or you can grab lunch in Charlottesville.

An alternative to visiting Monticello is walking through the University of VA campus. This is free and will take less time than a visit to Monticello, but nearby parking may be difficult to find, there are no public restrooms, and you may need to search for a pathway that is accessible to mobility devices.

After lunch, drive an hour north to Grottoes, where you will have already reserved a tour time of Grand Caverns. Be sure to wear comfortable shoes and a jacket for the cavern tour. 

After admiring the caverns, head south on the two-hour drive to Farmville, where you can eat supper and window-shop the furniture stores lining Main Street.

Day 4: Farmville

About Farmville

Farmville is in a rural farming community and the home of Longwood University. The town played an important role in the mid-20th-century civil rights movement, as well as being a home of Dorothy Vaughan of Hidden Figures fame. 

Besides locations important to the civil rights movement, the town has live theater, a free art museum (Longwood Center for the Visual Arts), and live music at various restaurants.

There is some street parking and plenty of free parking near downtown, but you may need to walk a few blocks to get from public parking to Main Street. Be alert to parking spots that require a parking permit. 

The town has few benches and some streets are on hills. The shops and restaurants vary in their ability to accommodate wheelchairs. There are public restrooms in the downtown square off of Main Street, but they are sometimes locked. You may need to go to a restaurant or Wal-Mart to find restrooms.

Packing Suggestions

• Hiking pants or trousers
• Plain top (long sleeves for winter)
• Jacket or cardigan (for air-conditioned buildings or as a mid-layer in winter)
• Comfortable walking shoes (sneakers are best for High Bridge Trail)
• Warm coat, gloves, and hat (winter)
• Small backpack (for walking High Bridge Trail)
• Reusable water bottle (for walking High Bridge Trail)
• Hiking snacks

Farmville has a more relaxed, outdoor clothing style than the cities, so dress to be comfortable. Be sure to wear comfortable walking shoes and prepare for the weather when walking High Bridge Trail.

Your Day in Detail

Start your day with a walk on part of High Bridge Trail, a 31-mile-long converted rail bed. 

Instead of walking, you can rent a bicycle from a shop downtown and access the trail right across the street. It is a 4.5-mile (7.2 km) ride to the bridge from downtown. 

If you are walking the trail, drive to the Camp Paradise Road access point and bring cash for the parking fee. From this parking lot, it is an easy walk to the famous bridge – one of the longest recreational bridges in the United States and sitting 125 feet (38 meters) above the Appomattox River. 

Be aware that the Camp Paradise access point only has vault toilets. There are few rest benches along the trail, but it is accessible to wheelchairs that can manage packed sand. 

Picnic on High Bridge or return to Farmville for lunch, then arrive at the R. R. Moton museum by your appointment time. This museum is adjacent to the site of a student walkout to protest poor learning conditions at the all-Black school in the 1950s. This walkout led to Farmville being one of the key destinations in the legal battle for school integration. When you make your reservation, ask about accessibility in the museum.

Take the rest of the afternoon and evening to relax or check out a free music event at Longwood University or a local restaurant. If live theater is more your style, the Waterworks Players may have a play on.

Day 5: Travel Day and Abingdon

About Abingdon

Abingdon is a small arts town in southwest Virginia and is a jumping off point for many outdoor recreational adventures, including the multi-use Virginia Creeper Trail. The town claims to have more restaurants per capita than New York City and offers multiple music venues, being a prime stop along the 300-mile Crooked Road Heritage Music Trail.

Packing Suggestions

• Jeans or trousers (hiking pants are fine)
• Plain top (long sleeves for winter)
• Jacket or cardigan (for air-conditioned buildings or as a mid-layer in winter)
• Comfortable walking shoes (sandals are good for summer)
• Warm coat, gloves, and hat (winter)

Hiking and outdoor apparel will be right at home in Abingdon. Bring a jacket as evenings, even in high summer, can get chilly. Because Abingdon is located at the start of the Virginia Creeper Trail, don’t be surprised to see people of all ages and body types wearing spandex cycling clothes. This mountain town is a down-to-earth, practical place where you should feel comfortable wearing what’s practical and feels good.

Your Day in Detail

After breakfast in Farmville, you’ll drive southwest past Roanoke to Abingdon. Without traffic, this drive takes just under four hours. 

When you arrive in Abingdon, stop by the Visitor Center for a restaurant recommendation, have lunch at one of the town’s many restaurants, then stretch your legs with a stroll down historic Main Street.

Check in at your hotel and have a rest before heading out for supper and a night at the Barter Theatre. You’ll have gotten tickets in advance, so you can park in the theater’s lot and enjoy an evening of regional music. The Barter Theatre has handicapped parking and tickets specifically for seats that accommodate wheelchairs, as well as other assistive options.

Day 6: Travel Day and Grayson Highlands State Park

About Grayson Highlands State Park

Grayson Highlands State Park is near two of Virginia’s highest peaks and offers scenic mountain views of peaks more than 5,000 feet high (1,524 meters). The park is considered the best bouldering site in Virginia and offers access to the Appalachian Trail.

Ponies were introduced in 1974. These small, stocky ponies are wild and should not be approached, petted, or fed, but they are ruggedly beautiful.

This stop is the most rugged and physically demanding of the itinerary.

Packing Suggestions

• Hiking pants or trousers
• Plain top (long sleeves for winter)
• Jacket (consider a water-resistant one)
• Sneakers for hiking
• Warm coat, gloves, and hat (winter)
• Small backpack
• Reusable water bottle
• Hiking snacks – Use this guide on packing snacks in your carry-on for ideas.

Wear clothing and shoes that are comfortable for hiking up a steep mountain. Because of the elevation, you may want sunscreen, even when it’s cloudy. The weather can change quickly on mountain slopes, so check the forecast and be prepared for harsh sun, cold winds, and heavy rain all in the same day.

Your Day in Detail

After breakfast in Abingdon, you’ll drive about an hour to Grayson Highlands State Park. Remember to bring cash for the parking fee. Pick up a map at the payment station, plan your route, and enjoy a steep, beautiful walk up the mountain. Bring hiking snacks and picnic beside the trail while enjoying the mountain views. If you’re lucky, you might see the park’s famous ponies, but don’t feed or pet them!

If you’d prefer not to visit a rugged mountain park that is inaccessible to mobility devices, then an alternate destination is to drive from Abingdon to Roanoke and explore the shops and restaurants downtown. The Roanoke Star is a local landmark that gives a birds-eye view of the city. This park has wide, paved trails that appear to be fully wheelchair accessible.

After a tiring hike, get in the car and settle in for the five-hour drive back to Richmond. You’ll pass by Roanoke and Lynchburg, two of Virginia’s larger cities. These are good places to get gas, use the restroom, and grab a snack. Sheetz is a large convenience store chain in Virginia that typically has clean restrooms, plenty of gas pumps, made-to-order food, and is reasonably safe for women traveling alone.

Day 7: Richmond

About Richmond

Virginia’s capital city has so much to do that the itinerary ends with another day exploring this city. 

Packing Suggestions

For the museums in the morning, jeans/trousers, a nice t-shirt, and sneakers will be fine. For the afternoon, check the weather forecast and dress accordingly.

Your Day in Detail

Today is all about history! Start with the Valentine Museum, which is dedicated to preserving Richmond’s history. Museum tickets include parking validation (free parking) at select parking locations. 

The museum and restrooms are wheelchair accessible. Call ahead for assistance with finding accessible parking. The museum has standard wheelchairs for visitors’ use.

When you’re finished learning about local history, head to The Poe Museum to learn about this famous poet who claimed Richmond as his hometown. There is free off-street parking onsite. 

The Poe Museum’s website says that it is largely wheelchair accessible. When I visited, the museum did not appear to be wheelchair accessible as there are small steps to get into the buildings and space around the exhibits is limited. Their website recommends calling ahead to inquire about accessibility.

The museum’s website says that there are cats in the museum, but I did not see them on my rainy day visit in January 2023. If allergies are a concern, consider calling ahead to find out if the cats will be present.

After learning about Edgar Allan Poe, relax with lunch downtown, then head to your reservation for the Riverfront Canal Cruise. This 40-minute, wheelchair-accessible water tour of Richmond will give you a fresh perspective on the city. 

Afterwards, get some exercise with the 1.25-mile (2 km) Riverfront Canal Walk that goes along the James River. Access points are along almost every block and you will see public art, statues, exhibits, and locals along the way. This is more of a city park and much of the walk is wheelchair accessible, although benches may be few and there are no restrooms.

Try a new restaurant for supper, then head back to the hotel for a relaxing evening before you head home the next morning.

Other considerations when planning a road trip through Virginia

• Virginia does not have a good public transportation system. You will need your own vehicle.
• You will need to pay for parking in many cities, but smaller towns are more likely to have free public parking.
• The best places to find restrooms are in a sit-down restaurant (as a customer), a large gas station like Sheetz or WaWa, or a large retail or grocery store.
• Virginia is beautiful to visit in all seasons, but September and October are especially pretty and a more comfortable temperature than the summer months.

Is Virginia Accessible?

• Virginia is not universally accessible.
• Attractions may be ADA-compliant (Americans with Disabilities Act), but still not be accessible to people using wheelchairs or other mobility devices. I suggest that you call each location and confirm that they can accommodate your needs. 
• You are more likely to find mobility accommodations than assistance with hearing and vision limitations.
• Towns and cities are unlikely to have benches along sidewalks or to have public restrooms.

Now you have an idea of the variety of activities Virginia has to offer! I hope this itinerary gives you a starting point for your road trip in Virginia. To learn more about Virginia tourism, visit Virginia.org.

For a carry-on only packing list, check out our Virginia Packing List post.