2 Week Virginia Road Trip from Washington DC -

From history and natural beauty to food and wine to arts and culture, Virginia may have more to offer than you realized. This 2 week Virginia road trip itinerary is the perfect way for solo female travelers to get a taste of all the state’s top attractions. Starting and finishing in Washington DC, you’ll explore Shenandoah National Park and the Blue Ridge Mountains, small valley towns, the wine country around Charlottesville, city life in Richmond, and the beaches along the East Coast. Read on for where to go, what to see, where to stay and how to get there.

Table of Contents

2 Weeks in Virginia: A Road Trip from Washington DC

Day 1: Shenandoah National Park

Your first foray out of the city takes you down the scenic curves of Skyline Drive into the northern section of Shenandoah National Park. Many of the park’s best hikes are closer to where you will exit the park tomorrow. For today, set your sights on the Dickey Ridge Loop, a moderate 5-mile double loop that starts and ends at the Dickey Ridge Visitor Center at milepost 4.6 on Skyline Drive.

How to Get from Washington DC to Shenandoah National Park:

Take I-66W for about 1 hour to the Front Royal Entrance Station. Continue along Skyline Drive, making stops at scenic overlooks, hiking trails and picnic grounds as you like.

Where to Stay in Shenandoah National Park:

To camp in this part of Shenandoah National Park, go the Mathews Arm Campground at milepost 22 on Skyline Drive. Sites are $15 a night, but you will need to make a reservation at least six months in advance via recreation.gov.

For more luxurious lodging within the park, continue down to milepost 41.7 on Skyline Drive for the Skyland Lodge. Cabins and traditional rooms start around $120 a night.

If you prefer to stay outside the park, exit the park at milepost 31.5 through the Thornton Gap station. Continue about 10 miles west along Lee Highway until you reach Luray. There are some moderate chain hotels with rooms at $60-70 a night.

Day 2: Luray to Harrisonburg

If you stayed overnight in Shenandoah National Park, you may want to enjoy a little more time on Skyline Drive or the park’s hiking trails. Skyland lodge is very close to one of the park’s best viewpoints, Stony Man Loop, which is just 1.5 miles to the park’s second highest peak.

If you left the park to stay in Luray, you can get a headstart on today’s main attraction: Luray Caverns. These are the largest caverns in the eastern United States, full of stalactites, stalagmites, columns, mud flows and mirrored pools. Tickets are $30 for a one-hour guided tour and the caves are open daily.

From Luray, you’ll head south to Harrisonburg through the Shenandoah Valley. Spend a relaxing afternoon at White Oak Lavender Farm. You can pick your own lavender when blooms are in season, take a self-guided audio tour of the farm, or explore the shop full of bath and body products, aromatherapy goodies, and lavender ice cream. The farm is also home to the Purple WOLF Vineyard and yes – they infuse the wine with lavender.

Other options for things to do in Harrisonburg include the Virginia Quilt Museum and the Edith J. Carter Arboretum and Botanical Garden. Downtown Harrisonburg has a handful of art galleries and interesting boutiques – I’m particularly partial to The Lady Jane, a Jane Austen-inspired shop full of handmade gifts by local artists.

Harrisonburg is also home to Virginia’s First Culinary District. Some top picks include BoBoKo Indonesian Cafe, Cuban Burger, Magnolia’s Tacos & Tequila Bar, Jimmy Madison’s whiskey bar, Bella Luna Wood Fired Pizza, and the Local Chop & Grill House.

How to Get from Shenandoah National Park to Harrisonburg:

Continue along Skyline Drive to Mile 31.5 and exit the park at Thornton Gap. Drive 15 minutes along US-211 W Lee Highway to Luray. After your tour of the caverns, drive another 20 minutes down US-211 W Lee Highway to New Market. Merge onto I-81 S and continue for another 20 minutes before taking exit 247B to Harrisonburg.

Where to Stay in Harrisonburg:

There are plenty of midrange chain hotels in the $50-70 per night arena. You can also find inns and B&Bs in the area like the Friendly City Inn and the Joshua Wilton House, typically around $175 per night.

Day 3: Massanutten Resort

Start your morning in Harrisonburg with brunch. On the weekends, hit up the Clementine Cafe, housed in a historic theater. If it’s a weekday, try Magpie Diner instead.

Spend the rest of the day on a mountaintop splurge at Massanutten Resort. The resort has 14 runs for skiers and snowboarders. A 4-hour session pass is $45 on weekdays and $72 on weekends, with equipment rental available for $42. Other winter options include snow tubing ($25-32 for a 90-minute session) and ice skating ($10 for a 1-hour session).

During the summer, try the resort’s Indoor Water Park or the Adventure Park, which includes a zipline, a canopy tour, ridge rappelling, an indoor climbing wall, and summer tubing. These are all priced a la carte.

Year-round, the Spa at Massanutten offers two-hour massage and aloe vera hydrating treatment packages at $230.

How to Get from Harrisonburg to Massanutten Resort:

Where to Stay in Massanutten:

Overnight accommodations at Massanutten Resort start at $80-90 a night, but if you prefer, the resort is close enough to Harrisonburg to make your visit a day trip and keep your accommodations in town for a second night.

Day 4: Staunton

Downtown Staunton is one of the most charming small towns in Virginia. Enjoy the historic center’s beautiful architecture on a self-guided walking tour. See glassblowing at Sunspots Studio or learn about the history of photography at the Camera Heritage Museum.

History lovers might enjoy the Frontier Culture Museum, featuring reconstructions of traditional farm buildings from different cultures throughout history.

In the evening, make time for the number one must-do in Staunton: the American Shakespeare Center. The theater is the only recreation of the Bard’s indoor Blackfriars playhouse.

How to Get from Harrisonburg to Staunton:

Follow I-81 S for 20 minutes and take exit 225 towards Woodrow Wilson Parkway. Turn left onto Commerce Road and follow it into downtown Staunton.

Where to Stay in Staunton:

Like most Virginia towns, Staunton has a host of chain hotels and historic inns ranging $70 to $120 a night.

Day 5: Waynesboro and Crozet to Charlottesville

The path through the Shenandoah Valley into Charlottesville is jam-packed with craft breweries and wineries.

The Shenandoah Beerwerks Trail spans the valley through Harrisonburg, Staunton and several other regional towns, but your most convenient stop is Waynesboro. There you’ll find Seven Arrows Brewing, Stable Craft Brewing, and Basic City Beer Co.

As you get closer to Charlottesville, you’ll see more breweries like Starr Hill and Pro Re Nata, but you’ll also enter wine country. Near the charming small town of Crozet, you can visit King Family Vineyards, Grace Estate Winery, Stinson Vineyards and White Hall Vineyards. King Family makes some of the best wines in the state and hosts polo matches on Sundays each summer. For a totally unique experience, Indian Summer Guide Service leads horseback rides through the vineyards at King Family and a handful of other wineries near Charlottesville.

While you’re in Crozet, you could also check out local artisans’ work in the historic train depot, or if it’s summertime, pick peaches at Chiles Peach Orchard.

How to Get from Staunton to Charlottesville

Take I-64 E for 10 minutes and pull off at exit 96 for Waynesboro. After your stop in Waynesboro, continue along I-64 E for about 15 minutes, then take exit 107 for Crozet. To reach downtown Crozet, you’ll need to take a left onto US-250 and then another left onto Crozet Avenue. From Crozet, get back on I-64 E for a final 15 minutes, and take exit 121B for Charlottesville.

Where to Stay in Charlottesville

Hotels convenient to downtown Charlottesville are about $150 a night, but if you stay in a mid-range chain hotel close to I-64 or farther up 29 North you could spend closer to $60-80 per night.

One of the nicest and most unique places to stay in Charlottesville is Quirk Hotel – a small boutique franchise with an arts and culture focus. Local artist Kiki Slaughter designed the rooms’ headboards and the hotel has on onsite art gallery where they host exhibition openings and artist talks.

Days 6 & 7: Charlottesville

With two days in Charlottesville, you’ll be able to see quite a bit of the Virginia town I’ve called home all my life. People who come to Charlottesville are often surprised by how well rounded a destination it is. You can experience natural beauty in the Blue Ridge Mountains, a mouthwatering farm-to-table dining scene, a blossoming wine industry, arts, culture and centuries of history.

If you’re on a shoestring budget, check out my list of free things to do in Charlottesville.

Historic Sites in Charlottesville

Charlottesville’s most famous attraction is Monticello, the home of Founding Father Thomas Jefferson. The beautiful, iconic architecture is a big draw, but if you’re interested in local history, make sure you make time for Black history. The new Discover Black Cville Digital Passport makes it easy to experience authentic Black stories from Charlottesville and support local Black-owned and Black-run businesses.

Monticello is now (finally) putting its enslaved laborers front and center, so every tour includes this critical history of the plantation and you do not need to book any separate tickets or special tours to learn about it. In town, you can get a more complete picture of local history at the Jefferson School African-American Heritage Center.

Together with Monticello, the University of Virginia is a UNESCO World Heritage Site (one of the only college campuses in the United States to be designated as such.) UVA’s Rotunda and Lawn are also iconic examples of Jeffersonian architecture, but make sure you explore beyond the main building — the Pavilion Gardens framed by serpentine brick walls are gorgeous in spring and summer! UVA also has a new Memorial to Enslaved Laborers as the University starts to address its full history.

There are other presidential homes near Charlottesville, both of which put a focus on the lives and stories of the enslaved laborers who built this part of the country. James Monroe’s Highland is just down the road from Monticello and James Madison’s Montpelier is about an hour north of town in Orange. Montpelier is home to the phenomenal Mere Distinction of Color exhibit. It’s worth going out of your way for, if you’re a history-focused traveler.

Arts and Culture in Charlottesville

The center of Charlottesville is the Downtown Mall — a brick-laden pedestrian Main Street flanked by local restaurants, galleries, historic theaters and boutiques.

Just a 10-to-15-minute walk away lies my home away from home, the Ix Art Park. Ix is turning the abandoned shell of a former textile factory into a one-of-a-kind immersive art space. The urban outdoor park is covered in murals and sculptures, while inside lies the Looking Glass, a 6000 square foot enchanted forest and kaleidoscopic cavern you can touch and interact with. Ix also hosts events every week from salsa lessons to festivals to a Saturday morning farmers’ market.

Disclaimer: This is not a sponsored post, but I am employed full-time by Ix Art Park.

For more murals, pop on the Charlottesville Mural Project’s interactive map to guide your explorations or grab this self-guided walking tour itinerary of local murals. For a more traditional arts experience, head to a museum or gallery like Kluge-Ruhe Aboriginal Art Collection (the only museum of Indigenous Australian art in the US!), Second Street Gallery, or The Fralin Museum of Art.

Wineries Near Charlottesville

You experienced some of the Monticello Wine Trail earlier in Crozet. If you want to head out for more wine tastings, I recommend going north to Barboursville Vineyards and Early Mountain Vineyards, or sticking close to Monticello and visiting Jefferson Vineyards, Gabriele Rausse Winery, Blenheim Vineyards and Eastwood Farm & Winery. The Monticello Wine Trail also has a handy digital passport to help guide your visits. You could also head south into Nelson County for the ultimate booze traveler’s tour — Route 151 has wineries, craft breweries, cideries and distilleries galore.

Best Hikes Near Charlottesville

You’ve also seen a lot of Shenandoah National Park and the Blue Ridge Mountains already, but if you can’t get enough of Virginia’s natural beauty, Charlottesville is a great base for hikes to Old Rag Mountain, Crabtree Falls, Humpback Rocks and many others.

With only two days in Charlottesville, you won’t be able to see everything. I recommend spending one day downtown and your second day either visiting Monticello and a couple wineries or taking a day hike, depending on your preference.

Days 8 & 9: Richmond

For the next two days, you’ll be enjoying Virginia’s capital. While you’re in Richmond, I highly recommend checking out BLK RVA to celebrate the local Black experience and support Black-owned businesses.

Some of Richmond’s most popular attractions are the Victorian manor and gardens at Maymont, the Lewis Ginter Botanical Garden, and the Virginia Museum of Fine Arts. I also have a soft spot for the Edgar Allan Poe Museum and its charming courtyard in one of the city’s oldest buildings.

Soak up hipster vibes in Carytown. Richmond’s “Mile of Style” is jam packed with indie boutiques, record stores and vintage emporiums. Lots of the city’s amazing street art can be found in Carytown. Follow this self-guided mural tour by Richmond local Gabby Beckford of Packs Light. This is also a great neighborhood to get a taste of Richmond’s dining scene, from craft cocktails to cozy cafes.

For one of the most unique things to do in Richmond, grab a paddle! The James River cuts through downtown Richmond, so you can kayak or paddle board right in the city center.

How to Get from Charlottesville to Richmond

Drive about 1 hour via I-64 E. Take exit 74C for Richmond.

Where to Stay in Richmond

There are plenty of hotels in Richmond around the $100 per night mark. Quirk Hotel has another location here between $150-200 per night. For a luxurious splurge, book the Jefferson Hotel at almost $250 per night.

Day 10 & 11: Williamsburg

As you enter the coastal Tidewater region of Virginia, the most popular things to do are a trio of colonial history sites: Williamsburg, Jamestown and Yorktown.

Williamsburg was a major hub of politics leading up to the Revolutionary War. Today it’s home to an open-air “living history” museum presenting a colonial village with historical shops (like the blacksmith and apothecary), homes, gardens and taverns. Spread over 300 acres, there’s a lot to explore.

Nearby Jamestown was the first permanent English settlement in North America. This attraction is more focused on archaeology, centered around the 1607 James Fort.

Yorktown is the battlefield where George Washington won the Revolutionary War. It will probably only be particularly interesting to major military history buffs.

Spend your second day in the area at Busch Gardens, frequently dubbed the most beautiful theme park in the world. Each section of Busch Gardens is themed after a different European country from the rides to the food to events and performances. Germany features an Oktoberfest-inspired beer hall and Alpengeist, an inverted roller coaster presented as a runaway ski lift, while England stages performances in a recreation of the Globe Theater.

How to Get from Richmond to Williamsburg

Drive 1 hour via I-64 E. Take exit 248 for Williamsburg. Turn right onto VA-143 E and right again on VA-132 S until you reach the Colonial Williamsburg Visitor Center.

Where to Stay in Williamsburg

There are tons of affordable hotels in Williamsburg, around the $50-75 per night mark. There are also more historic inns and B&Bs around $150 per night.

Day 12: Virginia Beach

As you head for the coast, don’t miss the chance to visit one of Virginia’s most important Black history sites. Fort Monroe, near Newport News, is considered both the birthplace and the deathbed of American slavery. The first African enslaved laborers embarked at this point — then known as Point Comfort — in 1619. During the Civil War, this same site became “Freedom’s Fortress” providing a safe haven for thousands of Black laborers escaping slavery. The national monument and its accompanying history museum are free to visit.

When you reach Virginia Beach, you have your choice of waterfront fun. Stroll the 3-mile boardwalk and snap a selfie with the iconic King Neptune statue, climb the Cape Henry Lighthouse or explore the Virginia Aquarium and Marine Science Center. For activities like jet skiing, parasailing, kayaking or paddle boarding, your best hub is Rudee Inlet.

How to Get from Williamsburg to Virginia Beach

Follow I-64 E for about 30 minutes and take exit 268 for Hampton to visit Fort Monroe. Get back on I-64 E for another 15 minutes and use exit 284A to merge onto I-264 E. Follow I-264 E for a final 15 minutes.

Where to Stay in Virginia Beach

First Landing State Park has a great campground for solo female travelers. Campsites are safe but far apart enough for plenty of privacy, and you’ll be inches from one of the area’s quieter beaches.

During peak season in the summertime, most hotels in Virginia Beach are in the $150-200 range.

Day 13: Chincoteague Island

The main attraction in Chincoteague is the area’s wild ponies. They live on Assateague Island within the Chincoteague National Wildlife Refuge. You can see ponies in the wild year-round, but the best time to visit is July when saltwater cowboys round up the ponies and swim them across the channel for auction.

How to Get from Virginia Beach to Chincoteague Island

Follow Shore Drive to the ramp for US-13 N. Pay the toll and drive up US-13 N for about 90 minutes. When you reach Temperanceville, turn right onto State Route 695, then left onto State Route 679, and finally right onto Chincoteague Road.

Where to Stay on Chincoteague Island

Hotels and inns on the island in the summer span $150-250 per night.

Day 14: Return to Washington DC

How to Get from Chincoteague Island to Washington DC

Follow Chincoteague Road to get back onto US-13 N. You will be crossing through Maryland to come into Washington DC from the northern side. Follow US-13 N as it turns into US-50 W for about 90 minutes. Take the ramp to Bay Bridge and merge onto US-301 S/US-50 W. Follow this road for about an hour until you enter the District.

There’s more to explore in Virginia. (For example, in the interest of time, I left off the deep Blue Ridge towns of Southwest Virginia.) For a more complete picture of what to do in the Old Dominion, read my Solo Female Traveler’s Guide to Virginia.