How to Plan a Virginia Road Trip with Kids (7-14 Day Itinerary)

Living in Rhode Island, we have taken many east coast road trips over the years as we slowly tick off all of the States. Coming from such a small state, it is hard to imagine that you would need at least a week to properly explore Virginia, but Old Dominion is larger than you think. With important historical sites like Colonial Williamsburg, Jamestown, and Monticello and natural wonders like Shenandoah National Park, the Blue Ridge Parkway, and Virginia Beach, you will want to take your time and plan a Virginia road trip that encompasses a bit of everything.

The easiest way to see the highlights on a Virginia road trip is to take a circular route through the state, starting in Norfolk, Virginia and ending in Washington D.C. (which you should also tack on a few days to see if you haven’t visited yet.) Since we were traveling from New England, instead of flying we drove down Highway 13 through the Delmarva (Delaware / Maryland / Virginia) peninsula and across the Chesapeake Bay Bridge Tunnel to our first stops on our mother-daughter Virginia road trip.

From there, we continued across Interstate 64 with stops in Williamsburg/Jamestown and Charlottesville. We then drove through Shenandoah National Park and then continued up Interstate 81, with stops along the Shenandoah Valley in Harrisonburg, Woodstock, and Winchester. We finished up just across the border in Harper’s Ferry, West Virginia, but it is easy to circle back to Washington D.C. for a flight home.

Virginia Road Trip Itinerary

When planning your Virginia road trip, you can shorten this itinerary to fit into a one-week trip or extend it with more time at each stop for a full two-week vacation.

• Day 1: Arrive in Norfolk, Virginia
• Day 2-4: Virginia Beach, Hampton, and Newport News
• Day 5-7: Williamsburg and Jamestown
• Day 8-9: Charlottesville
• Day 10-12: Shenandoah Valley

This map was created using Google My Maps and covers your Virginia road trip itinerary above. You can click on the star next to the title and save this to your Google Maps account or click on the share icon to send it to yourself via email.

Day 1: Arrive in Norfolk / Virginia Beach

Note: This post may contain affiliate links. If you click a link and make a purchase, I may receive a small commission. All opinions are my own.

Editor’s Note: Part of our trip was hosted by Visit Hampton, Newport News, Visit Charlottesville, Shenandoah County, and Visit Harrisonburg. All opinions are my own.

If you plan on flying to Virginia and renting a car, for this itinerary it is best to fly into Norfolk, Virginia (you can get great deals on Breeze Airlines from a number of cities) and out of Washington D.C. (Dulles or Reagan National). Alternatively, you can fly into and out of D.C. and make a loop.

If you have at least 10 days for your Virginia road trip and you are visiting during the warmer months, I’d suggest spending at least your first night or two in Virginia Beach. However, if you aren’t looking for a beach vacation, head straight to either Hampton, Virginia or nearby Newport News to have a home base for your first few days of exploration.

Where to stay: Hilton Garden Inn Hampton Coliseum Central in Hampton, VA or the Courtyard by Marriott Newport News.

Day 2: Hampton, Virginia

Hampton, Virginia is an under-the-radar destination for history buffs. With the Naval station just across the bay, Hampton sits at the entrance of important waterways and has played an impactful role in U.S. history, from its negative history as a landing spot for colonists and the first place that captured Africans were brought to America and enslaved to work the growing tobacco plantations to its more positive history as a NASA Research Center that earned its “sea to the stars” motto through its critical role in sending men to the moon.

There is so much to see and do in Hampton that you can easily spend two to three full days exploring its rich history. On your first day, I’d recommend:

• Visit the Hampton History Museum for some insight on all the area’s fascinating history from the early colonists to the first astronauts. (Allow one hour)
• Take a stroll to the nearby Virginia Air & Space Center with a stop first to ride Hampton’s antique carousel. Enjoy learning about the history of flight and the manned space program and take in an IMAX show, included in your ticket. (Allow one to two hours)
• If it is not a beach day, stop at the Bluebird Gap Farm to play on the playground and meet their resident farm animals or just head back to the hotel for a short swim in the small pool.
• Head over to Fort Monroe for dockside dining at The Deadrise.

Read more: Things to do in Hampton, Virginia

Day 3: Hampton, Virginia

If you have time for a second day in Hampton, there is still more to see. I would recommend:

• After breakfast, head over to the harbor front for a tour boat cruise on the Hampton Queen.
• Walk over to Venture Kitchen & Bar in downtown Hampton for lunch on their wood-grilled pizzas and homemade tater tots.
• Tour the Casemate Museum of Fort Monroe and Fort Monroe to see the place where the first African slaves arrived in the U.S. and the cell where Jefferson Davis was imprisoned after the Civil War. Other famous soldiers stationed here include Edgar Allen Poe and Robert E. Lee. (Allow one to two hours)
• Either head over to Newport News to check in to the Courtyard by Marriott Newport News Airport, or extend your stay  at the Hilton Garden Inn (it is only 20-30 minutes away.)

Day 4: Newport News, Virginia

If you are short on time, you could combine some Newport News attractions with your time in Hampton, but there are a couple of gems here that your kids will love.

• Start your day at the Virginia Living Museum, which houses more habitats, wildlife and plant species than would be encountered in a lifetime of outdoor adventures in Virginia. It’s here that you can walk through an Appalachian mountain cove and a southeastern cypress swamp, touch a horseshoe crab or a sea star, go eye-to-eye with a red wolf and a bald eagle and watch otters frolic on the outdoor natural trail!  (Allow two hours)
• Stop for lunch at Taste Unlimited at City Center in Oyster Point and enjoy a stroll around the fountain, stopping to pose for a photo at the Love NN sign.
• Next up, visit the The Mariners’ Museum. The real highlight here is the U.S.S. Monitor Center — be sure to stop into the Battle Theater for a great overview of the battle of the Ironclads at Hampton Roads. Also check out the detailed craftsmanship on the miniature ships in the Great Hall of Steam. (Allow two hours)
• For dinner you might want to head back to the City Center, where there are plenty of family-friendly options to choose from.
• After dinner, check out a movie at the Paragon City Center 12 in City Center or head over to Newport News Park for a walk or a hayride. Stop at Pelican’s SnoBalls for a snowcone dessert.

Day 5: Williamsburg, Virginia

If your kids need a break from history and sightseeing, enjoy some family fun at either Busch Gardens Williamsburg or Water Country USA. However, you really shouldn’t miss spending a day in Colonial Williamsburg. If you can manage three to four days in the Williamsburg area, that would be ideal.

Read more: How to spend a day in Colonial Williamsburg

Where to stay: Williamsburg Inn or Club Wyndham Kingsgate

Day 6: Jamestown & Yorktown, Virginia

This area is so rich with early U.S. history that you will want to spend a day visiting both Yorktown and Jamestown to learn more about colonial and revolutionary history:

• Start off with a visit to Jamestown Settlement. This attraction has recreated the original Colonial fort, offers an interactive representative Powhatan village, and has three ships that are replicas of the ones that Captain John Smith and the original settlers used to travel to the New World. There is also a very good museum on site and a cafe for lunch, so plan to spend at three hours.
• Visit Historic Jamestowne, the location of the original fort where English settlers first colonized Virginia. Here you will see the outline of the original fort, some ruins from the town, and the archeological digs where they are still unearthing artifacts from the 17th century. (Allow one to two hours)
• Finish your day with a visit to the American Revolution Museum at Yorktown.
• After dinner drive two-and-a-half hours to Charlottesville.

Read more: Jamestown Settlement vs. Historic Jamestowne, Which is Better?

Day 7: Charlottesville, Virginia

Charlottesville is home to the University of Georgia and two of the Founding Fathers including Thomas Jefferson and James Monroe. In addition to historical sites there are wineries and natural attractions nearby.

• Spend the morning exploring downtown Charlottesville. The pedestrian mall offers a great selection of shops and restaurants.
• Head out to Michie Tavern for an all-you-can-eat colonial mid-day meal of fried chicken, pulled pork, baked chicken, mashed potatoes and gravy and more! Allow time to visit the tavern museum and explore the quaint shops next door. Kids might enjoy the scavenger hunt and win a candy stick to boot! (Allow two hours)
• After lunch, head up to Monticello, Thomas Jefferson’s home. Purchase tickets in advance for the tour of your choice and learn all about our nation’s third president. (Allow two to three hours)
• To relax after all that history, stop by Carter Mountain Orchard, just down the road, and have a run around their lawn overlooking Charlottesville and the valley while sampling some of their fresh produce, baked goods, or cider. On Thursday evenings in the summer you can also enjoy a free music concert on the lawn and visit the snack bar for a light bite to eat.

Read more: Things to do in Charlottesville, Virginia with kids

Where to stay: The Graduate Hotel Charlottesville

Day 8: Charlottesville, Virginia

If you have time, there is plenty more to do in the Charlottesville area including:

• Start off with a bit more history with a visit to Highland, home of James Monroe, fifth president of the United States. (Allow one to two hours)
• Get ready to head out of town to nearby Scottsville and stop for lunch at Tavern On the James.
• After all that history, it is time to relax and enjoy nature with a kayak or raft down the James River with James River Reeling & Rafting (or you could sneak in a little wine tasting nearby!) (Allow three hours)
• At this point, we headed out for a drive on the Skyline Drive through Shenandoah National Park (allow two to four hours) to Harrisonburg. If you can, try to extend your trip to spend at least a full day hiking in the park.

Where to stay: Residence Inn Harrisonburg

Day 9: Harrisonburg, Virginia

While it is easy to spend a few days hiking in Shenandoah National Park, there are many cute towns and attractions to see in Shenandoah Valley. Harrisonburg is home to James Madison University and this small college town is a good place to stay when visiting Shenandoah. If you are short on time, you can skip Harrisonburg and head straight to Woodstock.

• If you are there on the weekend, start your day at the Harrisonburg Farmers Market downtown and then spend some time exploring this college town.
• We visited the Rockingham County Fair in the afternoon, but if that isn’t going on, there are some nearby hikes, caverns, or arboretums to explore. You may also want to head back to Shenandoah National Park for the afternoon.
• Be sure to stop at Klines Dairy Bar on the way out of town for their famous custard-style ice cream.
• From Harrisonburg, drive up to the small town of Woodstock.

Where to stay: Cabin rentals in Woodstock

Day 10: Woodstock, Virginia

Woodstock is a cute small town in the heart of the Shenandoah Valley, making it a perfect home base for exploring the caverns, river, and local attractions for a day or two.

• Start your day with breakfast at the Woodstock Cafe & Shoppes then head up the mountain to the Woodstock Tower for beautiful views of the valley.
• Get ready for some more fun in nature with a rafting or kayaking trip on the Shenandoah River. (Allow for two to three hours) OR,
• Head over to Bryce Resort in in Bayse for some ziplining or other adventures. (Allow half a day)
• After lunch, stop off at Route 11 Potato Chips to taste test their different flavors and see how they process over 14,000 pounds of potatoes a day. (Allow 15 minutes)
• Nearby, visit Shenandoah Caverns and be prepared to be wowed by room after room of rock formations. Afterwards, stop in at their other attractions, including American Celebration on Parade, an impressive collection of parade floats. (Allow two hours)
• Finish up with a casual dinner at the Woodstock Brewhouse.

Read more: 10 Fun and adventurous things to do in Shenandoah Valley

Day 11: Winchester, Virginia

Founded in 1744, Winchester is the oldest Virginia city west of the Blue Ridge Mountains. Known as the Apple Capital, there are plenty of farms nearby to visit, along with a charming downtown with historic sights and a pedestrian mall.

• Make a stop at the Posey ThisIsIt Llama Farm in Toms Brook to meet their many, friendly llamas. (Allow one hour)
• Drive up to Winchester (Virginia) for lunch on the pedestrian mall.
• Spend some time exploring the scenic downtown, with possible stops at the Shenandoah Valley Discovery Museum for kids 10 and under or the Museum of the Shenandoah Valley.
• At this point we headed up to Harpers Ferry, West Virginia and spent the night at the Bavarian Inn in Shepherdstown, however, it is only an hour and a half drive to Washington D.C.

Read more: 3 Days in Washington D.C. itinerary

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