Road tripping through Virginia with Kids

There must be something about living in Rhode Island, the smallest state in the country, that made me think that if I spent two weeks exploring Virginia I could see it all. Not even close. There is so much to do in Virginia with kids that it might take a lifetime to explore — from historic sites to beaches to mountains and rivers to underground caverns. So instead of trying to do it all, I decided to visit just a few key towns on a two-week road trip through Virginia.

Traveling from Rhode Island, with an overnight stop in New Jersey, we made a big loop through the state. We came down Highway 13 through the Delmarva (Delaware / Maryland / Virginia) peninsula and across the Chesapeake Bay Bridge Tunnel to our first stops in Hampton and Newport News. From there, we continued across Interstate 64 with stops in Williamsburg/Jamestown and Charlottesville. We then drove a piece of the Skyline Drive 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 before continuing up 81 with a stop in the Pocono Mountains in Pennsylvania on the way home.

While I will be writing about all the stops along our two-week, mother-daughter road trip, I thought it might be helpful to provide our full itinerary for those considering a similar Virginia road trip or those who just want to get a better sense of some of the things to do in Virginia with kids.

Virginia with Kids: A Two-Week Roadtrip Itinerary

Two-week road trip through Virginia with kids -- what to do and where to stay

Day 1 — Arrive in Virginia

  • Arrive in Hampton, Virginia (alternatively you could start off in Virginia Beach if you can add in a few extra days) and check in to the Hilton Garden Inn Hampton Coliseum Central in Hampton, VA.
  • Stop for dinner at Six Little Bar Bistro in the Phoebus neighborhood for tapas or check out some of the restaurants near the hotel.

Day 2 — Hampton, Virginia

  • Breakfast at the hotel (they have the friendliest staff!)
  • 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)
  • For lunch, take a break from learning and enjoy some time in the sun at the Paradise Ocean Club. You can have a casual lunch at their restaurant and then pay at small fee to gain beach and pool access.
  • 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.
Orion test module at the Virginia Air and Space Center in Hampton, VA

Virginia Air and Space Center in Hampton, VA

Day 3 — Hampton, VA

  • After breakfast, head over to the harbor front to board the Miss Hampton II Cruises tour boat for a three-hour cruise and tour of Fort Wool.
  • 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)
  • Finish off the day with dinner at The Point at Phoebus, a restaurant that focuses on locally grown and sourced foods.
  • 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.)
 The National Mariners' Museum -- What to do in Virginia with Kids

The National Mariners’ Museum in Newport News, VA

Day 4 — Newport News, VA

  • 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 — Busch Gardens or Watercountry USA, Williamsburg, VA

Get a break from sightseeing with some family fun at either Busch Gardens Williamsburg or Water Country USA  in nearby Williamsburg! If amusement or waterparks aren’t your thing, spend the day in Colonial Williamsburg.

Day 6 — Jamestown, VA

Jamestown Settlement -- What to do on a road trip through Virginia with Kids

The Powhatan Village at Jamestown Settlement

  • 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 Williamsburg. After dinner stop by the Wythe Candy & Gourmet Shop for a treat. Stay in Williamsburg or drive two-and-a-half hours to Charlottesville and check in to The Graduate Hotel, right across from the University of Virginia.

[Note: If you have an extra day or two, be sure to add Colonial Williamsburg to your itinerary. We were only able to spend a couple of hours exploring and there is so much more to see! You may also want to schedule one to two days in Richmond before hitting Charlottesville.]

Day 7 — Charlottesville, VA

  • 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 plantation and 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.
Carter Mountain Orchard in Charlottesville -- What to do on a road trip through Virginia with Kids

Enjoying the view at Carter Mountain Orchard in Charlottesville

Day 8 — Charlottesville, VA

  • Start off with a bit more history with a visit to Ash Lawn-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 Dr through Shenandoah National Park (allow two to four hours) before bedding down at the Residence Inn Harrisonburg. If you can, try to extend your trip to spend at least a full day hiking in the park.
Bear in Shenandoah National Park

We spotted a bear in Shenandoah National Park

Day 9 — Harrisonburg, VA

  • 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 (James Madison University is located here).
  • 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.
  • We spent the next few nights at a vacation rental in Woodstock (Virginia), so we spent the rest of our day recharging at our cabin in the woods.
  • Stop for dinner at Jalapeños Southwest Grill in Harrisonburg or, if you are in Woodstock, try Joe’s SteakHouse.
Kline's dairy bar ice cream

Cooling off with ice cream from Kline’s Dairy Bar in Harrisonburg

Day 10 — Woodstock, VA

  • 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 with Route 11 Outfitters. (Allow for two to three hours)
  • After cleaning up, head up to Strasburg for dinner at either Christina’s Cafe or Jalisco Mexican Restaurant.

Day 11 — Woodstock, VA

Shenandoah Caverns: What to do in Virginia with kids

  • Head over to Bryce Resort in in Bayse for some ziplining, grass tubing, or other adventure (or skiing in the winter!). (Allow half a day)
  • Have lunch at Bryce and then 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)
  • 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.

Day 12 — Winchester, VA

Winchester, VA -- What to do in Virginia with kids

If you can spend a full two weeks in Virginia, I’d recommend adding another day in Colonial Williamsburg and Shenandoah National Park.


Virginia with kids a two-week road trip itinerary with stops in Hampton, Newport News, Williamsburg, Jamestown, Charlottesville, Shenandoah National Park, Harrisonburg, Woodstock, and Winchester

There is so much more that we didn’t get a chance to see. What are your favorite spots in Virginia?

Mentioned in this post
  1. Six Little Bar Bistro
    Restaurant in Hampton Virginia

    6 E Mellen St
    Hampton Virginia
    (757) 722-1466
  2. Hampton History Museum
    Attraction in Hampton Virginia

    120 Old Hampton Ln
    Hampton Virginia
    (757) 727-1610
  3. Virginia Air & Space Center
    Attraction in Hampton Virginia

    600 Settlers Landing Rd
    Hampton Virginia
    (757) 727-0900
  4. Paradise Ocean Club
    Attraction in Virginia

    490 Fenwick Rd
    (757) 224-0290
  5. Bluebird Gap Farm
    Attraction in Hampton Virginia

    60 Pine Chapel Rd
    Hampton Virginia
    (757) 727-6739
  6. The Deadrise
    Restaurant in Hampton Virginia

    100 McNair Dr
    Hampton Virginia
    (757) 788-7190
  7. Miss Hampton II Cruises
    Attraction in Hampton Virginia

    710 Settlers Landing Rd
    Hampton Virginia
    (757) 722-9102
  8. Venture Kitchen & Bar
    Restaurant in Hampton Virginia

    9 E Queens Way
    Hampton Virginia
    (757) 325-8868
  9. Casemate Museum of Fort Monroe
    Attraction in Hampton Virginia

    20 Bernard Rd
    Hampton Virginia
    (757) 788-3391
  10. The Point at Phoebus
    Restaurant in Hampton Virginia

    30 E Mellen St
    Hampton Virginia
    (757) 224-9299
  11. Courtyard by Marriott Newport News Airport
    Hotel in Newport News Virginia

    31 Saint Johns Road
    Newport News Virginia
  12. Virginia Living Museum
    Attraction in Newport News Virginia

    524 J Clyde Morris Blvd
    Newport News Virginia
    (757) 595-1900
  13. Taste Unlimited
    Attraction in Newport News Virginia

    702 Mariner Row
    Newport News Virginia
    (757) 596-8651
  14. The Mariners' Museum
    Attraction in Newport News Virginia

    100 Museum Dr
    Newport News Virginia
    (757) 596-2222
  15. Paragon City Center 12
    Attraction in Newport News Virginia

    11810 Fountain Way
    Newport News Virginia
    (757) 525-9898
  16. Newport News Park
    Attraction in Newport News Virginia

    13560 Jefferson Ave
    Newport News Virginia
    (757) 886-7912
  17. Pelican's SnoBalls
    Restaurant in Newport News Virginia

    11075 Warwick Blvd
    Newport News Virginia
    (757) 532-1492
  18. Busch Gardens Williamsburg
    Attraction in Williamsburg Virginia

    1 Busch Gardens Blvd
    Williamsburg Virginia
    (800) 343-7946
  19. Water Country USA
    Attraction in Williamsburg Virginia

    176 Water Country Pkwy
    Williamsburg Virginia
    (757) 229-9300
  20. Colonial Williamsburg Visitor Center
    Attraction in Williamsburg Virginia

    101 Visitor Center Dr
    Williamsburg Virginia
    (757) 229-1000
  21. Jamestown Settlement
    Attraction in Williamsburg Virginia

    2110 Jamestown Rd
    Williamsburg Virginia
    (757) 253-4838
  22. Historic Jamestowne
    Attraction in Jamestown Virginia

    1368 Colonial National Historic Pkwy
    Jamestown Virginia
    (757) 229-4997
  23. Wythe Candy & Gourmet Shop
    Restaurant in Williamsburg Virginia

    414 W Duke of Gloucester St
    Williamsburg Virginia
    (757) 229-4406
  24. Charlottesville
    City in Virginia

    Charlottesville Virginia
  25. Michie Tavern
    Attraction in Charlottesville Virginia

    683 Thomas Jefferson Pkwy
    Charlottesville Virginia
    (434) 977-1234
  26. Monticello
    Attraction in Charlottesville

    931 Thomas Jefferson Pkwy
  27. Carter Mountain Orchard
    Restaurant in Charlottesville Virginia

    1435 Carters Mountain Trail
    Charlottesville Virginia
    (434) 977-1833
  28. Ash Lawn-Highland
    Attraction in Charlottesville Virginia

    2050 James Monroe Pkwy
    Charlottesville Virginia
    (434) 293-8000
  29. Tavern On the James
    Restaurant in Scottsville Virginia

    280 Valley St
    Scottsville Virginia
    (434) 286-3500
  30. James River Reeling & Rafting
    Attraction in Scottsville Virginia

    265 Ferry St
    Scottsville Virginia
    (434) 286-4386
  31. Skyline Dr
    Rileyville Virginia

    Skyline Dr
    Rileyville Virginia
  32. Residence Inn Harrisonburg
    Hotel in Harrisonburg Virginia

    1945 Deyerle Ave
    Harrisonburg Virginia
    (540) 437-7426
  33. Harrisonburg Farmers Market
    Restaurant in Harrisonburg Virginia

    228 S Liberty St
    Harrisonburg Virginia
    (540) 476-3377
  34. James Madison University
    Attraction in Harrisonburg Virginia

    800 S Main St
    Harrisonburg Virginia
    (540) 568-6211
  35. Rockingham County Fair
    Attraction in Harrisonburg Virginia

    4808 S Valley Pike
    Harrisonburg Virginia
    (540) 434-0005
  36. Klines Dairy Bar - South Main
    Attraction in Harrisonburg Virginia

    2425 S Main St
    Harrisonburg Virginia
    (540) 434-4014
  37. Woodstock (Virginia)
    City in Virginia

    Woodstock (Virginia) Virginia
  38. Woodstock Cafe & Shoppes
    Restaurant in Woodstock Virginia

    117 S Main St
    Woodstock Virginia
    (540) 459-8888
  39. Woodstock Tower
    Attraction in Shenandoah County Virginia

    Woodstock Tower Trail
    Shenandoah County Virginia
  40. Bryce Resort
    Shenandoah County Virginia

    Bryce Resort
    Shenandoah County Virginia
  41. Route 11 Potato Chips
    Restaurant in Mt Jackson Virginia

    11 Edwards Way
    Mt Jackson Virginia
    (540) 477-9664
  42. Shenandoah Caverns
    City in Virginia

    Shenandoah County Virginia
  43. Toms Brook
    City in Virginia

    Shenandoah County Virginia
  44. Winchester (Virginia)
    City in Virginia

    Winchester (Virginia) Virginia
  45. Shenandoah Valley Discovery Museum
    Attraction in Winchester Virginia

    19 W Cork St
    Winchester Virginia
    (540) 722-2020
  46. Museum of the Shenandoah Valley
    Attraction in Winchester Virginia

    901 Amherst St
    Winchester Virginia
    (540) 662-1473
  47. Harpers Ferry
    City in West Virginia

    Harpers Ferry West Virginia
  48. Bavarian Inn
    Hotel in Shepherdstown West Virginia

    164 Shepherd Grade Rd
    Shepherdstown West Virginia
    (304) 876-2551

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17 Comments on “Road tripping through Virginia with Kids

  1. Thanks for sharing! So need to do this area with my kids but wanted to do Washington too.

      That is a nice add in — pick and choose but hopefully some pieces of this will provide some helpful ideas.

    Tamara, I love the T-shirts (whose idea was it?). Pinning this post for possibly later in school year for trips of Virginia college towns:)

      My idea but we both loved them and it was fun to see people’s reactions. Funny you mention about college towns because I drove through campuses to get a sneak peak while we were in the area!

    It is so awesome that you took a road trip with just you and your daughter! I’m sure those are some pretty special memories. 🙂

      And the good news is she wants to do it every year!

    Virginia is such a beautiful state, and I love the diverse array activities that you included in your itinerary!

    What a fun experience for you and your daughter – you had a busy two weeks! I have long wanted to visit Colonial Williamsburg but I had no idea that there was so much else to do in the state as well. I might have to plan for more than a weekend trip!!

      If you do Williamsburg definitely leave time for Jamestown as well.

    What a great itinerary! We did Virginia in about 5 days and definitely missed things.

    What a thorough itinerary! Love those t-shirts. 🙂

      Thanks, they were a big hit!

    Very nice itinerary. If you want to include Washington DC in your road trip there are loads of great parks, hikes, and other interesting stops in my area—Northern Virginia. Maybe time for another Virginia visit? 🙂

      Definitely– this was a bit more off the beaten path

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