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The Ultimate Guide to a 10-Day Virginia Road Trip



Cape Charles, VA

Welcome to your ultimate guide to exploring Virginia by road! Whether you’re drawn to breathtaking natural landscapes, charming small towns, or historical sites, Virginia offers a blend of attractions sure to enchant every type of traveler. Over the next 10 days, we’ll venture from the shores of Kent Island to the historic streets of Fredericksburg, with lots of incredible stops along the way. Of course keep in mind that I am a nature lover and Korean food addict, so this itinerary caters to those with similar preferences.


Day 1: From Southampton, NY to Kent Island, MD

  • Morning: Set off early from Southampton and head to Kent Island, MD. The drive takes about 5 hours, so pack some good tunes and snacks!

  • Afternoon: Check into a quaint waterfront inn or B&B. I suggest staying here

  • Late Afternoon: Visit Love Point Vineyards for an introduction to Maryland’s wine scene.

  • Evening: Dine at a Knoxie's Table at the Bay Beach Club and enjoy stunning views of Chesapeake Bay.


Day 2: Kent Island to Shenandoah National Park, VA

  • Morning: After breakfast, drive to Shenandoah National Park, a journey of about 3 hours.

  • Afternoon: Settle into your cabin at either Skyland, Big Meadows, or here.

  • Evening: Enjoy dinner at the lodge and prepare for tomorrow's adventure.


Day 3: Waterfalls in Shenandoah National Park

  • Morning: Start your day with a hike to Dark Hollow Falls, one of the park's most accessible waterfalls.

  • Afternoon: Head to Whiteoak Canyon for a series of stunning waterfalls and natural pools.

  • Evening: Return to the lodge for dinner.


Day 4: Exploring Shenandoah

  • Morning: Hike the Stony Man Trail for some of the best views in the park.

  • Afternoon: Take a leisurely drive along Skyline Drive, stopping at various overlooks.

  • Evening: Enjoy an evening of stargazing.


Day 5: Shenandoah to Harrisonburg, VA


Day 6: Harrisonburg to Natural Bridge, VA

  • Morning: Journey to Natural Bridge State Park.

  • Activity: Explore the awe-inspiring Natural Bridge and surrounding trails.

  • Evening: Overnight at the Natural Bridge Historic Hotel.


Day 7: Activities around Natural Bridge

  • Morning: Tour the Caverns at Natural Bridge.

  • Afternoon: Drive to Falling Spring Falls for a relaxing afternoon.

  • Evening: Head to Roanoke, check into a local Airbnb or boutique hotel.


Day 8: Roanoke to Charlottesville, VA

  • Morning: Visit the Roanoke Star and take a hike to Stiles Falls.

  • Afternoon: Travel to Charlottesville, stopping at King Family Vineyards for some wine tasting.

  • Evening: Check into a historic guesthouse or boutique hotel.


Day 9: Explore Charlottesville

  • Morning: Tour Monticello or hike in Ragged Mountain Natural Area.

  • Lunch: Enjoy a meal at Maru or another local Korean restaurant.

  • Afternoon: Drive to Fredericksburg.


Day 10: Fredericksburg to Southampton, NY

  • Morning: Discover Fredericksburg’s rich history and explore Ficklen Island.

  • Afternoon: Begin your return journey to Southampton, NY.

  • Evening: Arrive home with memories to last a lifetime!


This road trip offers a fantastic mix of nature, history, and culture, with comfortable accommodations and plenty of opportunities to sample local flavors. Whether you're a history buff, nature lover, or culinary enthusiast, Virginia’s diverse landscapes and rich heritage promise a rewarding adventure.


*Tips for Travelers:

  1. Packing: Bring comfortable hiking gear and layers for changing weather conditions.

  2. Accommodations: Book your stays in advance, especially in Shenandoah during peak seasons.

  3. Dining: Try to reserve ahead for popular restaurants or vineyards.

  4. Travel: Consider renting a car with good mileage to keep travel costs down.

  5. Waterfalls trail: https://www.virginia.org/things-to-do/outdoors/waterfalls/


Happy travels, and here’s to a wonderful road trip through Virginia!

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