Whether you’re looking for romance, a fun girl’s trip, or a family vacation, we have a 48-hour fall getaway for you! In every corner of Virginia, you can find exciting activities and destinations to create an unforgettable autumn experience. Take a few days off from work to travel or fit an exciting trip into your weekend when you travel to one of these two-day fall getaways.

Northern Virginia Wine Country

Loudoun County is home to 50+ world-class wineries, making it a go-to place for D.C. residents and travelers from all over to experience Virginia’s wine scene. Follow our full itinerary for Touring & Tasting D.C.’s Wine Country, or use the Loudoun Wine Trail Guide to start planning your own custom trip.

Explore Natural Tunnel State Park

Deep in the Heart of Appalachia, Natural Tunnel State Park is filled with vibrant fall foliage. Best of all, the park boasts a chair lift that lets you view the changing leaves from above. Stay overnight in one of the park’s ten mountain ridge cabins, which offer an amazing vantage point for fall’s colors. There are also eight walking trails for guests that want to experience the park at their own pace. Plan an outdoor fall getaway in Scott County with this 48-hour itinerary.

Autumn on the Crooked Road

photo credit: Brian Camp, IG account: @brian_k_camp

The Crooked Road pays tribute to Virginia’s rich musical history while bringing the region’s harmonic heritage to life with nonstop live entertainment. Make Floyd your starting point as it’s the home of the famed Floyd Country Store and its Friday Night Jamboree. The region is ablaze with the changing leaves in the fall, and they can best be experienced with a ride on the Virginia Creeper Trail. Strike out to southwest Virginia for 48 hours of fall fun.

See the Full Autumn on the Crooked Road Itinerary

History, Wine, & Fall Colors Meet in Charlottesville

monticello. photo courtesy of the Thomas Jefferson Foundation

Another one of the impressive wine regions of Virginia surrounds Charlottesville on the Monticello Wine Trail, known as the Birthplace of American Wine. This is a 48-hour getaway you’ll likely want to extend, adding in a visit to the esteemed University of Virginia, Thomas Jefferson’s Monticello, and maybe even a road trip on the scenic Skyline Drive.

Plan a Charlottesville Weekend

Getaway to Southern Style Romance in Lake Country

photo credit:Nomarama IG credit: @_nomarama_

Tranquility reigns supreme in Clarksville, a quiet lake town in Southern Virginia with beautiful foliage, sunrises, and sunsets. Here, tranquility reigns supreme. Spend your 48 hours outdoors on nature trails around Kerr Lake or get out on the water with a rental from Clarksville Marina. After exploring all that nature has to offer in southern Virginia, venture out for some history, scenery, and tasty food using our complete guide to southern style romance.

Natural Beauty: Virginia’s Eastern Shore

photo credit: Johnny Molloy

Spend 48 hours this fall discovering some of the best spots on the Eastern Shore of Virginia. Start at the southern tip and Kiptopeke State Park, an annual stop for migratory birds traveling the Atlantic Flyway. If coming from the north shore, visit Chincoteague and Assateague to see the wild ponies and local wildlife. Outdoor gems are not the only thing that the Eastern Shore has to offer; check out the idyllic port town of Cape Charles as well as several other gorgeous coastal destinations that showcase Virginia’s Chesapeake Bay and the Atlantic shores when you plan a trip to the peninsula.

The Blue Ridge Parkway and the Star City of the South

Roanoke Mill Mountain Star in FallMill Mountain Star (Roanoke). photo credit: Creative Dog Media, IG account: @creativedogmedia

Roanoke is often called the “Star City of the South” due to the 100-foot-tall lighted beacon on Mill Mountain that overlooks the city. Hike up to the star for a breath-taking view of the city, then visit a few of the scenic sites along the nearby Blue Ridge Parkway. There are also a wide variety of museums, restaurants, and outdoor destinations to fill your 48 hours in Roanoke with continuous fall fun.

Historic Triangle Tours 


Discover the Jamestown Settlement, Colonial Williamsburg, and the Yorktown Victory Center and Battlefield when you travel Virginia’s Historic Triangle on the Colonial Parkway. The route’s stunning fall scenery and history abound, creating a great seasonal getaway for those that wish to learn about the Commonwealth’s part in the founding of the nation.

Autumn Splendor in the Cabin Capital of Virginia

photo credit: Jeff Greenough

As the “Cabin Capital of Virginia”, Luray is the perfect destination for a romantic fall getaway. The famous Luray Caverns are beautiful any time of year, and can be toured even on rainy or cooler days. If the weather allows, hike some of the trails in Shenandoah National Park, then go for a drive down Skyline Drive. Surrounded by mountains, you’ll love Luray for a 48-hour autumn escape.

Plan an October getaway to one of these scenic fall destinations to add some autumn excitement to your calendar. Tell us, where is your favorite place to spend 48 hours in Virginia?