Buildings along Beverley St in Downtown Historic Staunton Virginia

These Small Towns in Virginia That Come Alive In The Fall

Nothing says "welcome home!" like the Autumnal gathering of close comrades and kin. On occasion, due to road trip whimsy or a complicated itinerary, an opportunity to cruise through a gorgeous state like Virginia becomes apparent. Village warmth lights up between the Appalachians and the East Coast at this time of year, so whichever slice of heaven (which tastes an odd amount like Pumpkin) you end up in, you will only feel like you have gotten closer to family. To figure out exactly which hamlet has the right fall flavor for you, read on.

Abingdon

Fall colors at the historic Martha Washington Inn in Abingdon, Virginia
Fall colors at the historic Martha Washington Inn in Abingdon, Virginia

Fun Fact: Abingdon is home to the famous Barter Theater, the longest-running professional theater in the nation. Abingdon truly comes alive in the fall, becoming a hub of cultural and outdoor activities. Visitors can experience the annual Abingdon Main Street Autumn Street Fest, which showcases local crafts, food, and music, giving a taste of the local culture. The Virginia Creeper Trail offers an opportunity for hiking, biking, and horseback riding, a perfect opportunity to take in the crisp autumn air. Additionally, the historic downtown area, with its preserved 18th- and 19th-century buildings, is a sight to behold. Events at the William King Museum of Art provide insight into the regional art and culture, while local vineyards and breweries present seasonal flavors for enthusiasts. 

Charlottesville

Historic Court Square in Charlottesville, Virginia
Historic Court Square in Charlottesville, Virginia

In fall, Charlottesville buzzes with an array of activities and events. The town hosts the annual Virginia Film Festival, attracting movie enthusiasts to experience a diverse selection of films and engage with filmmakers. Monticello, the iconic home of Thomas Jefferson, offers tours that provide historical insights amidst the backdrop of colorful autumn foliage. Outdoor enthusiasts can explore the Rivanna Trail or visit Carter Mountain Orchard for apple picking and breathtaking views of the changing leaves. The Downtown Mall, a bustling pedestrian area, becomes a focal point for seasonal events, live music, and local cuisine. Additionally, the numerous vineyards around Charlottesville, like the Pippin Hill Farm & Vineyards, showcase a selection of fall wines and beautiful landscapes. 

Lexington

Historic downtown town city in Lexington, Virginia, via Kristi Blokhin / Shutterstock.com
Historic downtown town city in Lexington, Virginia, via Kristi Blokhin / Shutterstock.com

During this time of year, Lexington's historical architecture and scenic surroundings are accentuated by the vivid fall foliage. You can explore the Stonewall Jackson House or partake in ghost tours revealing the town’s rich history. The nearby Blue Ridge Mountains and the Chessie Nature Trail provide excellent opportunities for hiking and witnessing the spectacular autumn colors. For those interested in equine events, the Virginia Horse Center holds numerous shows and competitions during the fall season. Lexington is also the gateway to the Shenandoah Valley, where numerous vineyards, like Rockbridge Vineyard, open their doors for tastings amidst the autumn scenery. 

Staunton

Staunton, Virginia: American farm with pumpkins harvest, via Kirkam / Shutterstock.com
Staunton, Virginia: American farm with pumpkins harvest, via Kirkam / Shutterstock.com

The birthplace of Woodrow Wilson, the 28th President of the United States, transforms each fall into a foliage haven. The Queen City Mischief & Magic festival transforms the streets into a hub for Harry Potter fans, allowing them to immerse in a world of wizardry. For history buffs, the Woodrow Wilson Presidential Library and Museum offers insights into the life and times of the former president amidst the stunning backdrop of fall foliage. The nearby Shenandoah National Park becomes a canvas of autumn colors, providing ample opportunities for hiking and nature photography. The American Shakespeare Center, based in Staunton, delivers captivating performances, allowing visitors to experience the bard’s plays in a unique setting. The myriad of vineyards in the surrounding area, like Barren Ridge Vineyards, welcome visitors with the taste of harvest wines and scenic views. 

Roanoke

Foggy Appalachian autumn view from the Blue Ridge Parkway, near Roanoke, Virginia
Foggy Appalachian autumn view from the Blue Ridge Parkway, near Roanoke, Virginia

Roanoke’s proximity to the Blue Ridge Mountains makes it a prime location for witnessing the mesmerizing transformation of foliage, especially along the renowned Blue Ridge Parkway. Here, leaf-peepers and hikers can revel in the fiery hues of autumn. The GO Outside Festival in October is a hallmark event, providing myriad outdoor activities and competitions that attract adventurers from near and far.

Downtown Roanoke becomes a bustling scene with the Roanoke Valley’s Craftsmen’s Classic Art & Craft Festival, presenting a vast array of handcrafted items and artworks. For history enthusiasts, the O. Winston Link Museum and the Virginia Museum of Transportation offer deep dives into the region’s rich railroad heritage. Explore Park provides an engaging blend of outdoor experiences and historic attractions, inviting visitors to delve into both the natural and cultural aspects of the area. 

Leesburg

Leesburg. Virginia: Pumpkins, Skeletons and skulls are traditional attributes of Halloween in America, via Kosoff / Shutterstock.com
Leesburg. Virginia: Pumpkins, Skeletons and skulls are traditional attributes of Halloween in America, via Kosoff / Shutterstock.com

Leesburg is a historic town that has been in existence since before the American Revolutionary War and was even occupied briefly by Union forces during the Civil War. In the fall, Leesburg turns into a spectacle of autumnal hues, enriched with various events and historic sites. The town’s historic district becomes even more picturesque with the changing leaves, offering a serene atmosphere for exploring the unique boutiques and dining establishments. Morven Park and Oatlands Historic House and Gardens provide a blend of history and natural beauty, presenting the perfect spots for autumn walks amidst historic structures.

The nearby Tarara Winery and other local vineyards and breweries come alive with fall wine releases and tastings, allowing visitors to savor the flavors of the season. The Leesburg Airshow is a notable event, attracting aviation enthusiasts to witness spectacular aerial displays and demonstrations. The Annual Halloween Parade is another highlight, featuring costumes, floats, and a celebration of community spirit. 

Middleburg

Middleburg, Virginia: central street of the ancient town near Washington, via Kosoff / Shutterstock.com
Middleburg, Virginia: central street of the ancient town near Washington, via Kosoff / Shutterstock.com

Middleburg, with its rich equestrian heritage, is the nation's horse and hunt capital. This town has been a destination for fox hunting and steeplechase events since the 1900s. The town hosts the Middleburg Film Festival, providing film enthusiasts a curated selection of narrative and documentary films in a picturesque setting. The environs of Middleburg offer a range of outdoor activities, including horseback riding through scenic trails adorned with fall foliage and hiking in the nearby Shenandoah Valley.

The charming historic district, with its well-preserved 18th-century architecture, invites visitors to explore boutique shops, galleries, and enjoy local cuisine. Fall fox hunting events uphold the town’s long-standing traditions, offering a glimpse into the local equestrian culture. The numerous vineyards and wineries in the area, such as Chrysalis Vineyards, present opportunities to relish the autumnal flavors amidst the sprawling landscapes.

Floyd

Floyd Country Store, the location of the "Friday Night Jamboree" of old-time string band and bluegrass music, via By Jarek Tuszyński / CC-BY-3.0 & GDFL, CC BY 3.0, https://commons.wikimedia.org/w/index.php?curid=10784353
Floyd Country Store, the location of the "Friday Night Jamboree" of old-time string band and bluegrass music, via By Jarek Tuszyński / CC-BY-3.0 & GDFL, CC BY 3.0, File:Floyd, Va - Country Store.jpg - Wikimedia Commons

Floyd is recognized for its deep musical roots and is home to the famed Floyd Country Store, celebrated for its Friday Night Jamboree. The Floyd County Arts and Crafts Festival is a notable annual event held in fall, displaying a plethora of local crafts and serving as a hub for cultural appreciation. The music scene in Floyd is particularly vibrant during the fall, featuring a variety of musical genres from bluegrass to folk, echoing the town’s rich musical heritage. The surrounding landscapes, accentuated by the colorful fall foliage, are a magnet for those who appreciate nature, offering myriad opportunities for hiking and exploring, especially along the scenic Blue Ridge Parkway. The variety of wineries and breweries, like Chateau Morrisette Winery, offer a taste of local brews and blends, hosting tastings and events throughout the season. 

Front Royal

Beautiful Autumn leaves gather around the gazebo on Main Street in Front Royal, Virginia
Beautiful Autumn leaves gather around the gazebo on Main Street in Front Royal, Virginia

Front Royal is Virginia's northern gateway to the Shenandoah Valley and Shenandoah National Park. The Annual Festival of Leaves is a hallmark event in the town, offering a vibrant array of crafts, food, and music amidst the backdrop of fall foliage. The close proximity to Shenandoah National Park provides boundless opportunities for hiking, wildlife viewing, and photography, allowing visitors to immerse themselves in the breathtaking beauty of the changing seasons. The Skyline Drive, renowned for its panoramic views, becomes a visual feast during the autumn months with its resplendent display of fall colors.

For history enthusiasts, the Warren Heritage Society is a must-see. And for the foodies, the local vineyards and breweries, including the Chester Gap Cellars, host fall tastings, presenting an opportunity to savor the local flavors against the scenic landscapes.

Williamsburg

Folks enjoy an alfresco meal in Merchants Square, a retail and dining area near Colonial Williamsburg, Virginia, via James Kirkikis / Shutterstock.com
Folks enjoy an alfresco meal in Merchants Square, a retail and dining area near Colonial Williamsburg, Virginia, via James Kirkikis / Shutterstock.com

Home to Colonial Williamsburg, this town is a living-history museum presenting a part of the historic district in the city of Williamsburg. The town hosts a range of events like the Harvest Celebration at the Williamsburg Winery, offering a taste of local harvests amidst the cool, crisp air of fall. The historic area of Colonial Williamsburg is a focal point, where visitors can experience the life of the 18th century amidst the brilliant fall foliage, with historical reenactments and interpretations adding to the immersive experience.

The nearby Busch Gardens celebrates the season with the Howl-O-Scream event, combining thrill rides with Halloween-themed festivities. For those interested in culinary delights, the Food & Wine Festival provides a platform to indulge in a variety of gastronomical experiences, featuring local and international cuisines. The amalgamation of historic ambiance, seasonal festivities, culinary delights, and the serene beauty of fall foliage makes Williamsburg a distinctive destination in autumn.

Now that you have experienced the best of a state known for its endless rolling hills and colorful foliage, picking which locales you will visit in person is the easy part. Arriving and staying are also easy parts. Packing your bags and saying hello to the chill of winter might be the only tough eventuality for some, but thankfully, there is beauty to be found in all seasons and all places.

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