Fall is the ideal time to visit the mountains and valley to our west. In our September 2023 issue, we reveal where to go for great hikes and how to see the area by plane or by car. Plus, we’ve found the best places to eat, drink, and shop — and where to kick back and stay awhile.
Positioned along sinuous roads that cut through farmland and wildflower meadows, small towns inhabit the foothills of the Shenandoah and Blue Ridge mountain ranges. Beginning from the north and moving south, we chose five communities where you’ll find excellent restaurants, cool coffee shops, independent boutiques with curated treasures, one-of-a-kind art galleries, and microbreweries and wineries with lively tasting rooms. All offer access to outdoor adventure.
Strasburg, near the northern tip of Shenandoah National Park, is known for its impressive collection of murals that adorn its historic buildings. Each mural tells a story, like Alice Mizrachi’s Poetry in Motion, which speaks to the region’s embrace of diversity and family. Strasburg is minutes from Cedar Creek and Belle Grove National Historical Park — take a guided tour of a stunning 1797-era manor house furnished with period antiques. Afterward, enjoy flights of beer and cider served in vintage film reels at Box Office Brewery, located inside a former movie theater constructed around 1918.
Woodstock, a riverside town with a courthouse designed by Thomas Jefferson, is the fourth-oldest town in Virginia (circa 1772). You can learn about the region’s heritage at the Woodstock Museum. Order a beer at Woodstock Brew House, formerly a Casey Jones clothing factory from the 1920s to 1950s. Pick up picnic provisions for your hike up to Big Schloss at Woodstock Cafe. Locals and visitors alike go paddling and fishing on the Shenandoah River in Seven Bends State Park and climb Woodstock Tower for a bird’s-eye view of the valley. And make sure to grab breakfast or lunch at Woodstock Garden Café, where nearly everything is fresh and local, including coffee from Aperture Coffee Roasters.
Sperryville, poised in the eastern Piedmont region on Route 211, acts as the gateway to Shenandoah National Park’s Thornton Gap entrance and is a short drive to Shenandoah’s most popular hike, Old Rag. It’s hard to believe how many acclaimed restaurants and award-winning vineyards made their homes around Sperryville; likely it’s the lush Rappahannock countryside and the annual Castleton Festival that drew them in. Sperryville is home to Copper Fox Distillery, Thornton River Art gallery, and Thornton River Orchard & Market, making it a destination that checks all the boxes.
Waynesboro is a hub in a wheel of notable destinations. The town is a 10-minute drive from the junction of Skyline Drive and the Blue Ridge Parkway, with close proximity to five spectacular waterfall hikes. Main Street Waynesboro is a 20-minute drive from Staunton and 30 minutes from Charlottesville. In addition to drawing day trippers, hikers, and cyclists, visitors come for Waynesboro’s artsy vibe. It’s home to the
P. Buckley Moss Gallery (a renowned Virginia painter) and Shenandoah Valley Art Center, with two levels of juried artwork by local makers.
Lexington sits near the southern tip of the Shenandoah Valley. The home of the Virginia Military Institute and Washington & Lee University, this classy college town has more upscale restaurants and shops than some small cities. For dinner, two local favorites are Southern Inn and Haywood’s. For cocktails, try Juniper Lounge on the rooftop of The Gin Hotel. Poke around Ladles & Linens for artisan food, kitchen gear, and gifts. For ceramics, check out Earth, Fire & Spirit Pottery. Surrounded by natural beauty, Lexington is only a 20-minute drive from the jaw-dropping Natural Bridge State Park. In addition to luxurious hotels and excellent restaurants and shops, don’t miss taking a carriage ride to see the town’s important historic sites.
Feature image by Renee Sklarew
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