Fall Is A Great Time To Escape To Virginia's Charming 'Apple Capital' For A Scenic Getaway

Nestled in Virginia's Shenandoah Valley, Winchester is a town that seems tailor-made for fall getaways. Nicknamed the "Apple Capital," this charming Virginia small town comes alive in autumn. When the air turns crisp, the hillsides glow with plenty of fiery foliage, and orchards brim with fresh fruit ready for picking.

Located about 75 miles west of Washington, D.C., Winchester makes for an easy drive from the city or a quick hop from Dulles International Airport. Booking a rental car would be ideal for transportation, as the drive is about an hour and a half. Plus, Winchester's miles of nature makes for the perfect fall weekend road trip, ideal for urbanites looking to trade high-rises and traffic for mountain views and small-town warmth.

What makes Winchester especially charming this time of year is how seamlessly it blends history, culture, and natural beauty. The Loudoun Street Pedestrian Mall – a brick-paved, walking-only avenue downtown — hums with energy, offering boutiques, breweries, and cafés tucked into historic buildings. Live music drifts through the streets, patios spill over with outdoor dining, and festivals bring locals and visitors together. With its Appalachian roots, scenic backdrop of the Blue Ridge Mountains, and welcoming community spirit, Winchester invites you to slow your pace, linger a little longer, and savor every detail of autumn.

Apple season is king in Winchester, and there's no better way to experience the town's agricultural heritage than by visiting one of its orchards. Marker Miller Orchards is a local favorite, offering more than a dozen apple varieties for picking, along with wagon rides through the rolling countryside. Visitors can sip freshly pressed cider, bite into still-warm homemade donuts, and enjoy wide-open views of the Shenandoah Valley.

While apples are celebrated year-round here, Winchester shines brightest during its seasonal festivals. In spring, the town bursts into bloom with the famous Shenandoah Apple Blossom Festival, a century-old tradition filled with parades, pageants, and fireworks. In autumn, the annual Shenandoah Valley Apple Harvest Festival takes center stage every September, drawing crowds for live music, craft vendors, and a mouthwatering array of pies and local specialties.

But Winchester isn't just about apples — it's also a living museum of American history. Founded in 1744, the town became home to George Washington's office he used in the mid-1750s, and the future president ordered the construction of Fort Loudoun at the north end of town. Winchester also played a key role as a strategic crossroads during the Civil War. History buffs can dive into this layered past at the Museum of the Shenandoah Valley, where $15 admission for adults (or free entry on Wednesdays) unlocks galleries and gardens that glow with autumn color. You can also visit Stonewall Jackson's Headquarters Museum, preserved as it was during the Confederate general's time there. Or simply wander through the streets of Old Town, where brick sidewalks, centuries-old churches, and historic homes offer a glimpse into Winchester's storied past.

Winchester offers everything from charming bed and breakfasts in historic homes to budget-friendly chains near Interstate 81. Expect to pay $150 to $200 per night at mid-range hotels in peak fall. For something special, the George Washington Hotel blends old world luxury with a prime downtown location, while its spa makes for a pampering weekend.

When it comes to dining, Winchester delivers hearty, comfort meals. Head to Oak Stone Craft Pizza and Bar for wood-fired pies; Violino Ristorante Italiano for a cozy, yet high-end European-inspired dinner; or Piccadilly's Public House and Restaurant for pub fare in a restored warehouse from 1900. Don't skip dessert — Red Fox Creamery serves small-batch ice cream perfect for an afternoon stroll.

Heed our essential travel tips for your next leaf-peeping vacation to Winchester. Pack layers for the autumn season: mornings can dip into the 40s, while afternoons climb into the 70s. Bring a camera: the Shenandoah Valley's fall landscapes are some of Virginia's most photogenic. Whether you're apple-picking, wandering cobblestone streets, or sipping cider under gold-colored maples, Winchester promises a bucket-list-worthy fall escape that feels both timeless and effortlessly close to home.