There’s no place quite like Winchester, Virginia in the fall—where crisp mountain air, vibrant foliage, and charming small-town vibes come together for the perfect autumn escape. Whether you're planning a weekend getaway or a cozy day trip, fall is the best time to discover the beauty, flavors, and experiences that make our hometown so special. At Old Town Candle Co., we’re all about capturing the spirit of the season—and we’ve crafted the perfect fall itinerary to help you soak it all in.
Start Your Day at Espresso Bar & Cafe
There’s no better way to kick off your fall adventure than with a warm drink from Espresso Bar & Café, a cozy local favorite nestled in the heart of Old Town Winchester. Whether you crave a classic cappuccino or a seasonal pumpkin spice latte, their artisan brews will give you that comforting, caffeinated hug to start your day right.
Go Apple Picking at Marker-Miller Orchards
Next, head to Marker-Miller Orchards, just a short drive from downtown, for one of Winchester’s most beloved fall traditions: apple picking. Stroll through rows of apple trees bursting with juicy, ripe fruit, and don’t forget to grab a warm apple cider doughnut (or a dozen). It’s the kind of wholesome autumn activity that’s perfect for families, couples, or solo adventurers.
After your orchard visit, make your way back into town for a little shopping at some Winchester favorites. Stop by Scarpa Alta, a stylish boutique offering curated fashion finds, and Kimberly’s, a local institution known for its beautifully curated selection of gifts, home décor, clothing, and gourmet goodies. With their fall-themed displays and locally made products, these shops are the perfect places to find a memento of your trip or start holiday shopping early.
Explore Winchester's Historic Handley Library
Take a moment to slow down and step inside the Handley Regional Library, a stunning Beaux-Arts architectural gem. With its domed rotunda and peaceful reading nooks, this library is a quiet place to rest your feet and take in a piece of Winchester’s rich history. Browse the shelves, flip through a book, or simply admire the beauty of this century-old landmark.
Take a Fall Walk on the MSV Trails
No autumn visit to Winchester is complete without immersing yourself in fall color. Head to the Museum of the Shenandoah Valley (MSV) and explore the beautiful scenic walking trails that wind through woodlands, fields, and gardens. The trees here put on a spectacular show of reds, golds, and oranges—a photographer’s dream and a peaceful way to reconnect with nature.
Wind Down at Valerie Hill Vineyard & Winery
Cap off your day with a glass of wine and a view at Valerie Hill Vineyard & Winery, located in nearby Stephens City. This historic estate offers a relaxed, welcoming atmosphere and award-winning wines perfect for sipping as the sun sets over Virginia’s rolling hills. On the weekends, you might catch live music or one of their popular seasonal events.
Bring the Scent of Fall Home with You
Can’t get enough of that fall feeling? Stop by one of the boutiques who carry Old Town Candle Co. or shop online to take home one of our seasonal soy candles inspired by Winchester’s autumn charm. From “Orchard Trails” to “Sweater Weather”, our hand-poured candles are the perfect way to relive your fall getaway, one cozy evening at a time.
Plan Your Visit to Winchester, VA This Fall
From apple picking and coffee sipping to local shopping and wine tasting, Winchester is the ultimate fall destination in Virginia’s Shenandoah Valley. We can’t wait to welcome you to our corner of the world.
Looking for more local tips and seasonal inspiration? Follow us on Instagram @oldtowncandlecowinc or visit us at oldtowncandleco.shop.