Escape the crowds at Shenandoah National Park and enjoy a tranquil and rewarding hike or bike to Eagle Rock overlook. The Tuscarora Trail is a hidden gem with incredible views of our beautiful valley vistas. We’ll make it easy for you to get magnificent views of our fall foliage – get to Eagle Rock overlook by clicking HERE and hiking about 1.75 miles northeast along the trail, or get to Pinnacle Rock by clicking HERE and hiking from the Biby Trailhead. Mountain biking options are also available in nearby George Washington National Forest.
Take some time to stroll the Loudoun Street pedestrian mall, and its specialty shops and boutiques. This is the heart of Old Town Winchester, with buildings dating back over 275 years. The numerous restaurants here offer outdoor patio dining, and some are heated. If you have children, check out the Shenandoah Valley Discovery Museum in Old Town. The museum is opening a new “sock skating rink” on the rooftop in November 2020.
Spend the afternoon exploring the Museum of the Shenandoah Valley. The museum hosts traveling art exhibitions, in addition to interpreting the history and culture of the Shenandoah Valley. Take time to relax and stroll through seven acres of spectacular gardens, including the favorite Asian garden with its newly opened bamboo grove. The new Trails at the museum open November 25, 2020, and will offer free public access to 90 acres of green space.
Open Friday-Sunday in November and early December, the Family Drive-In Theater offers two screens with new releases and classic favorites, along with a playground for children, car speakers, retro pre-show music, and a concession stand. End your day with an evening of movies under the stars!
You deserve a reward for that amazing hike yesterday, so indulge a little and have breakfast at Bonnie Blue Southern Market & Bakery. Located in a renovated Esso gas station, this very unique and popular spot offers large southern style breakfasts – try the homemade “bacon infused” biscuits, or the award-winning pulled pork with eggs (named one of 13 Essential BBQ Stops by the New York Times)!
LUNCH AND AFTERNOON
Ready for a scenic drive with some farm market shopping and winery hopping? It’s the perfect way to celebrate fall and the harvest season. You can pick and choose how many stops you have time to visit!
Start with Marker-Miller Orchards and Farm Market (closed Sundays in November and December) and make sure to relax in the rocking chairs with an apple cider or pumpkin donut! Two new walking trails around the farm allow you to see beautiful scenery along with cows, goats, and occasional wildlife. Children love their playground.
Then, head to West Oaks Farm Market, where they often feature live music in the heated outdoor courtyard with fire pits. Check out their bakery items, including delicious pies and treats like caramel apples. They also have a bar and grill so you can grab a bite to eat for lunch.
Next stop is James Charles Winery, where you can enjoy a glass of wine by the fireplace, or outdoors on the patio around the fire pit. Enjoy a guided wine tasting or a glass of mulled wine, which is very popular this time of year!
After the winery, visit Richards Fruit Market, located on the Richard’s fifth generation family farm. Their specialty is apples, and we suggest not leaving without trying the apple dumplings, apple pie, caramel apple cookies, apple butter, applesauce…you get the idea. And – if you have children, they will love meeting some of the farm animals.
Finally, end your day at Valerie Hill Vineyard and Winery. This relaxing farm winery offers tastings in a historic 1807 Manor House that has been lovingly restored. Live music is available on weekends, in addition to both indoor and outdoor seating with views of the vines and surrounding countryside.