Winchester
Day Trips
Make the most of your day with our curated plans, packed with Winchester's hidden gems and unique experiences!
Start your day by visiting the historic Old Court House Civil War Museum to learn about the region's past. Wander through the charming streets of downtown Winchester to take in the architecture and local shops.
Have lunch at a local café, then take a stroll at the beautiful Handley Regional Library yard. Spend the afternoon exploring the Winchester-Frederick County Convention & Visitors Bureau for more local insights.
Enjoy dinner at a farm-to-table restaurant featuring local produce. Afterward, catch a live performance at the bright and lively Wayside Theatre.
Visit the Shenandoah Valley Discovery Museum to engage with interactive exhibits. Enjoy a leisurely breakfast at a nearby diner before heading to the museum.
Explore local art galleries in the historic district, showcasing regional artists. Break for a late lunch at a pizzeria with unique toppings.
Attend a gallery opening or cultural event at the Bright Box Theater. Dine at a restaurant known for its craft beer and artisanal menu items.
Begin your exploration at the beautiful Jim Barnett Park, where you can take a morning walk and enjoy nature. Bring a picnic breakfast to enjoy under the trees.
Head to the Appalachian Trail for a scenic hike; pack a hearty lunch to fuel your adventure. Experience stunning views and fresh air as you explore the trails.
Return to the city and unwind with dinner at a cozy bistro. If the weather is nice, consider dining al fresco while watching the sunset.
Savor a hearty breakfast at a beloved local café known for its signature dishes. After your meal, stroll through local farmer's markets for fresh goods.
Take part in a cooking class that highlights local ingredients, learning to make a signature dish from the region. Enjoy the fruits of your labor for lunch!
Join a guided food tour that introduces you to various cuisines available in Winchester. End your day with dessert from a local bakery known for its treats.
Visit the Patsy Cline Historic House for a tour and insight into the famous country singer’s life. Don't forget to take a few pictures in the quaint backyard.
Explore the Sunken Road and enjoy lunch at a historic tavern on the way. After that, take a guided tour of the local Civil War Battlefields.
Relax with a movie at the Alamo Drafthouse, which offers a unique dining atmosphere. Grab a late-night snack and enjoy the latest blockbusters.
Rent a bike and explore the scenic trails around Winchester, starting with the Greenway Trail. Enjoy a light breakfast from a local bakery to kick start your energy.
Cycle to the nearby creek for a quiet picnic, taking in the lush scenery. After lunch, visit the local sports facility for some recreational activities.
After a day of biking, enjoy a hearty dinner at a steakhouse. Wind down by relaxing at a nearby brewery for a tasting.
Kick-off the day at the Shenandoah Valley Discovery Museum, which is perfect for kids. Engage them with fun, hands-on exhibits and interactive displays.
Enjoy a family-friendly lunch at a local diner, then head to the park for outdoor games. Spend some time at the playground while the kids burn off energy.
End the day with a family movie night at home or catch a family-friendly show at the local theater. This will be a memorable way to wrap up the day!
Start your day by visiting the lovely Old Town Winchester, known for its boutiques and historic sites. Grab breakfast at a quaint brunch spot in the heart of downtown.
Spend your afternoon exploring the local shops and art stores, picking up unique souvenirs. Break for lunch at a local deli, known for their freshly made sandwiches.
Visit the Winchester Little Theatre for an inspiring show to cap off your day. Enjoy dinner at a gastropub that focuses on local ingredients and craft cocktails.
In the fall, take a scenic drive through the Shenandoah Valley to view the stunning autumn foliage. Stop at a local café for a warm beverage and pastry.
Visit nearby wineries for tastings and educational tours highlighting local viticulture. Enjoy a light lunch with a scenic view amidst the vines.
Dine at a rustic winery restaurant to savor seasonal dishes. Cap off your evening with a relaxed walk through the vineyard as the sun sets.
Begin with a sunrise walk at the George Washington National Forest, capturing breathtaking early morning scenes. Breakfast at a cozy local café is a perfect way to fuel up afterward.
Spend your afternoon photographing the historical sites around Winchester, from the old brick buildings to lush parks. Grab a quick lunch at a food truck for variety.
Find a lookout point for sunset photography, capturing the colors lighting up the sky. Finish with a casual dinner at a restaurant with a view.