Things to Do
Unwind, explore, and connect at Whippoorwill Manor Farm. Enjoy peaceful mornings and scenic sunsets, take bike rides or walks through open fields, or gather with family and friends for meals, games, and fireside evenings under the stars.
Perfect for relaxing getaways or special occasions, the farm offers a beautiful setting to slow down, recharge, and make lasting memories—while still being close to charming towns, outdoor adventures, and local attractions.
Mountain Biking
For outdoor enthusiasts, the area surrounding Old Rag Mountain offers incredible opportunities to ride and explore. While the mountain itself is best known for its challenging hike, the surrounding region features a network of scenic trails and quiet country roads perfect for mountain biking and leisurely rides.
Pedal through rolling countryside, wooded paths, and gravel backroads that wind past farms, streams, and breathtaking mountain views. Riders of all skill levels can find routes to enjoy—from relaxed, scenic rides to more rugged terrain that offers a bit of a challenge.
Nearby trail systems and park access points provide even more opportunities to explore the natural beauty of the region, making it easy to spend a full day outdoors. Whether you’re chasing adventure or just enjoying the ride, the landscape around Old Rag delivers an unforgettable biking experience.
Hiking
Step outside and experience the beauty of the land at Whippoorwill Manor Farm, where peaceful walks and open space invite you to slow down and take it all in. Stroll through fields, enjoy the fresh air, and soak in quiet moments surrounded by nature—perfect for a relaxing start to your day or a sunset unwind.
For those seeking a more adventurous hike, Old Rag Mountain—one of the most iconic trails in Shenandoah National Park—is just a short drive away. Known for its panoramic summit views and exciting rock scrambles, it offers a rewarding challenge for hikers looking to explore the region’s natural beauty.
Whether you prefer a gentle walk on the farm or a full-day mountain hike, you’ll find the perfect balance of relaxation and adventure right here.
Explore the Local Charm
Staying at Whippoorwill Manor Farm places you in the heart of a vibrant local food and drink scene. Just a short drive away, you’ll find a variety of craft breweries, scenic wineries, and charming restaurants that showcase the best flavors of the region.
Spend an afternoon sipping wine with mountain views, enjoy a laid-back visit to a local brewery, or treat yourself to a memorable meal at a nearby farm-to-table restaurant. From casual bites to elevated dining, there’s something to satisfy every taste.
Downtown Madison is a short stretch of historic architecture from of 18th and 19th centuries, and many are now museums. Going past the extensive vineyards and driving down Main Street is like traveling back in time, but with enough modern amenities that anyone can enjoy the experience.
Whether you’re planning a relaxed tasting tour or a night out, the area offers the perfect blend of hospitality, flavor, and small-town charm—making every outing just as enjoyable as your stay.
In House Activities
There’s no shortage of ways to enjoy your time at Whippoorwill Manor Farm. Head to the game room for friendly competition and indoor fun on our professional shuffleboard and fooseball tables, or take things outside with a game of cornhole and volleyball on the lawn.
Fire up the barbecue and enjoy a laid-back cookout with family and friends, relax in our sauna, and then gather around the fire pit as the sun sets. Roast s’mores, share stories, and soak in the peaceful country nights under the stars.
Whether you’re playing, grilling, or simply unwinding by the fire, the farm is all about easygoing moments and memorable experiences.
