Things to Do
Unwind, explore, and connect at Whippoorwill Manor Farm. Enjoy tranquil mornings and breathtaking sunsets, take bike rides or strolls through open fields, or gather with family and friends for meals, games, and cozy evenings by the fireside under the stars.
Ideal for restful getaways or memorable occasions, the farm presents a stunning backdrop to unwind, recharge, and create lasting memories—while remaining close to charming towns, outdoor adventures, and local attractions.
Cycling
For outdoor enthusiasts, the area surrounding Old Rag Mountain provides incredible opportunities for riding and exploration. While the mountain is best known for its challenging hike, the farm and surrounding region feature a network of scenic trails and quiet country roads that are perfect for 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 enjoyable routes—from relaxed, scenic rides to more rugged terrain that offers a bit of a challenge.
The Tour de Madison is an annual road cycling event held in Madison County, Virginia, typically on the third Saturday in May. The ride takes cyclists of all levels through the rolling hills and scenic countryside of the Blue Ridge Mountains, making Whippoorwill Manor Farm an ideal lodging destination for pre- and post-tour events.
Hiking
Step outside and immerse yourself in the beauty of Whippoorwill Manor Farm, where serene walks and open spaces encourage you to slow down and take it all in. Wander through fields, enjoy the fresh air, and cherish quiet moments surrounded by nature—ideal for a relaxing start to your day or a tranquil unwind at sunset.
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. Renowned for its panoramic summit views and thrilling rock scrambles, it offers a rewarding challenge for hikers eager to explore the region’s natural beauty.
Whether you prefer a gentle stroll on the farm or a full-day mountain hike, you’ll discover the perfect blend 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 discover an array of craft breweries, picturesque wineries, and delightful restaurants that showcase the best flavors of the region.
Spend an afternoon enjoying wine with breathtaking mountain views, have a leisurely visit to a nearby brewery, or treat yourself to a memorable meal at a local farm-to-table restaurant. From casual bites to fine dining, there’s something to satisfy every palate.
Downtown Madison features a quaint stretch of historic architecture from the 18th and 19th centuries, many of which are now museums. Driving past the sprawling vineyards and along Main Street feels like stepping back in time, yet it offers enough modern amenities for everyone to enjoy the experience. The towns of Culpeper and Sperryville also provide visitors with plenty to see and do.
Whether you’re planning a leisurely 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 foosball tables, or take the excitement outside with a game of cornhole and volleyball on the lawn.
Fire up the barbecue and relish a relaxed cookout with family and friends, unwind in our sauna, and then gather around the fire pit as the sun sets. Roast s’mores, share stories, and soak in the tranquil country nights under the stars.
Whether you’re playing, grilling, or simply relaxing by the fire, the farm is all about laid-back moments and unforgettable experiences.
