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Reserve My Stay



For appointments, please contact 855.290.5677

Reservations Office Hours:

Monday - Friday: 8:00 AM - 7:00 PM
Saturday & Sunday 8:00 AM - 6:00 PM




Group Tours

  • Countryside Trail Rides: Experience the natural beauty of Middleburg’s famed hunt country astride docile trail horses as we meander through the woods and fields at a leisurely walk. 
    • 1 hour ride | Minimum of 3 weeks notice for reservation of up to 4 horses | No prior riding experience required, weight limit is 220lbs
  • Guided Nature Hike: Join an area naturalist and learn about the beautiful flora and fauna of the mid- Atlantic in every season – including fall foliage and winter wonderland. Bring your camera so you don’t miss one picture-perfect moment.
  • Middleburg History Walking Tour: Enjoy a historic tour of Middleburg showcasing the National Sporting Museum and Library, America’s oldest running Inn, the Jacquelyn Kennedy Pavilion and other landmarks while learning about the area’s history dating back to the 1700s.
  • Hike & Brew: Join a recreation team member for a 1.5 mile hike on our property to Lost Barrel Brewing! Once we reach our destination, enjoy a flight of Lost Barrel beer.
  • Winery Tours with Osborne Events: Enjoy guided tastings at your choice of more than 80 wineries throughout Northern Virginia’s Wine Country, a region renowned for its Cabernet Franc, Cabernet Sauvignon, Chambourcin, Chardonnay, Mandolin, Merlot, Norton, Petit Verdot, Riesling, Sauvignon Blanc, Seyval, Vidal Blanc, Traminette and Zinfandel as well as many fruit wines.

  • Foraging Hike: Learn from the experts at Ashby Gap Adventures how to forage for wild edibles that form the basis of our regional cuisine in the Virginia landscape. Part classroom part hands-on field experience, learn the proper foraging techniques and different recipes to create with your findings. Sample oils, vinegars, sauces, ferments and spices and take home your bounty and use what you learned to create delicious recipes at home!