Sheila Johnson's 340-acre Middleburg estate — Forbes 5-star, AAA 5-Diamond. Middleburg is Virginia hunt country (foxhunts, Gold Cup steeplechase, vineyards). Bachelor angle: 22-stall stable + 9 paddocks for trail rides, sporting clays at the on-site range, wine tasting at Boxwood and Greenhill (within 5 miles). Spa day for the recovery, dinner at Harrimans (the resort's signature; chef-driven Virginia cuisine). Day three: Salamander Spirits whiskey tasting (Sheila Johnson's distillery program), the historic Red Fox Inn for a final pint (1728, oldest continuously operating tavern in America). Dulles (IAD) is 45 minutes east.
Five quick questions, then we build the full itinerary — lodging, daily schedule, dining, bars, the group-chat message — and drop you into a Trip Room you can share with the crew.