Go Here: Abandoned Renaissance Faire in Fredericksburg, VA
I went to college in Fredericksburg -- a small, seemingly fictional city halfway between DC and Richmond. After growing up in New York it was a radical change, and I spent most of my (five, oops) college years exploring the strangest parts of Virginia. This place remains one of my favorite discoveries of all time.
The ruins of the VA Renaissance Faire sit just outside of the city on Route 3, on plot of land with a long history, like much of Fredericksburg. The property was once owned by George Washington's mother, and is located in an area appropriately named 'Sherwood Forest.' Renaissance Entertainment Corp bought the land for $3 million, and the faire operated from 1996 - 1999, when it tanked due to lack of profits. It has sat vacant and hidden in the woods ever since.
The grounds are immense, and most of the large, elaborate buildings still stand, though they are beginning to be overtaken by nature. There is a large ship structure with a moat, towers and turrets for climbing, the remains of a jousting arena, a bar with kegs built into the walls, and plenty evidence of the spot's long history of squatters, graffiti artists and paintball players.
If you're planning on going, you'll need long pants and socks, sturdy shoes and plenty of bug spray -- the area is tick paradise. If you visit during hunting season, wear orange, and stay alert. Summer is by far the best time to visit, and learn from my mistake: it is not safe to go at night. Most importantly, always remember to be respectful, safe and discreet when exploring abandoned areas -- Don't ruin it for the rest of us! Happy exploring!