Police in Winchester are searching for the suspects who used a high-powered slingshot to smash windows and doors at local businesses and homes.
"It just really hurts," said Robert Patton-Spruill.
He's spent the last two years and his life savings to renovate and restore a historic Winchester building into a distillery.
"Some of these windows are 120 years old, so yeah, there's a little bit of history here," Patton-Spruill said.
Overnight Saturday vandals struck and ruined what he worked so hard to preserve.
"It's just profoundly disappointing," Patton-Spruill said.
Just a few doors down at the Main Street Mini-Mart.
A shattered front door forced Manager Danny Soni to shut down for two days.
"It's just really sad," said customer Kristi Johnson.
The closure cost the store about $10,000 in business. But still, Soni says he's most worried about his customers.
"Because we have a high traffic area over here," he said. "Anybody can get shot, if they can break the windows, they can break anything."
Winchester Police believe the suspects struck with a high powered sling shot, marbles, and metal pellets.
"You get hit in the temple with one of these things, it's deadly," said Chief Gary Phillips.
Chief Phillips says the vandals hit five different spots around town, including an apartment. Thankfully, no one was home.
"Oh my God, what if we were sitting there in the living room and all of a sudden something comes flying through out of nowhere," Johnsons said. "It's scary."
"It's dangerous, it's a serious crime," Chief Phillips said. "God forbid somebody got injured by one of these things, it could be negligent homicide."
And while nobody was physically hurt, business owners say the thousands of dollars worth of damage is painful enough.
"From an emotional standpoint we all got hit," Patton-Spruill said. "We are a down-on-its-luck mill town trying to pull ourselves up by the bootstraps and the last thing we can have going on here is wanton damage to history...that's all we got is history."
Police say they're trying to get ahold of surveillance video from around town.
The suspects could be facing felony charges.