Unless you are accompanying a child who is trick-or-treating, in some Virginia localities if you are over the age of 12, you are in violation of the law if you trick-or-treat! This could mean a fine or jail time.
While I cannot find any local ordinances for Winchester/Frederick County/Clarke County making trick-or-treat a violation of the law, local jurisdictions do set safety guidelines for trick-or-treat. For example, the Town of Stephens City has Halloween set from 5:30-8:30. The City of Winchester’s trick-or-treat is from dusk until 8:00. The Town of Berryville has set its Halloween hours from 6:00-8:30.
Virginia prohibits the use of a mask, hood, or other device by anyone over 16 years of age, in any public place, or in any private property without obtaining consent to do so from the owner or tenant. There are exceptions, which include wearing a traditional holiday costume, but because Halloween is on Wednesday this year, wearing a mask on the streets while on the way to a party or just wearing one in the streets in general this coming weekend will be a violation of the law, carrying a penalty of 1-5 years and a fine of up to $2500.