If you are rich, white, old, retired, and married, this is the place for you. If you are a minority who accepts white supremacy and don't mind being patronized, ostracized, and discriminated against, this place is for you. This is the south and racism is alive and well here! If you are familiar with the Civil War, slavery, discrimination, white supremacy, and old-time money, Winchester has a few descendants of that era. Many of the people will be nice, smile and talk with you, but do not be fooled into thinking they think you are their equal. There is a caste system here and people seem to know and accept their level on the racial and class ladder. This is a small town where everyone seems to know someone or know someone that person knows. Everyone is connected in some way or another. Be careful if you talk, what you say, who you say it to, and how loudly you say it. The town is full of gossips who enjoy spreading other people's business. It is not always slander as a lot of the gossip is actually true. If you love gossiping or being gossiped about, this place is for you!If you have a problem with alcohol and drugs, this place is for you. It is filled with substance abusers. Lots of DUI arrests, heroin overdoses, and alcoholics here. If you smoke marijuana, avoid this place! If you drink alcohol and are caught walking, driving, and bicycling afterward, YOU WILL BE ARRESTED! The State of Virginia has an alcohol program that strongly ENFORCES arrests! You will be forced to pay thousands of dollars in court fines, legal fees, counseling and education in addition to spending hours, days, weeks, or months in jail. Again, if you do not have an arrest record and you love to drink or do drugs, AVOID Winchester!The dichotomy of the population is financially secure to rich and financially insecure and poor. The rich feed off of the poor. The poor complain, whine and loathe the upper class. Lawyers, therapists, judges, law enforcement, professors, doctors, and businessmen (especially restaurant/bar owners, and mental health or recovery facilities) all get rich off of the lower class. The good news is that the upper class feed their sense of supremacy by donating lots of money and goods to an abundance of programs that serve the poor with food, clothing, shelter, and medical care. You can get free food from at least 10 to 20 different sources, so you would never starve here. There is no real public transportation like you would find in a large city. There is some little trolley van that runs certain hours during weekdays. There are two, maybe three cab companies, but you might see a falling star before you actually see a cab. Sometimes they will get to you within 10 minutes. Other times, you can walk and get to your destination before the taxi ever arrives. If you live in an apartment or rental, BEWARE! The management company will enter your residence with their key without your approval, while you are away at work. They will also enter when you are home sleeping, bathing or doing or private things that a person does in the comfort of their own home. They will not apologize for this disrespectful intrusiveness. They claim it is all in the name of inspecting and maintaining their property. If you do not like strangers entering your place, buy your own home, change your locks (this is actually illegal), or AVOID moving to the Winchester area. Properties owned by the Aikens family are the worst!Rubbermaid and a few small plants employ a lot of blue collar workers. Shenandoah University brings in a diverse population of students who cannot wait to leave after graduation. Winchester Valley Health has expanded and employs lots of medical professionals and staff. The university has plays and musical entertainment. If you have school age children, avoid this place! The schools are filled with drugs and alcohol abusing students from dysfunctional homes. This is a couples town, so single people should move elsewhere if they hope to marry. If you love to drink liquor, beer, and wine, this town is definitely for you! If you enjoy dining out or spending time in nice hotels, there are plenty of restaurants and hotels here. There are two Targets, three Wal-Marts, several grocery stores, and strip malls scattered within 5 to 20 minutes of each other.