Stamford has stayed fairly safe the past few years with the exception of certain streets on the East Side (Route 1 east of Mill River Park) and West Side (across from McDonalds Exit 9). Crimes in Stamford appears to be as others have said angry drivers and angry drunks leaving the bars on Bedford doing stupid shit, etc.

Nights during Spring, Summer and Fall are relatively safe in the Stamford, Greenwich, Darien area and there's often people out and about downtown, at Cove Island, HarborPoint, etc. Glenbrook at night?? Are you planning to hang at Donut Delight or the 24 hour laundromat? You should be fine but being vigilant about your surroundings at anytime is always a smart call.