A man was caught trespassing on a property on Birmingham Street in Halifax in September. Google Streetview

A Dartmouth, N.S., man charged with trespassing at night has a long history of stalking and voyeurism.

Barry Sinclair, 49, has been behind bars since September awaiting a bail hearing on a charge of trespassing at night in Halifax's south end.

Halifax police say they observed a man acting suspiciously in the area of Birmingham Street at 4:15 a.m. on Sept. 17. They say Sinclair was on a deck at the back of the home near a window.

Officers tried to arrest the man, but he was combative, police said. The man was taken to hospital with minor injuries.

Parole board documents obtained Friday by CBC News show that in October 1999, Sinclair was denied parole for a four-year federal sentence for breaking and entering.

The parole board noted his "convictions of sexual assault, indecent exposure, and trespassing at night. Many of the property offences are related voyeuristic behaviour, and with such an offence cycle, the intent of the current conviction becomes particularly alarming."

Stalking female volunteer at half-way house

Sinclair was released in 2001 after serving two-thirds of his sentence. His parole was revoked because he was identified as "stalking a female volunteer student worker at Railton House," the board says. Railton House is a half-way house run by the Salvation Army in Dartmouth.

It added, "your risk of engaging in future sexual assaults should not be underestimated."

He was released again in 2002, but within days police had spotted him entering a number of female washrooms in office buildings.

In September 2005, he was caught trespassing at night and given a six-month sentence.

Parole board files are kept for ten years from the end of a sentence and then destroyed.

Sinclair is in jail now charged with trespassing and drug possession. He can apply for bail Oct. 17.