Loi Kroh Road

We cannot not mention it: Chiang Mai also has its own small Red Light District. Just one street long, Loi Kroh Road, ending in a semi-open-air area with several dozen bars, each with a pool table, and behind that one of Chiang Mai’s boxing stadiums.
Not really "safe" for a man alone — sometimes you literally get pulled inside one of the bars by the arm. Or at least you’ll hear “Hey Mister, Hey Handsome, where are you going” quite often. But if you’re curious about Thailand’s reputation, you can also just quietly have a beer there and watch the world slowly pass by...

A small word of caution: Loi Kroh Road is 'okay', but elsewhere in Chiang Mai there are certain so-called 'karaoke bars' where you might go inside with a girl, order a drink, and before you know it, your bill has run up into thousands of Baht for just 1 or 2 drinks...