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Question as in the title.

I commonly use the phrase "out and about in town" in speech.

I'm not sure if my usage is correct because of the "night on the town" phrase.

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Both usages are correct.

The usual phrase for being in the city is "in town". This just refers to your physical presence there, without much implication about what you might be doing there - one would normally assume that you were shopping, visiting people, or even just staying at home (if you happen to live there).

The phrase "on the town" has a slightly different meaning - there's no one specific connotation, but one would understand that you were visiting restaurants/pubs/bars, socialising, and very likely drinking as well. I doubt that there is any direct etymological link, but to me the use of "on" is similar to usages such as "on the prowl", "on the warpath", "on the booze", "on the pull" and so on.

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  • Yeah, I'm referring specifically to the night out partying/boozing et al. So we would not use "night out in town" for that?
    – JoseK
    Apr 8, 2011 at 10:41
  • @JoseK: There's nothing wrong with saying that - the "night out" usually implies some sort of socialising, so there's no need to have it twice - but the "in town" bit just specifies a location. Both phrases (in/on) mean roughly the same thing, but on the town has a stronger connotation of partying/boozing, whereas in town sounds slightly "better behaved" :)
    – psmears
    Apr 8, 2011 at 12:12
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"Night on the tiles" is a phrase which draws imagery of the wild nocturnal activities of cats as they have fun over the rooftops. As metaphorical expression are used and adapted over time they adopt new meaning and connotation, so what was a "Night on the tiles" has evolved to become a "Night on the Town".

Simplistically, the meaning and intention of the phrase "Night on the town" is easier to understand than the phrase "Night on the tiles". It is implicit in the former that you will be going to town at night, in the later you may have to explain what exactly you mean by tiles.

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    Interesting! So you are sure night on the town evolved from night on the tiles? It would be great if you had some kind of reference too.
    – Cerberus - Reinstate Monica
    Apr 8, 2011 at 21:44
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The phrase 'night on the town' is similar to 'drinks on the house'. Though you are having drinks 'in' the house, the common usage is 'on the house' to portray that 'house' is playing host. In former case, the 'town' is playing host, sort of!

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    "drinks on the house" implies who is paying for them - not just the hosting location. you also say "drinks are on me" when you're paying but not neccesarily hosting.
    – JoseK
    Apr 8, 2011 at 11:27
  • Doesn't 'hosting' imply 'paying'? How can one be a 'host' and not 'pay'?
    – amit
    Apr 13, 2011 at 12:08
  • @amit When "drinks are on me", that means, I'm paying. (i.e. they are on my bill) A bartender might then say "Drinks are on him", even though he represents the house (an example when the guy paying isn't the host). Similarly, the bartender might say "Drinks are on the house", which means the house is paying, and the house in this case is the host. If I'm hosting a party at my house, that does imply that I'm the one paying for the consumables, but it's also possible that I'm hosting, but someone else is bringing the food / drinks.
    – McKay
    Jun 6, 2018 at 17:59

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