Is it better to not mention anything until it is brought up, or do you mention it right away so both parties understand what each other is looking for? First date, or not at all until asked?

( Background )I live in a ski town that is just big enough to date around but the social circle is still pretty small and you see the same people often or everyone is friends of friends with someone you know. Because of this it could be easy to get a bad reputation if your not careful.