Is there a good reason I see VARCHAR(255) used so often (as opposed to another length)?

Question

255 is used because it's the largest number of characters that can be counted with an 8-bit number. It maximizes the use of the 8-bit count, without frivolously requiring another whole byte to count the characters above 255.

When used this way, VarChar only uses the number of bytes + 1 to store your text, so you might as well set it to 255, unless you want a hard limit (like 50) on the number of characters in the field.

Historically, 255 characters has often been the maximum length of a VARCHAR in some DBMSes, and it sometimes still winds up being the effective maximum if you want to use UTF-8 and have the column indexed (because of index length limitations).

Probably because both SQL Server and Sybase (to name two I am familiar with) used to have a 255 character maximum in the number of characters in a VARCHAR column. For SQL Server, this changed in version 7 in 1996/1997 or so... but old habits sometimes die hard.

I'm going to answer the literal question: no, there isn't a good reason you see VARCHAR(255) used so often (there are indeed reasons, as discussed in the other answers, just not good ones). You won't find many examples of projects that have failed catastrophically because the architect chose VARCHAR(300) instead of VARCHAR(255). This would be an issue of near-total insignificance even if you were talking about CHAR instead of VARCHAR.