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[ynmaker]

I am in the process of starting a winery using my mothers maiden name. The label I hope to use is an old 1920's Fruit label that my Great Grandfather used to label his Pears.  
I have since found a registered Trademark for a restaurant in another state that is using a modified version of this exact label as the logo for his BBQ restaurant. The modification is simply the addition of "Smokehouse BBQ" Where my Great Grandfathers name and the name of the fruit was.

My questions are,
1) How can someone trademark a logo that was created by my family in the 1920's?
2) Is it still possible for me to use the original label for my wine?

[clarklawyer]

My questions are,
1) How can someone trademark a logo that was created by my family in the 1920's?

Simply creating a logo does not provide any trademark rights.  Trademark rights come from using a mark in commerce to identify goods and services.   If the trademark is not federally registered, then the extent of the trademark would be the geographic area in which the mark is used.

So one theory is that the restaurant was able to use your trademark outside of your geographic area, and was able to register the trademark.   In that case you would be the senior user within your geographic area, but not outside of that area.

Another possiblity is that sometime between the 1920s and now, your logo stopped being a viable mark because you were not applying it to goods in commerce.   In that case a federally registered mark would be the senior mark even within your geographic area.

The senior (in time) mark holder wins in a contest between confusingly similar marks.

2) Is it still possible for me to use the original label for my wine?

There's no easy answer to that question.   If you are the junior mark holder, and your mark is confusingly similar to the restaurant mark, then your use would be infringing.  

For one thing, it's not possible to tell from your description just how similar the restaurant mark is to the mark you want to use.  

For example:

Does the text dominate relatively inobtrusive artwork, or does the artwork of the logo dominate?   Exactly what is shown in the artwork?   Is it something that would be otherwise generic or descriptive is used on fruit?   What dissimilar elements appear in the two logos.

I'm not looking for you to provide answers or more info.  The questions are just to indicate why I'm not giving you a more specific answer.

[JSonnabend]

Worse still for you, I'm afraid, is the existence of a recent TTAB precedential opinion regarding -- and I'm not making this up -- the likelihood of confusion between marks for wine and marks for restaurant services.  The decision goes a long way to saying that the two goods/services are closely related, although it doesn't go so far as to create any purported per se rule.

Also, surnames are not always registerable without a showing of secondary meaning.  Much depends on the amorphous inquiry as to whether the mark acts "primarily merely as a surname."

- Jeff