I also grew up in Niagara and DH and I regularily do the "Wine Route"! It is so much fun... we are actually thinking of doing it next weekend. I agree with those saying that it is more fun to go from winery to winery and try different things at each. It is better to go when there is an event on, for sure. If you want to go right away, fall is beautiful. However, in January, there is also the
Icewine Festival. Lots of fun!
As for restaurants, we haven't done any fine dining out for a while but all the suggestions above are very good!
One thing (and winery!) that I highly recommend is the tasting plate though, at
Jackson Triggs. It is a must!
In addition to Jackson Triggs, try
Inniskillin (both are in Niagara on the Lake), and
Vineland Estates (this one is between Hamilton and St Catharines...) but is a gorgeous place to visit, well worth the drive. If you like fine foods,
Stoney Ridge is close by and has great cheeses.
Last of all, also in Niagara on the Lake, everyone should visit
Kurtz Orchards. It has an amazing selection of goodies, not wine, but enjoyable none the less!
Have fun!!!!!!!!!!!