There is a good italian spot in Winter Garden called Catania and a nice little coffee house I stop at each time I ride through there called Axum.
Once you get past downtown WInter Garden, there is not much at all until you get to Apopka and I personally do not know much about that area.
Word to the wise, do not ride alone close to the Apopka area where the trail ends as it gets a little rough in spots and have heard many a story of people getting pushed off their bikes to have them ripped off.
Besides that the trail is a nice ride and I tend to hit it once a week.