If you are able to have two full days in The County, then I would suggest that on the first day - you focus on the area in the map below - the western part of the island. A lot of great wineries are concentrated in the Wellington/Hillier area, and there are some fun stores in the Bloomfield area. Maybe start your day in Bloomfield, poke into a few of the cool stores and then venture over towards Wellington. Have lunch at one of their great restaurants (or at Norman Hardie's Winery for deelish pizza if on the weekend) and then tour the vineyards. There ARE limo companies that you can hire to do the driving for you if you are interested in visiting a lot of wineries and not having a designated driver.
The second day - you might want to start in the city of PIcton and check out the shops. Maybe even start off your day with a coffee from Miss Lily's Cafe or The Bean Counter. Then - head over to the Glenora Ferry and take a short 10 minute trip across the water (Aldophus Reach) and visit the 33 Vines Winery! I LOVE the ferry ride, it is short but beautiful (if staying for more than a few days - continue on that highway to Kingston for a fun day trip). After that - head back to the ferry, hop on back to the county and then head up to Lake-on-the-Mountain and take in the view and history. There, you can have lunch or perhaps a coffee/drink and something light to eat. Then follow the road around to Waupoos and check out the County Cider Company (GREAT cider, good food too). Don't forget to continue onto Fifth Town Cheese - wonderful locally produced goat and cow cheeses as well as incredible imported Italian products. The map below outlines what we love most along this route. From Waupoos, I would head towards Black River and visit Vickies Veggies and then stop and pick up some Black River Cheddar Cheese and maybe grab an ice cream cone! If you are ambitious, you can probably do all of this. If you want to take it easy - pick and choose your stops along the way, but try not to miss Lake-on-the-Mountain, Fifth Town Cheese, The County Cider Company, Black River Cheese and Vicki's Veggies!