Please note that if you are planning on arriving for Friday night - I would recommend that you make dinner reservations in advance (Actually - for both Friday and Saturday night, plan to do this as restaurants are busy). Check out my restaurant recommendation page for suggestions. Wellington, Bloomfield and Picton all have top notch restaurants, but they all fill up fast!
FOCUS ON THE WEST SIDE OF THE ISLAND (WELLINGTON AND BLOOMFIELD REGION)
If you are able to have two full days in The County, then I would suggest that on the first day - focus on 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. Note that the wineries open at 11:00 am.
Maybe start your day in Bloomfield, poke into a few of the cool stores and then venture over towards Wellington - if Saturday in the summer, there is a great farmer's market. Have lunch at one of their great restaurants that include Midtown Brewery, the Drake Devonshire, East and Main, Enid Grace or if you love food with a super creative Asian twist - you have to check out Idle Wild 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.
You can also grab food at the wineries in some cases too. Also - in addition to having some of the cutest shops in PEC, Bloomfield also has some amazing restaurants including Bloomfield Public House, Flame + Smith, Saylor House, and The Agrarian.
FOCUS ON THE EAST SIDE (PICTON, LAKE-ON-THE-MOUNTAIN AND WAUPOOS REGION)
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. Maybe consider having a charcuterie-style lunch at The Miller House - it really has the most breath-taking view in PEC, the food is delicious and the service is outstanding. 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. 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! It has been said that the east side of the island is the most scenic, and I agree :)
THEN START PLANNING YOUR NEXT GETAWAY HERE, BECAUSE YOU CAN'T POSSIBLY DO IT ALL IN JUST ONE WEEKEND!