Curling Vine Winery —formerly Stone Hill Winery is the oldest in town and they do a very nice tour and tasting. The store has lots of interesting things and it is a fun free stop.
Mount Pleasant Winery is newer and seems nice. It may have changed, but their tastings were not free when we visited.
St James Winery has long been a southern MO favorite and FINALLY has opened a wonderful winery and restaurant in Branson. St. James Velvet Red is my personal favorite. The tasting experience here is exceptional! The staff is very knowledgeable and entertaining! I highly recommend this one. The restaurant is good and now has a patio as well. Super nice place to visit!
There is Wine garden off Hwy 265 that we have not tried yet but hope to soon.