"A 10-minute drive from downtown Ashland, Weisinger Family Winery was the first winery in the Rogue Valley when it opened in 1988. Its casual two-story, dog-friendly deck with sofas and expansive views of the Siskiyou Mountains is a delightful place to taste wine, which hails from its own vineyard or within five miles. A flight of six is $18." - Sharon McDonnell