Neil and Francine Afromsky originally intended to grow Granny Smith apples, but unfortunately, the market for Granny Smiths declined. Consequently, in 1995, the Afromskys purchased a chunk of prime agricultural land (the Westerly Estate) in California's "Happy Valley," located in the extreme southeastern tip of the Santa Ynez Valley. They were the first viniculturists in the Happy Valley, and they turned to viticulturist Jeff Newton to guide them. At first, they planted Bordeaux style varietals; later, they began cultivating Rhône varietals, like Viognier. After the harvest, struck by the quality of the grapes, they decided to make their own wine, and Westerly Vineyards was born.

They collaborated with Kirby Anderson as their winemaker, and began to make their own small batch, carefully controlled limited production wines. Sourcing the grapes from select vineyard blocks, and creating each wine and each blend based on the qualities of the current grape crop. Today, Westerly Vineyards produces Syrah, Merlot, Sauvignon Blanc, Roussane, and Viognier. All of the wines are made in very small, carefully controlled batches. Westerly also uses Viognier grapes to craft their Après, a dessert wine made in the very traditional French Vin de Paille or "straw wine" style, when perfectly ripe grapes on the verge of being over ripe are harvested, then spread out to dry on straw. The resulting dessert wine is sweet, higher in alcohol and rich with flavor. Westerly Vineyard's Après and Reserve wines are made in very limited quantities.

Recently, Robert M. Parker, Jr. gave Westerly Winery's 2003 Syrah "Cote Blonde" a rating of 95+ points. Westerly Vineyard's wines are difficult to find; they have limited distribution in terms of retail, and are rarely seen outside of Connecticut or California.