Driving through the long stretches of pastures and fields south and west of Vineyard Haven , you can quickly forget that you are on an island. The western side of the island is more “real” than the glitzy towns to the east, with sleepy corner stores and cattle barns.
In the center of the Vineyard is, fittingly, Chicama Vineyards (Stoney Hill Rd., off State Rd., West Tisbury, 508/693-0309), the first winery in Massachusetts , which offers tours and samples of its wines, mustards, and vinegars.
Nowhere is more of a throwback to the early days of the island than the pristinely crumbling fishing village of Menemsha, a smattering of grey-shingled shacks and beach houses beside a small harbor of fishing trawlers and lobster boats.
On the far western end of the island, Aquinnah is home to both a Wampanoag community and the breathtaking clay cliffs of Gay Head, which glow with orange and purple hues in the afternoon sun.