When Vancouver sailed through Puget Sound in 1792, he didn't realize that Bainbridge Island was an island. Then in 1841 Charles N. Wilkes found Agate Pass, the waterway separating the island from the Kitsap Peninsula. Wilkes named the island for Capt. William Bainbridge, a Naval hero from the USS Constitution. Within 15 years of its charting, Bainbridge Island was home to one of Puget Sound’s greatest lumber mills, and soon thereafter its ports were world renowned. Port Blakely had the biggest sawmill in the world, employing more than 1,000 men, and the shipyard there built the largest sternwheeler at that time in the Pacific Northwest, the Julia.

Today the four- by 12-mile island is almost entirely privately owned by politicians, doctors, artists, many stockbrokers, a few fishermen, and a lot of ordinary folks, including 70 percent who commute by ferry to Seattle-area jobs. Although the entire island is officially incorporated, there is only one real town: Winslow, located along Eagle Harbor where the ferry docks. Winslow is a genuine—albeit gentrified—town with Volvos crawling the streets, yachts in the marina, and classical music in the cafés. Several other small settlements are scattered around Bainbridge, including Lynwood Center and Island Center.

If you're arriving by ferry from Seattle, you'll find Winslow an easy place to explore by foot. Start on the shoreline footpath that heads west from the ferry to Eagle Harbor Waterfront Park, a fine place for a sunny-day picnic. If you're arriving by car, parking can be a real problem on weekends, and no on-street overnight parking is allowed.