The second oldest town in Washington, the “Port of Sea Captains” was founded and laid out in 1852 by Capt. Thomas Coupe, the first man to sail through Deception Pass. The protected harbor at Penn Cove was a perfect site for the village that became Coupeville, and timber from Whidbey Island was shipped from here to San Francisco to feed the building boom created by the gold rush.

Today, modern businesses operate from Victorian-era buildings amidst the nation’s largest historical preservation district. Downtown has an immaculate cluster of false-fronted shops and restaurants right on the harbor and a long wharf that was once used to ship local produce and logs to the mainland. This is a cat-friendly town; perhaps half the downtown businesses have one inside.

Getting to Coupeville

Island Transit, (360/678-7771, or 800/240-8747, www.islandtransit.org) has free bus service Mon.–Sat. throughout Whidbey. Whidbey Scenic Flights (360/678-8384) offers airplane flights over the island.