GPS: 48°41′48″N 122°54′15″W
Eastsound, on the north bend of Orcas Island, is a sort of Nantucket of the West, with a style a bit more Birkenstock than Sperry Top-Sider. As the largest city on the largest island in the archipelago, Eastsound is a good jumping-off point for exploring the San Juans.
The 5,000-acre (2,023-hectare) Moran State Park has over 30 miles (48 kilometers) of hiking trails, just minutes away from Eastsound. Start with Mount Constitution Trail, which climbs 2,400 feet (732 meters) above sea level for 360-degree views of the San Juan Islands, the Cascade Range, the Whistler Mountains, Vancouver, and Victoria (www.parks.wa.gov). Hikers also have the 1,578-acre (639-hectare) Turtleback Mountain Preserve, recently opened after a stunning $18.5 million fundraising effort by San Juan Preservation Trust; take the South Trailhead, off of Deer Harbor Road, to catch a glimpse from the other side of the island to pastoral Crow Valley (www.sjpt.org). Or rent two wheels from Eastsound’s Wildlife Cycles and hit Orcas Island’s well-paved roads. For a longer cycling jaunt, hop on the ferry to explore Lopez or San Juan Islands; the ferry is free for cyclists ($30 for a one-day road-bike rental; www.wildlifecycles.com). Paddlers can explore the Puget Sound’s countless bays and inlets with Shearwater Adventure. On a three-hour guided kayak tour, you could even catch a glimpse of the island’s namesake Orca whale. ($60 per person; www.shearwaterkayaks.com).
Rose’s Bakery Café is a casual eatery housed in Eastsound’s old firehouse. They have a stellar wine selection and use fresh, local ingredients for their homemade bread; the olive-rosemary buns are worth the trip alone (+1 360 376 5805).
Turtleback Farm Inn, a 19th-century farmhouse turned cozy B&B, affords views of Crow Valley, Turtle Mountain, and the surrounding fir and maple forests. Breakfast picks include homemade pastries and granola with fresh-picked wild berries (doubles from $100; www.turtlebackinn.com).