Willamette Valley Wine Country & Oregon City

A 700-acre estate on the Dundee Hills' eastern slope, established in 1989 and now producing some of Oregon's most recognized Pinot Noirs — the Evenstad Reserve and the Grace Vineyard are the flagship expressions of the estate's volcanic Jory soil. The hilltop visitor center has the finest architecture of any Willamette Valley winery and a terrace view that encompasses the full valley floor.

A Newberg winery in a converted hazelnut-drying barn that was Oregon's most photographed tasting room before the Dundee Hills boom — the estate dates to 1982 and produces Pinot Noir from the original Red Hills plantings. The 2-acre garden surrounding the barn is at its peak in June.

David and Ginny Adelsheim planted their first vines in 1971, established among the early pioneers of Willamette Valley pinot noir alongside the handful of families who defined the appellation in its founding decade. The Chehalem Mountains estate produces one of the appellation's finest Pinot Gris alongside its Pinot Noir; the tasting room's covered porch overlooks the estate vineyard.

The flagship restaurant of the Willamette Valley's finest wine country inn — the menu is built around Oregon Coast seafood, Willamette Valley produce, and the surrounding farms, paired with an exclusively Oregon wine list. The dining room looks directly over the estate vineyard; the kitchen's Pinot Noir reduction is the region's most concentrated single-table argument for why this wine country belongs in Burgundy's conversation.

On May 2, 1843, American settlers voted to establish a provisional government at this meadow on the Willamette River — the 52–50 vote that created Oregon Territory and laid the groundwork for US annexation of the Pacific Northwest. The site preserves the original townsite of Champoeg (abandoned after an 1861 flood) and the meadow where the vote occurred, with a visitor center documenting the French-Canadian and American settler communities that made the decision.

The 1845 Federal-style home of John McLoughlin — chief factor of the Hudson's Bay Company at Fort Vancouver and the man who provisioned starving Oregon Trail emigrants from his personal stores against company orders, an act of generosity that cost him his job and helped secure American settlement of the Willamette Valley. The house is preserved with original McLoughlin family furnishings; the story of his loyalties between the British company, American settlers, and his mixed-race Métis family is the central human drama of Oregon's founding era.

The only outdoor vertical street elevator in the United States, operating since 1915 to connect Oregon City's upper bluff with its lower commercial district — a 130-foot ride that replaces what would otherwise be a 25-story stair climb. The upper bluff contains the McLoughlin House, home of the 'Father of Oregon' John McLoughlin, who served as chief factor of the Hudson's Bay Company at Fort Vancouver and helped establish the Willamette Valley settlements.

Oregon City's best dining room in a historic building above the Willamette Falls — the kitchen produces Willamette Valley seasonal cooking with a wine list anchored by the surrounding wine country. The falls below the restaurant drop 42 feet over a basalt ledge; the water power here drove Oregon's first paper mill, first flour mill, and first textile mill.