Road Trip Season is here, and I’ve been sharing itinerary ideas to help get you started. So far we’ve hit the southeast with an America’s Best Barbecue pilgrimage and the northeast with a New England’s Literary Treasures itinerary. Up next: The northwest—specifically, Oregon.

On one side of Portland lie the Willamette Valley’s vineyards that produce some of the country’s best pinot noirs. It’s a greener, more rustic version of Napa; the vineyards are less manicured, the mood more relaxed. On the other side of the city lie dramatic gorges and waterfalls where the Columbia River cuts through the Cascade Mountains. You could spend a week oohing and aahing your way along the back roads in this part of the country. Heck, you could even take a few summer ski runs down a volcano, on the only slopes in the U.S. that are open year-round. If you’ve only got a weekend, though, you can base yourself in Portland and still get a flavorful taste of the area. Here’s how:

Day 1

From Portland (1), head southwest on 99W into the Willamette Valley, stopping at any of the many picturesque wineries whose vistas and tasting rooms will beckon. Ponzi Vineyards (2) is a must—you can taste leading pinots and pick up some Ponzi Reserve for a picnic lunch later—as is Beaux Freres (3) (email ahead to make an appointment for a tour and tasting). At lunchtime, grab some local provisions [or splurge on the “Wine Touring Picnic” from Black Walnut Inn & Vineyard (4)] and head to Erath Vineyards (5) for your picnic with sweeping views of the Jory Hills of Dundee. Don’t miss Domaine Drouhin (6) and Archery Summit (7) en route to McMinnville, a hub of excellent shops and restaurants. Choose Nick’s Italian Café (8), an Oregon wine country institution, where you can shoot pool with local winemakers and taste any wines you may have missed in the vineyards. Drive—carefully—back to Portland.

Day 2

Next day, head east along the historic Columbia River Gorge Scenic Highway (1). Make quick pit stops at the Portland Women’s Forum State Scenic Viewpoint (2) in Corbett and at Vista House (3) at Crown Point for the stunning views of towering cliffs and waterfalls. Consider a morning hike to the top of Multnomah Falls (4), a 542-foot plume that plummets into a forest grotto, or along the Eagle Creek Trail to Metlako Falls and Punch Bowl Falls (5). At the town of Hood River, if it’s a clear day, make the 25-mile detour to Lost Lake (6) for its spectacular views of Mount Hood, the greatest of the Oregon Cascades. Continue south on Route 35 through the fruit orchards of the Hood River Valley, stopping to pick your own apples, cherries, peaches, and tomatoes. Where Route 35 meets Highway 26, make a quick detour to Timberline Lodge (7), a National Historic Landmark that you might recognize from the movie “The Shining.” (If you had more time, you could squeeze in the aforementioned summer skiing.) Back on 26, wend your way west, through forest and Cascades, back to Portland.

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