48-Hour Itinerary for the Chehalem Mountains

Patricia Green Cellars Vineyard in the Chehalem Mountains

Have you ever experienced the magic of the Chehalem Mountains? Just 20 miles southwest of Portland, it is the perfect weekend visit for Oregon wine connoisseurs. Our world-class wineries, located in the Newberg area of the Willamette Valley, offer memorable tasting experiences accompanied by breathtaking views. To capture the memories, we created the ideal weekend itinerary to some of Oregon’s oldest and most celebrated vineyards conveniently located near one another. 



11:00 a.m. – 1:00 p.m.: Blakeslee Vineyard Estate—Tasting 

2:00 p.m. – 3:30 p.m.: Rain Dance Vineyard—Land Rover Estate Vineyard Tour 

4:00 p.m.: Final Tastings at Chehalem Winery 

5:00 p.m.: Dinner Downtown Newberg & Check-in at the Overnight Guest Houses


10:00 a.m.–11:45 a.m.: Brunch at Jory

12:00 p.m.–1:00 p.m.: REX HILL—Legacy Tour

1:00 p.m.: Head back to where you call home


Blakeslee Vineyard Estate: 11:00 p.m. –  1:00 p.m.


To start your tasting adventure, head to Blakeslee Vineyard Estate, an easy first stop located in Sherwood, Oregon near the Portland Metro area. Blakeslee Estate is known for its award-winning, elegant rich wines and its spectacular views of the Willamette Valley and Mt. Hood. When visiting Blakeslee, you have several sumptuous tasting options, including an indulgent flight of five distinct wines for $30 or making a table reservation in the Piazza for a delicious charcuterie board alongside your wines. We recommend reserving a tasting flight for parties of 2 to 4 people, and a table for larger parties of 6 or more! 


Rain Dance Vineyards: 2:00 p.m. –  3:30 p.m. 


The heavenly Rain Dance Vineyards is the second stop on your journey through the Chehalem Mountains. Rain Dance Vineyards is a family-owned vineyard with specialties and experiences like none other. For the most exhilarating and unique experience in the Willamette Valley, try out the Land Rover Estate Vineyard Tour, and explore two of their most esteemed estate vineyards in a classic 1969 Land Rover. Upon your arrival, you will be greeted with four wines and a hand-crafted cheese charcuterie board, then get whisked away on the estate tour before finishing one final pour back at the tasting room. 


Chehalem Winery: 4:00 p.m. –  10:00 a.m. (Final Tastings & Overnight)


The sun is starting to set, you just had a long day of wonderful tastings and it is time to finish off the night. You are just in luck, Chehalem Winery is known for its overnight guest houses with complimentary tastings for guests. These guest houses accommodate up to 13 guests and include full kitchens, living areas and multiple bedrooms while experiencing the delectable wine and views at the same time. To finish up your first day, we recommend stopping by the tasting room located in downtown Newberg for the last tasting. For dinner, you may choose reservations or take-out from one of the local restaurants. From there, it’s just a quick 10-minute drive up the hill to check in at the Chehalem House. 


Allison Inn & Spa Breakfast at Jory: 10:15 a.m.-11:45 a.m. 


Rise and shine! After checking out of Chehalem Winery at 10:00 am, there is no better way to start off the day than Sunday brunch at the Allison Inn & Spa restaurant Jory. The view from this 5-star hotel is unimaginable, but even more stunning is the food at Jory. Enjoy the perfect morning meal made with local ingredients, by award-winning chefs while looking out into the heart of the Oregon wine country. Sit back and relax and enjoy every bit Jory has to offer!     


REX HILL Winery: 12:00 p.m.-1:00 p.m.


After finishing up brunch at Jory, it is time to finish up your 24 hours of the Chehalem Mountains at one last stop, REX HILL Winery.  Recently renovated, REX HILL is known for its sustainability practices, beauty within the winery, and of course its Legacy Tour, which includes tastings and tours in their historic tasting room tunnels, barrel cellar and production areas. REX HILL is a great last stop before heading back to where you call home; you don’t want to miss it! 


These four wineries are at the heart of the Oregon Wine Country and there is no better place to appreciate a smooth Pinot Noir or the breathtaking views of the Willamette Valley. The Chehalem Mountains encompass over 100 miles spanning three counties and are one of the largest AVAs in the Willamette Valley and one of the nation’s best-kept secrets. Why travel to  Napa Valley when the best of the best is in your own backyard? The Willamette Valley is something you must see to believe to appreciate the beauty of this premier destination truly. Book your trip today because the wineries get booked up quickly!