Exploring Oregon’s Wine Country: A Journey of Connection, Flavor, and Unforgettable Moments

This August, we embarked on a truly special journey through Oregon’s wine country as part of our Picnic Wine Adventures. For me, this trip was more than just a chance to explore incredible wines—it was a homecoming, an opportunity to share the place where I was born and raised with a group of wonderful people. Our journey was filled with laughter, learning, and experiences that brought us closer together, all set against the backdrop of Oregon’s stunning landscapes.

Day 1: Arrival in Portland

Our adventure began with everyone arriving in Portland from different corners of the country—some by plane from Chicago and San Francisco, others by car from Seattle. I was already in town for my son’s wedding, so my mom dropped me off at our hotel. Thanks to the wonderful service at the Dossier Hotel, everyone was able to check in early and take some time to explore Portland on their own. We gathered at Bar Alder for a welcome cocktail before heading out to a delicious Peruvian dinner at Andina.

Day 2: Into the Heart of Willamette Valley

After enjoying breakfast, we made our way to our beautiful Wine Country Home in Dayton, Oregon. Along the way, we stopped at Carlton Winemakers Studio, a co-op that features wines from over 20 different winemakers. We were lucky enough to meet Peter Sturn, the winemaker at Eila Wines, who poured us a delightful Chardonnay and Pinot Noir—definitely a highlight of the stop. Peter, originally from Chicago, even visited us at Picnic recently, and we’re excited to bring some of his wines into our collection.

Later, we checked into our house, a stunning and spacious home with a giant porch, hammocks, and plenty of room to relax. The day’s highlight was our visit to Brooks Winery, where we enjoyed a tour, tasting, and dinner. This was a particularly special moment as my childhood friend Johanna Copeland, along with her partner Jay, her mom Phyllis, and my mom, joined us for the experience. Brooks has always been a favorite, and this visit was no exception—the gardens were beautiful, the food was fresh and delicious, and the wine pairings were spot on. We had lively conversations, shared laughs, and left feeling incredibly satisfied. The evening ended with us back at the house, playing Cards Against Humanity and sipping wine late into the night.

Day 3: Highlights and New Discoveries

The third day of our trip started with a big group breakfast at the house, setting the stage for what may have been the best day of the journey. Our first stop was Lemelson Vineyards, where we were joined by our good friend and wine club member, Gail, who happened to be in Oregon as part of a West Coast road trip. Lemelson’s wines were spectacular and voted as the group’s favorite. The view from the vineyard was breathtaking, and the facility itself is a marvel, built into the mountain with exceptional attention to detail.

Afterward, we visited Jessica Mozeico of Et Fille at her home in the hills. This was perhaps the most intimate experience of the trip. Jessica welcomed us with open arms, introduced us to her dog Coco, and took us on a walk through her three acres of vines, which are perfectly situated for the changing climate. We shared personal stories, bonded over shared experiences, and enjoyed her beautiful wines paired with homemade buckwheat pancakes, crème fraîche, caviar, and charcuterie. It was a deeply personal and memorable experience that left a lasting impression on all of us.

That evening, we decided to forgo dinner out and instead cooked at the house. Jim grilled burgers, I made a salad, and everyone contributed snacks as we enjoyed our wine purchases from the day. We spent the night on the back patio, sharing stories and soaking in the peaceful surroundings.

Day 4: Immersing in Oregon’s Wine Culture

We began the day with breakfast at the house before heading to Left Coast Estates. Left Coast is a 490-acre vineyard, winery, and working farm with a strong focus on ecological stewardship. We had a wonderful tour around the farm in their flatbed truck, learning about their low-impact viticulture and the efforts they’ve made to conserve and restore 100 acres of Oregon White Oak savanna. It was a beautiful and educational experience that underscored the importance of sustainability in winemaking. On our way back to Portland, we made a stop at the Portland Japanese Garden, one of the best outside of Japan. It was an oasis of peace just outside the city, where all the sounds seemed to vanish into the lush landscape. Walking around the garden was a great change of pace and a perfect way to end the day before heading to our final stop, The Jupiter Next in Portland.

Day 5: Reflections and Farewell

Our final day was a mix of exploring a bit more of Oregon and reflecting on the incredible journey we had shared. The emotional farewell was bittersweet, as we were all sad to see the trip come to an end but grateful for the memories we had created together.

The Magic of Oregon: Why This Trip Was Special

Oregon’s wine country is a place of magic—its rolling hills, lush vineyards, and passionate winemakers create an atmosphere that’s both welcoming and awe-inspiring. There’s something special about the winemakers of Oregon that sets them apart from other wine regions. They are welcoming and genuinely bring you into their world. There’s no pretense or pretentiousness—you are treated like family. This sense of connection made the trip truly unforgettable.

The wines we tasted were elegant and complex, each bottle telling a story of the land and the people who tend it. From the intimate moments at Et Fille to the lively discussions at Brooks, every part of this trip was about connection—connecting with each other, with the land, and with the wines we love.

Looking Ahead: Join Us Next Year

This trip was just the beginning. We’re already planning our next adventure, and we’d love for you to join us. Whether you’re a seasoned wine lover or just starting your journey, there’s something truly special about exploring the world through wine. Keep an eye out for details on our next trip, and let’s continue this incredible journey together.