Music and light filtered through the trees as I walked to the next show. Glowing sculptures floated among the leaves overhead. The flow of people guided me forward. I’d already been to seven concerts that day, but Haley Heynderickx is an Oregon native, and I knew I needed to see her. I walked out of the tunnel of trees into a ferny glade. At the center, a stage of woven branches cradled the artist as she began to sing. I was at Pickathon and I never wanted to leave.
Once a year, 80 acres of farmland in Happy Valley transform into one of Oregon’s premier music festivals. Pickathon has been running since 1999 and is a destination in its own right. Thousands of fans and artists flock to nine stages scattered across Pendarvis Farm, about 15 miles southeast of Portland. Last year I wanted to make the most of my week off. So, to prepare for four days of music, I escaped to some of Oregon’s most peaceful destinations. Here’s how to plan your perfect Pickathon road trip — experiencing Oregon’s scenic beauty and serene wellness destinations — before plunging into some of the state’s top music, food and community.
Scenic Hikes, Cozy Lodging and Starry Skies at Crater Lake
For the full road trip experience, you can kick things off by flying into the Rogue Valley International Airport in Medford, which puts you just over an hour from Crater Lake National Park. Driving Northeast from Medford, I followed clear, calm water up the Rogue River Valley. I got to the Mill Creek Falls Trail early and spent the morning taking in the scenery, including neighboring Barr Creek Falls. I got my fill of waterfalls before heading north to Beckie’s Café for my fill of homemade pie. Beckie’s has been around for 100 years and their historic homestyle cooking was a welcome addition after my drive.
Wiping blackberries from my mouth, I got back on the road. Forty minutes later, I was standing in front of Crater Lake Lodge. This historic lodge offers cozy rooms, fine dining and some of the best views of Oregon’s only national park. I stowed my car and hiked the Discovery Trail until I got hungry (after my lunch, it took a while). When I was ready and the sun was a little lower, I headed back.
I returned to the Lodge’s Dining Room, which offered an elevated culinary experience and views of the lake that were even higher. I started my evening with a 12oz Ribeye and a view of the sunset from their expansive stone patio. Thanks to Southern Oregon’s protected dark skies, my night continued past daylight. As the sun dipped behind the lake rim, my eyes adjusted and the evening’s performance blinked onto stage. Millions of stars spun above me, and I stayed out for as long as I could. The lake still reflected the glow of the Milky Way as I walked to my room.
After staying up to see the stars, I started my morning late. Revived by a breakfast sandwich at Annie Creek Restaurant, I hiked up the Garfield Peak Trail. The top of the trail offered panoramic views of America’s deepest lake. Walking back, I was surprised to find that one of my favorite views was the lodge nestled into the hillside. It stayed with me in the rearview as I packed up and headed out.
Oregon’s Scenic Byways, Eco-Friendly Lodging and Hot Springs
With some snacks from the Rim Village Café, I headed north to Redmond. I knew I had a long drive ahead of me. Leaning into it, I decided to leave Highway 97 and take the Cascade Lakes National Scenic Byway. It added two hours of driving time, but it was worth every second. Lakes, mountains and countless trees appeared around every bend. With the number of stops I made at viewpoints, I’m relieved I made it to town before sunset.
When I did meander into Redmond, I was tired and hungry. Luckily, SCP Hotel Redmond had everything I needed. They’re a values-based hotel with locally sourced plant-centric dining, comprehensive recycling and compost and no single-use plastic.
When I arrived, I treated myself to a late dinner at Terra Kitchen. The next morning, I stopped by Provisions Market in the lobby, grabbed my go-to order (a chai tea and breakfast burrito) and headed west.
Of all my day trips, this was the one I was most interested in being early for. Driving between Mt. Washington and Three Finger Jack, I escaped into Oregon’s back country. Past Detroit and Breitenbush, I arrived at the trailhead for Bagby Hot Springs. The 1.5-mile hike flew by as I anticipated the fresh, hot spring water. I spent the morning lounging in one of Oregon’s natural wonders before heading back to my car for a packed lunch.
Delicious Food, Amazing Music and Better Friends
I wanted to stay longer, but Pickathon started that night, and I needed to get going. I got in the car one more time and drove up to Portland. I dropped off my car and took the MAX Green Line to the Foster Road MAX Station. The festival offers a shuttle service from there, which let me avoid buying a parking pass. I took a seat, surrounded by fellow music lovers, and we were off to Happy Valley.
Each morning, I woke up in my hammock to the sound of music. Following it down the hill, I found local restaurants serving their food. Oregon originals like Ate-Oh-Ate, Poblano and Dump City Dumplings provided everything. From my early-morning tea to my late-night snacks, Pickathon had some of Oregon’s top culinary offerings.
On Saturday night, I leveled up my dining experience with Pickathon’s “Curation” series. Curation pairs Portland’s notable culinary minds with local drinks and festival musicians. I lucked out, eating a multi-course meal from a six-time James Beard Award finalist. Chef Cathy Whims, a Portland local, prepared some of her signature Italian cuisine for us. With it, we drank Oregon’s own Maloof Wines and listened to music from Fruit Bats (one of the festival headliners).
While Pickathon was the destination, my journey there was just as wonderful. The only challenge will be finding a way to top it this year.
If You Go:
- Getting there: Attendees can drive, take rideshares, take the shuttle, or bike. Parking passes are $105 each or $125 for oversized vehicles. Free bike passes are available from Pickathon, allowing attendees to secure their bike inside the Pickathon grounds all weekend.
- Lodging: Pickathon offers three different options for overnight guests.
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- Camping in the woods: This option is included with any weekend ticket, and features cool neighbors, natural shade, easy access to shows and a truck to carry your gear up the hill.
- Vehicle camping: If you’re arriving in a vehicle big enough to sleep in, you can upgrade your tickets to include a vehicle camping pass.
- Hotels off-site: Attendees who don’t mind commuting to Pickathon can grab a room at any nearby hotel. Pickathon recommends three hotels that are all within 5 miles of the shuttle pick-up. There’s also a dedicated rideshare drop-off zone for visitors that want direct access.
- What to bring: I’d recommend packing your yoga mat, some food staples to save some money, and your lightest gear (you’ll have to carry it from the gear drop to your campsite). Leave your pets and your personal alcohol at home, as both are prohibited. If you have more questions, Pickathon has a full list of essentials on their website.
- Waste: Pickathon is a zero-waste festival and has stopped offering single-use cups, plates and bowls. Consider bringing your own or picking up a commemorative steel cup on-site. Once you use a dish, you can clean it at one of the rinse stations and have it ready to use again.
- Local resources and fun: If you’re passing through Happy Valley on your way to Pickathon, many attendees stop at the local New Seasons to stock up on last-minute supplies. If you have some extra time you can hike Scouters Mountain, which offers great views of Mt. Hood and is a 4-minute drive from Pendarvis Farm.
