Why we started
In 2011, Aoife Brennan and Marcus Hale were leading trips for a large operator and kept noticing the same problem: the best parts of the Pacific Northwest were being rushed past. A minibus of 48 people would stop at Multnomah Falls for 20 minutes, then race to a winery that served the same three wines as every other stop. So they started Pussywillow Journeys in a spare room on Southeast Ankeny Street with one rule: keep groups small enough that the person driving can also be the person cooking dinner. Fourteen years later, we still plan every itinerary from Portland, with six full-time guides, one part-time reservations coordinator, and a printed map of Oregon on the wall that has more coffee stains than pushpins. We have never run a trip we would not take ourselves.
Our principles
Four commitments shape every trip we sell and every trip we turn down. They are the reason we can promise a certain kind of week in a place we know block by block.
- Group size
- Never more than eight guests, with one guide. Nine is a bus. Eight is a dinner party.
- Pace""
- Maximum six hours of moving time a day, and one full unscheduled afternoon built into every itinerary after day three.
- Local spending
- At least 70 percent of each tour's food and activity budget goes to businesses within 60 miles of where we sleep. In 2025 that meant 143 different independent farms, bakeries, boat operators and galleries on our schedules.
- What we do not do
- No hotels with more than 40 rooms. No restaurant chains. No commissions from gift shops. No trips to the Tulip Farm in April, when the surrounding roads are gridlocked. No hunting or high-speed jet boat tours.
How the years added up
A narrow record of the decisions that shaped the company, kept in order from the first office key to the most recent guide hire.
- 2011 — First publicly advertised trip, "Waterfalls and Wallowa," two guests, one borrowed Chevy Astro.
- 2013 — Second guide hired. Senior trips director Talia Moreno introduces the fixed-rhythm itinerary that we still use.
- 2016 — Move to NW Couch Street office. Rent is $1,650 a month for 340 square feet, marker-drawn map stays.
- 2019 — Reach 1,000 total guests since founding. Begin the no-more-than-40-room policy.
- 2022 — Shop purchases totaled 214 acres of sweet potatoes, 52 cases of jam, and nine hand-carved canoes. We rounded.
- 2025 — Hire sixth guide, Sam Okonkwo. Cap any single-month guest count at 19 to keep wait times patient.
Behind the front window
You do not need a storefront to plan a trip today — everything happens at a few wooden desks and three phones. The window is where the light comes in and where the map catches it.
"We are trying to run the kind of travel company where the person you call at 4 p.m. on a Friday is the one who will pick you up at the airport next month." — Aoife Brennan, co-founder