A Whimsical PNW Troll Trail: A Family & Friends Road Trip

The Pacific Northwest Troll Trail ended up being one of the most unexpectedly joyful trips I’ve taken with my kids, our friends, and their dog. The trail is a collection of giant wooden trolls created by Danish artist Thomas Dambo, each built from recycled materials and placed in natural settings to encourage exploration, play, and a deeper connection with the outdoors.

We started in Portland with a visit to Olle Bolle, a big, friendly seated troll tucked into a neighborhood park. He has his arms stretched outward as if he’s inviting you in for a hug, and starting the trip with him set the tone perfectly.

Olle Bolle, the Portland troll who kicked off our Troll Trail adventure.

Our first forest troll after Portland: Jakob Two Trees, nestled deep in the Issaquah woods.

From there, we drove north and our next major stop was Issaquah to find Jakob Two Trees, hidden among mossy evergreens. After that, we continued to Seattle, where we based ourselves for the rest of the trip. We hopped between Bainbridge Island and Vashon Island by ferry, which was such an enjoyable experience. Recently, having moved from the desert to the PNW, my kids and I loved being on the water and enjoying the wonderful views. Our next Troll was Pia the Peacekeeper on Bainbridge Island. It felt like she was waiting for us in her own quiet clearing. After that, we took a ferry to the Vashon Troll and also walked around Point Robinson Lighthouse. This ended up being one of my favorite moments of the entire route for the views and wonderful walks together.

Ferry views of Seattle’s skyline.

Coastal calm and a glimpse of Rainier from Vashon.

For our home base, we stayed at Staypineapple Hotel FIVE in Seattle, and it was such a great fit for this kind of trip. The rooms were bright and cozy, the beds were ridiculously comfortable, and the hotel’s playful vibe matched the spirit of the Troll Trail perfectly. It was also incredibly pet‑friendly, which made traveling with our friends’ dog so much easier. Being close to Pike Place Market, the ferries, and the waterfront made it the perfect jumping‑off point each morning.

Seattle’s market magic after dark.

We completed this trip in just two days, and it worked beautifully. The trolls are easy to reach, the walks are short, and the ferries give you natural breaks to enjoy the water and grab snacks. But if someone has more time, this route becomes even richer. Bainbridge Island has wonderful wineries and tasting rooms that make for a relaxing afternoon, and Vashon has quiet beaches and local shops that are worth lingering in. Staying longer in Seattle also opens up time for classics like the Space Needle, Chihuly Garden and Glass, the Seattle Great Wheel, or simply wandering the waterfront parks. A long weekend gives you space to explore at a slower pace and enjoy more of what each stop has to offer.

Overall, this trip is perfect for anyone who wants something lighthearted, scenic, and a little whimsical. It’s accessible for all ages, easy to customize, and full of those small, memorable moments—standing under a giant wooden sculpture, watching the ferry cut across the Sound, or wandering down to a quiet lighthouse at sunset. It’s the kind of trip that invites curiosity and connection, and it’s one I love recommending because it shows off the very best of the Pacific Northwest.

A peaceful stretch along the Bainbridge waterfront before our next troll stop.

• Ferries on this route are first‑come, first‑served, and arriving about 20–30 minutes early usually keeps things running smoothly.

• Parking is straightforward at most troll locations, and the walks are short and manageable for all ages and abilities, though you’ll want comfortable shoes since the paths range from paved to natural trails.

• Cell service can be spotty on Bainbridge and Vashon, so it helps to download maps ahead of time.

• Weather in the Pacific Northwest changes quickly, so packing layers and a light rain jacket makes the trip more comfortable.

• The area is very dog‑friendly, with many trails, beaches, and even Staypineapple welcoming pets.

• Weekends can get busy, so starting early or stretching the trip over a long weekend keeps the experience relaxed and enjoyable.

For more inspiration and insider recommendations, visit our Pacific Northwest page.