Our Oregon & California Redwoods Road Trip
From city tunnels to crater swims and coastal sunsets
Portland, Oregon
Our trip began in Portland, a city layered with creativity, history, and just enough weird to keep things interesting. One of our first stops was the Portland Underground on a haunted tunnels tour. Originally built in the late 1800s to transport goods from the waterfront to downtown businesses, the tunnels later became tied to Portland’s darker history of shanghaiing—when sailors were kidnapped and forced onto ships. Walking beneath the city felt like stepping into a hidden chapter of the past.
We lightened things up with a stop at Wonderwood Mini Golf, a playful, art-filled indoor course that was unexpectedly fun. Before leaving the city, we grabbed a classic Pacific Northwest meal at Jake’s Crawfish, a longtime Portland institution known for its seafood and timeless atmosphere.
Bend, Oregon
From Portland, we headed east to Bend to visit my middle sister and slow into high desert life. Bend sits along the Deschutes River and was once a major logging town before evolving into one of Oregon’s most beloved outdoor hubs.
Mornings started with coffee from Fox & Fern Coffee, a spot that perfectly captures Bend’s relaxed rhythm. We spent time soaking in views of Mount Bachelor, an iconic stratovolcano and centerpiece of Central Oregon’s recreation scene.
We also stopped for drinks at McMenamins Old St. Francis School, a former Catholic school turned iconic Oregon gathering spot. Known for its cozy bars, murals, and historic character, it was the perfect place to unwind with a drink and soak in a little Pacific Northwest nostalgia.
Crater Lake National Park
From Bend, we drove south to Crater Lake National Park, home to the deepest lake in the United States. The lake was formed over 7,000 years ago after the collapse of Mount Mazama, leaving behind impossibly blue water fed only by snow and rain.
Our visit coincided with Ride the Rim 2025, an annual event that closes the rim road to cars and opens it to cyclists and pedestrians. Experiencing Crater Lake without traffic—just quiet, wind, and wide-open views—was unforgettable.
Yes, we swam in Crater Lake (freezing, but worth it) and stayed nearby at Alice’s Cottage, a cozy Airbnb tucked into the forest that felt like the perfect place to rest and reset.
Redwoods National & State Parks & Northern California Coast
Crossing into California, we entered Redwood National and State Parks, where ancient redwood trees rise hundreds of feet into the sky. Some of these trees are over 2,000 years old, making the forests feel quiet, humbling, and almost sacred.
Just north of the Redwoods, we stopped in Crescent City to visit Battery Point Lighthouse. Built in 1856, the lighthouse sits on a rocky island that’s only accessible during low tide. Walking across the exposed shoreline to reach it felt surreal, especially knowing it once guided ships through one of the most dangerous stretches of the Pacific Coast.
We continued along the coast to Arch Rock, a dramatic sea arch shaped by centuries of wind and waves—one of those places where you just stand still and watch the ocean do its thing.
Newport & the Central Oregon Coast
Back in Oregon, we followed Highway 101 to Newport, where we stayed aboard the Newport Belle, a historic houseboat Airbnb permanently docked in the harbor. Falling asleep to the sound of water and waking up wrapped in coastal fog was such a unique experience.
We visited the Oregon Coast Aquarium, watched the sea lions lounging on the pier, and warmed up with chowder from Rogue Brewery, one of Oregon’s most recognizable craft breweries.
Nearby stops included Heceta Head Lighthouse, built in 1894 and still shining today, and Agate Beach, where we caught one of the prettiest sunsets of the trip.
Northern & Southern Oregon Coast
We continued north to Cannon Beach, home to wide sandy beaches and the iconic Haystack Rock.
One of the more personal stops of the trip was Shiba Wichern Cellars, where we got to see how Shawn’s friend makes wine—one of those behind-the-scenes experiences that makes travel feel truly special.
Final Stops & Favorite Bites
Before wrapping up, we stopped at pFriem Family Brewers, a favorite known for its thoughtful brewing and river views—an ideal final pause before heading home.
Why This Trip Stayed With Us
This journey through Oregon and the California Redwoods reminded us why we love slow travel—layered history, wild places, meaningful connections, and moments that ask you to stay a little longer. From riding the rim of a volcanic lake to standing beneath ancient trees and walking to a lighthouse at low tide, it was the kind of trip that stays with you long after the road ends.
