Your Guide to an Oregon Trail Road Trip

The Oregon Trail, a 2,000-mile trek starting from Independence, Missouri and ending in Oregon City, Oregon, was a perilous journey in its time. The initial path was charted by Lewis and Clark from 1803 to 1806, but it was missionaries who traveled the route in significant numbers during the ensuing decades with the aim of converting Native Americans to Christianity.

Later, the Oregon Trail saw hundreds of thousands of pioneers and gold miners seeking their fortunes and starting anew on the western frontier. However, by the end of the century, the trail was largely abandoned due to the advent of the railroad, which made the same journey possible in a mere week.

The Oregon Trail was a treacherous 2,000-mile journey with danger lurking at every turn. Roughly one in ten travelers succumbed to contaminated water, diseases, harsh weather, attacks by wild animals, and skirmishes with Native American tribes who had lived there for millennia.

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To avoid the extreme weather conditions, settlers had to embark on the journey no later than April or May. At its peak, so many pioneers traveled the trail simultaneously that they had to follow each other in a single-file line. The Oregon Trail lost its popularity towards the end of the 19th century when the same journey could be accomplished in just a week by taking the railroad.

Embark on a road trip along the Oregon Trail, which commences at Cannon Beach on the stunning Oregon coast. Cannon Beach is a captivating town with such charm that you may never want to depart. The most renowned attraction in town is the majestic Haystack Rock, which stands at 235 feet tall and rises from the shoreline.

The downtown area of Cannon Beach is quaint and offers a plethora of boutiques and art galleries to explore. For lunch, indulge in some of the best food and beer at Public Coast Brewing Company. Afterward, take a stroll along the picturesque paved trails at Ecola State Park to behold views of the historic Tillamook Rock Lighthouse. Spend the night a stone's throw away from Haystack Rock at Surfsand Resort, where you can relish first-rate amenities such as a pool, restaurant, fitness center, and beachfront cabana service during the season.

After leaving the charming town of Cannon Beach, your next stop is the vibrant city of Portland. Stay at The Porter Portland for a luxurious experience within walking distance of the city's top attractions. The hotel boasts a pool, a rooftop bar with breathtaking views, and several dining options. Take a leisurely stroll to Tom McCall Waterfront Park to admire the Willamette River, and don't miss out on the opportunity to visit Powell's City of Books, the world's largest independent bookstore.

Other must-see attractions include the Portland Japanese Garden and the End of the Oregon Trail Interpretive Center in nearby Oregon City. For an unforgettable meal, indulge in traditional Italian cuisine made with fresh Pacific Northwest ingredients at Terraane Italian Kitchen and Bar, located in your hotel.

Your next stop on the Oregon Trail Road Trip will be the beautiful and vibrant city of Portland. The Porter Portland is a stunning hotel with fantastic amenities, including a pool, a rooftop bar with breathtaking views of the city, and numerous dining options. From the hotel, you can take a short walk to the Tom McCall Waterfront Park for a leisurely stroll along the Willamette River, and visit Powell's City of Books, the world's largest independent bookstore.

Don't miss the Portland Japanese Garden and the End of the Oregon Trail Interpretive Center in nearby Oregon City. Treat yourself to an unforgettable meal of traditional Italian cuisine with fresh Pacific Northwest ingredients at Terraane Italian Kitchen and Bar.

Your journey continues with a detour to the Historic Columbia Scenic Highway, the oldest scenic route in the country, with stunning views of the Columbia Gorge, Multnomah Falls, and Hood River, a charming town known for kite surfing and breweries. The Columbia Gorge Discovery Center and Museum in The Dalles is a great place to learn more about the history and wildlife of the area. Don't miss the grilled cheese on sourdough at Sunshine Mill, which also offers excellent wine tastings.

From The Dalles, head down to Madras and take a short detour to the picturesque mountain town of Bend. There, you can hike, explore underground caves, kayak, and enjoy the downtown area filled with shops, restaurants, and breweries. Brasada Ranch, located outside of Bend in Powell Butte, is the perfect place to stay, offering hotel-style rooms or private cabins with spectacular views of the Cascade Mountains, multiple swimming pools, hiking trails, tennis courts, fishing ponds, horseback riding, great restaurants, and more.

As you continue your journey, you'll drive through mostly rural and sparsely populated regions. Don't miss the John Day Fossil Beds National Monument in Kimberly, where you can marvel at ancient fossils of extinct plant life and animals such as saber-tooth cats, set against colorful bluffs and ancient hills.

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