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The Oregon Trail

by Kate Calamusa

Begin Your Journey In:


Nestled just over the Washington-Oregon state border, the port town of Astoria is steeped in both maritime history and small town charm, making it an ideal spot for a sojourn to precede a trip down the coast. Chockablock with forts, museums, breweries, boutiques, and restaurants, the sweet town sits at the mouth of the mighty Columbia River, with Victorian-era houses dotting the hillsides that overlook the water and the towering Astoria-Megler bridge. (This iconic structure—the longest continuous truss bridge in North America—is accessible for boaters to float under 365 days a year, but this month, on October 8th, is the only day a year that pedestrians can make the trek across as part of the annual Great Columbia Crossing 10K event.)

More stunning views of the bridge can be found along the riverwalk trail that traverses the city’s picturesque main corridor located just off Highway 30. Running almost 13 miles in length, this trail meanders its way by myriad eateries, boutiques, hotels, and marinas, all with spectacular scenery and views. Speaking of marinas, captains looking to drop an anchor can do so at the East Mooring Basin located near the eastern edge of the riverwalk, or alternatively, boaters can find water access and convenient moorage near the base of the bridge at the West Mooring Basin facilities. Those looking to instead hang their hats on dry land would do well to check out the Bowline Hotel. This nautical- themed boutique establishment not only offers luxe accommodations, but also a stellar lobby bar known as The Knot, where the creative cocktails flow freely, and the locally sourced fare is top notch. (Trust us and order the housemade herb-kissed onion dip served with the state’s beloved Tim’s potato chips to start.)

There’s also bounty of brews to enjoy while in town: The town’s oldest brewery, Astoria Brewing Company, continues to stake its claim as one of the best places to stop for a solid brew from its prime location on Pier 11; Rogue Brewery’s Pier 39 Public House offers a variety of handcrafted beers on tap to pair with gastropub faves like burgers and fish n’ chips at their rustic spot on the docks; and Fort George Brewery on Duane Street boasts a large, dog-friendly patio for those crisp, sunny fall days, a downstairs eatery for those wet days, a merch and beer-to-go shop; plus tucked away upstairs at the convivial establishment’s pizza pub you’ll find what many locals argue to be the best ‘za in town.

But, perhaps, the one can’t-miss stop in town for mariners is the Columbia River Maritime Museum that houses a 30,000-object collection covering fishing, shipping, and military history in their harbor- front building. Here, you can discover the many stories of the legendary Columbia River Bar, one of the most dangerous passages in the world, as well as visit the historic Lightship Columbia. Functioning as a floating lighthouse to mark the mouth of the river from 1951 to 1979, this red-hulled vessel returned to the museum in late 2022 after an extensive renovation. Big things are also on the horizon for CRMM as a whole: The museum recently announced it is moving forward on a $30 million expansion of its campus that will feature a second exhibit hall. (More details on visiting Astoria can be found at: travelastoria.com.)

Oregon Travel Feature - Wreck of the Peter Iredale
Photo by Intricate Explorer Photography

Make Way For:


Departing from Astoria, and making way towards the greater Pacific to the west, your cruise will take you first by Warrenton and darling little Hammond, where you can find another very accessible boat launch, before you sail on by Fort Stevens State Park. Sprawling 4,300 acres, this park contains expansive beaches, hiking trails, campgrounds, and a picturesque lake, and marks the site of a military installation once used to guard the mouth of the Columbia River. The fort saw service for 84 years, from the Civil War to World War II, and much of the remaining battery can be explored.

The park’s South Jetty viewing platform located at the northern edge of the park, and at almost the northernmost point of the state, is an excellent spot to watch ships as they enter and exit the bar, a journey that for centuries has been known to be treacherous in this larger area known as the Graveyard of the Pacific. (Though the construction of jetties, continual dredging of the bar, and GPS advancements have made this stretch much less treacherous for modern-day vessels, do still keep a weather eye out in these waters!) Fittingly, the park is perhaps best known as the site of the wreck of the Peter Iredale, a four-masted steel barque sailing vessel that ran ashore on October 25, 1906, on the Clatsop Spit about four miles south of the Columbia River channel. Though the ship has been further broken up by wind, surf, and sand that have worn away at her remains, there is still plenty left of her massive hull to marvel at on the beach. (More info on the park, and the wreck, can be found at: stateparks.oregon.gov.)

You Are Passing Through:


Heading further south, the rugged and rocky coastline is peppered by such soft sandy stretches as those found at DeLaura Beach, Strawberry Knoll, and Sunset Beach, before reaching Gearheart. In addition to the town’s two landmark golf courses—the 9-hole Highlands at Gearhart and the 18-hole Gearheart Golf Links—this laid-back enclave is home to the McMenamin’s Gearheart Hotel, an old-school style beach lodge that offers up a bevy of dining options, such as the Sand Trap Pub, an excellent spot to refuel after hitting the links or doing some beach combing.

Located just 2.5 miles south, you’ll find Seaside, Oregon, a town that fully embraces its kitschy, beachy-cool vibe. Coming from the oceanside, the Necanicum River estuary dissects the downtown, and is a fun route to explore via kayak or tender. The Quatat Park Boat launch is a great on-and-off spot for those small craft as it is located mere steps from the action going on the main drag, Broadway Street. There, the kids will be begging to ride the classic carousel at the Seaside Carousel mall, or adults might instead seek out the Times Theatre & Public House nearby. Half brewery, half theater, the popular spot is home to the Sisu Beer that is brewed on-site, as well as to a snack-friendly menu highlighted by such favorites as Sriracha candied bacon, fried dill pickle chips, garlic truffle fries, and pretzel knots. Definitely be sure to add on a side of the brewery’s signature cheese sauce, and do check ahead to see what’s playing on the big screen, from movies and concerts to sporting events. (More details for exploring these two towns can be found, respectively, at: visitoregon.com/cities/gearhart-oregon/ and seasideor.com.)

Tillamook Rock Lighthouse
Photo by Julie Olsen

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Leaving the sandier stretches behind as you wind along the rugged coastline, you’ll spot the dramatic Tiilamook Head, a towering, almost-1,000-foot-high cliff that marked the furthest point west surveyed by William Clark and Meriweather Lewis during their famed expedition, and today is a part of Ecola State Park. Over the course of a 3.6-mile loop trail that leads to the headland’s tip, hikers can take in the same breathtaking viewpoint that is rumored to have inspired the following words from Captain Clark: “I behold the grandest and most pleasing prospect which my eyes ever surveyed.”

Hiking aficionados can also spy the fabled Tillamook Rock Lighthouse from trails accessed from within the park, or the views of this island lighthouse are nothing short of spectacular from the water. Originally built in 1881, the 133-foot-tall outpost also known as “Terrible Tilly” seemingly juts straight up from its rocky outcropping located one mile west of Tillamook Head. It helped guide sailors around its inhospitable, wave-battered perch all the way until 1957, when the cost to maintain and transport goods and supplies to the location was deemed too expensive and it was decommissioned. Now privately owned, there’s no going inside, perhaps only enhancing its aura of mystery. (More details on visiting Ecola State Park, and spying the lighthouse, can be found at: stateparks.oregon.gov/.)

Haystack Rock
Photo by I Am the Dave Photography

You Have Arrived at:


Off in the distance from Tillamook Rock lies one of the most iconic natural landmarks in the state of Oregon—Haystack Rock. Situated just south of the main thoroughfare of Cannon Beach—a supremely sophisticated destination known for its thriving arts community, world-class dining, and luxurious hotels that boast views of the sight itself—the stunning rock outcroppings are a picture-perfect destination that offers even more surprises at low tide. Then, an entire other world is revealed in the rocky outcroppings, as beachcombers and marine life enthusiasts alike clamber up, over, and around to marvel at the shy sea anemones, colorful starfish, briny bivalves, and crusty crustaceans that call this area home. If the fall day is fine, and you can time it right, watching the sun dip behind the rocks as it splashes bright orange, pink and purple beams across the reflecting water would make for a very fitting capstone to your aquatic adventures. (More details on visiting Haystack Rock can be found at: cannonbeach.org.)

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