7-Nights Extraordinary Oregon Road Trip - Road Trips from $1,208

Itinerary Details

Day 1: Arrive in Portland

Arrive at Portland International Airport and pick up your car rental. Located on the northwestern border of the state of Oregon, Portland lies in a magnificent setting between the sparkling waters of the Columbia and Willamette Rivers, 78 miles (126 km) from the Oregon Coast. Portland is a year-round, always-evolving city that is home to a mindful community dedicated to keeping it sustainable, innovative and accessible. There is an enviable public transit system, tax-free shopping and enormous in-city parks offering dozens of cultural attractions. Upon arrival, proceed to your hotel located in the heart of the city where you will be able to explore most of Portland's eclectic neighborhoods on foot. Walk to Pioneer Place shopping district, browse Powell's City of Books, the world's largest bookstore or take a stroll in Washington Park, a destination in its own right: here you will find the Oregon Zoo; Hoyt Arboretum, a glorious, forested place full of flora from around the world; the International Rose Test Garden, the oldest one in the United States; and the Portland Japanese Garden, which includes five varieties of gardens. Overnight Portland.

Hotel: The Benson Portland, Curio Collection by Hilton (4 Star Rating)

The iconic Benson Hotel is the city’s only luxury hotel that blends the charm and civility of the old world with the elegance of contemporary European design and mindful service.

Built by legendary innovator and philanthropist Simon Benson in 1912, the hotel features original Italian marble floors, Austrian crystal chandeliers, and the largest collection of Circassian walnut within one building. The Benson is truly the last of its kind, with a multi-million dollar renovation completed in 2023. Curated B&B Italia furniture now welcomes guests throughout the lobby. Our Palm Court Restaurant & Bar — with Culinary by El Gaucho — beckons guests to imbibe, gather and connect. We’ve refreshed our 12 meeting rooms and two dramatic grand ballrooms with new technology, lighting and design features with a modern simplicity, that in contrast, highlights the existing architecture of each space. Our 1,500 square foot fitness center has been expanded to include all new, state-of-the-art equipment and yoga studio.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Today, enjoy Portland by bike with the Downtown tour offered by Pedal Bike Tours. (Admission not included) Hop on well-traveled bike lanes stopping to admire the views of downtown, the river and the city's many bridges, then ride along the waterfront past the brick and cast iron fronted buildings of Old Town built in the 19th and early 20th century, head into Chinatown where the streets once teemed with immigrants from all over the world and roll through the Pearl District where turn-of-the-century warehouses have been turned into art galleries, shops and restaurants surrounded by soaring glass residences. Don't miss lunch at one of the city's food cart pods, huge collections of eateries banded together in one spot. Top it off - morning or night - with a stop at famous Voodoo Doughnut (for the bacon maple) or Blue Star Donuts (for the blueberry bourbon basil). After pedaling through the city, we recommend visiting Knot Springs in inner Northeast Portland: an idyllic place to experience Oregon's rejuvenating soaking pools and hot springs, their "Knot Springs Ritual" is a seven-step treatment that includes an exfoliation shower, a warm and hot pool soak, a cold plunge, a sauna, wellness-boosting steam and - wait for it - nap time! Overnight Portland.

Hotel: The Benson Portland, Curio Collection by Hilton (4 Star Rating)

The iconic Benson Hotel is the city’s only luxury hotel that blends the charm and civility of the old world with the elegance of contemporary European design and mindful service.

Built by legendary innovator and philanthropist Simon Benson in 1912, the hotel features original Italian marble floors, Austrian crystal chandeliers, and the largest collection of Circassian walnut within one building. The Benson is truly the last of its kind, with a multi-million dollar renovation completed in 2023. Curated B&B Italia furniture now welcomes guests throughout the lobby. Our Palm Court Restaurant & Bar — with Culinary by El Gaucho — beckons guests to imbibe, gather and connect. We’ve refreshed our 12 meeting rooms and two dramatic grand ballrooms with new technology, lighting and design features with a modern simplicity, that in contrast, highlights the existing architecture of each space. Our 1,500 square foot fitness center has been expanded to include all new, state-of-the-art equipment and yoga studio.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Today, head east towards Mount Hood, where the wild and the wonderful are waiting for you. The mountain is approximately 70 miles (113 km) away from downtown Portland and there are two route options: Interstate 84 through the Columbia River Gorge or Highway 26. Either way, you will get to the Mount Hood Scenic Byway, a breathtaking route around the edge of the mountain. Mt. Hood is the highest point and mountain peak in the state of Oregon, and the second most climbed mountain in the world (second only to Japan's holy Mt. Fujiyama). This dormant volcano offers endless possibilities with hiking trails, spots for camping and fishing, and nearly year-round skiing. Make your way back to the Portland region and experience Oregon City, the state's first capital and the end of the Oregon Trail, one of the prettiest little cities within a stone's throw of Portland. At 130 feet (39 meter) high, the Oregon City Municipal Elevator offers the best view in town: the elevator is one of only four municipal elevators in the world and the only "vertical street" in North America. Locals call it "Elevator Street." End your day at the Oregon City Brewing Company, a new American brewery that is product of the Oregon craft beer culture shaped by Oregon City values: quality craftsmanship and a spirit of innovation. Overnight Oregon City.

Hotel: Best Western Plus Rivershore Hotel (3 Star Rating)

Nestled on the Willamette River, this hotel is fantastic for boating, tubing and taking in the gorgeous Northwest. At our Oregon City hotel, outdoor recreation options abound including hiking the numerous trails and even clamming on the coast which is a day trip away. With easy access right off of I-205, our property is convenient for vacationers and business travelers alike.

Our property is river front, making it great for a relaxing getaway or romantic escape. There's an on-site bar and restaurant so guests don't have to go far for a great meal. Fishing, boating and river activities are steps away, and our friendly staff members are happy to help you put together the ultimate outdoor adventure. We're also located in a historical site at the end of the Oregon Trail, and there's plenty for history buffs to explore.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Continue your journey through the Portland region by exploring the Tualatin Valley's rich agricultural heritage and character through art, markets and outdoor activities. The Quilt Barn Trail includes a series of 59 painted wooden quilt panels that tell a story about local farms and agricultural businesses. Some of Oregon's best fresh local produce, artisan food products and alcoholic beverages can be found at the Beaverton Farmers Market, which also offers live entertainment. Take a more hands-on approach at Smith Berry Barn, where visitors can pick blueberries, strawberries, raspberries, blackberries and more. Outdoor enthusiasts can choose from a wide range of activities: ride the Tualatin Valley Scenic Bikeway; kayak on the peaceful Tualatin River; or enjoy the Banks-Vernonia State Trail, a 21-mile (33km) tree-lined multi-use trail that is open year-round to walkers, joggers, cyclists and horseback riders: it was the state's first rails-to-trails project and it attracts tens of thousands of people through open glades of the green, pine-scented forests and across babbling streams. Nothing pairs quite as well with relaxation and peaceful scenery as a bottle of fine wine at the end of your day: luckily, there are 30 amazing wineries scattered around the area! Overnight Beaverton.

Hotel: Hyatt House Portland/Beaverton (3 Star Rating)

Settle in at the newest hotel in Beaverton! Nestled in the bustling The Round, Hyatt House Portland / Beaverton offers an easy weekend getaway or a home base to explore city life in Portland. Experience one of Beaverton’s most exciting hubs and stay steps from trendy dining, shopping, and The Plaza, the popular, piazza-like center of the neighborhood. Enjoy being a short drive away from corporate campuses in Hillsboro like Nike and Intel Corporation.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Today, you will embark on a road trip to the Oregon Coast: 362 miles (585km) of Pacific coastline that offer panoramic views of rugged cliffs, evergreen forests, Sahara-like dunes and boundless sandy beaches. You will pass through beautiful quaint towns, such as Tillamook: located amidst a tangle of rivers and farm fields, Tillamook is renowned for its agriculture that stewards and cultivates the region's natural beauty. A highly successful dairy industry has led the name Tillamook to be frequently associated with dairy products, and tours of the Tillamook Creamery are one of the most popular attractions in town. Restaurants here think local, putting farm and ocean-to-table ingredients to good use in their dishes. From here, head north to Kelly's Brighton Marina on the majestic Northern Bay, a premier spot for crabbing, fishing and more that is worth the detour. Enjoy the cool, crisp breeze as it rolls off the pristine Bay and listen to the delightful sounds of nature that surround you. As you head south towards Newport, make sure to stop in Pacific City: sitting on the Three Capes Scenic Loop with stunning Cape Kiwanda as its headland, Pacific City is a beautiful beachfront town offering plenty of outdoor pursuits. It is also the birthplace of Pelican Brewery, located right next to the sand. Overnight Newport.

Hotel: Shilo Inns Newport Oceanfront (3 Star Rating)

Experience coastal comfort at Shilo Inns Newport Oceanfront Hotel with breathtaking views from every room, free amenities, and just steps to the ocean.

Conveniently located just moments away from Yaquina Bay and the Oregon Coast Aquarium, the hotel provides the perfect base for exploring the wonders of the coast. Whether you're seeking a romantic getaway, a family vacation, or a corporate retreat.

This ocean front hotel features 179 beautifully appointed guest rooms, each with a spectacular view of the Pacific Ocean, south jetty and to the north, the Yaquina Head Lighthouse. Kids under 18 always stay free with an adult at Shilo Inns. Dogs welcome with nominal fee.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Newport could really only exist on the Oregon Coast: few communities embody the offbeat vibe of the Coast better, and Newport's unconventional attractions, lighthouses, and aesthetic make it immensely memorable. Bordering on both the Pacific Ocean and the large Yaquina Bay, Newport is so many things combined into one remarkable place. An active working waterfront, the Historical Bayfront area is home to one of Oregon's largest commercial fishing fleets. It is also an intriguing cultural district, with shops, art galleries, chowder houses, and restaurants right next to fish processing plants and historic buildings. A second distinct area of town, Nye Beach, was the number one attraction on the Coast during the early 1900s, and is still a popular haven for the arts. Newport has not one but two lighthouses - the original lighthouse on Yaquina Bay, and a second lighthouse built in the late 1800s on Yaquina Head, north of town. At 93 feet (28 meters) tall, the Yaquina Head Lighthouse is the tallest active lighthouse in Oregon. The Oregon Coast Aquarium is world class and grants passage to mesmerizing turquoise tunnels and large tanks filled with colorful fish, sharks, and even stranger creatures. Not to be outdone on striking landmarks, the Yaquina Bay Bridge is an iconic, art-deco arch bridge on Highway 101 that spans the bay. Overnight Newport.

Hotel: Shilo Inns Newport Oceanfront (3 Star Rating)

Experience coastal comfort at Shilo Inns Newport Oceanfront Hotel with breathtaking views from every room, free amenities, and just steps to the ocean.

Conveniently located just moments away from Yaquina Bay and the Oregon Coast Aquarium, the hotel provides the perfect base for exploring the wonders of the coast. Whether you're seeking a romantic getaway, a family vacation, or a corporate retreat.

This ocean front hotel features 179 beautifully appointed guest rooms, each with a spectacular view of the Pacific Ocean, south jetty and to the north, the Yaquina Head Lighthouse. Kids under 18 always stay free with an adult at Shilo Inns. Dogs welcome with nominal fee.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Today, you will head towards Oregon's Wine Country, home to two-thirds of the state's wineries and recognized as one of the premier Pinot noir-producing areas in the world. The mid-Willamette Valley Food Trail offers a self-guided journey through a bountiful land of historic farms and trailblazing spirits. In Albany, we suggest visiting Midway Farms to peruse the farm stand and join a cooking class, cider pressing party or twilight yoga. Continue on to discover maker culture on display at Albany's Honeybrine Market, where local artisan products and frequent events are hosted in charming warehouse space. Stop at Thompson's Mills State Heritage Site for a free guided tour of Oregon's last water-powered mill, built in the mid-19th century. Another must-see is the Albany Carousel & Museum, one of the biggest draws in the Willamette Valley, with historic machinery and a whimsical herd of animals carved by hand from the museum team of volunteers. For an unparalleled wine tasting experience, we recommend heading north to the Willamette Valley Vineyards Tasting Room, an award-winning winery where you can enjoy food and wine pairings in a relaxing setting with cozy fireplaces, an expansive patio, spacious courtyard and a 65-foot lookout tower as you take in the sweeping views of the vineyard and valley. Overnight Salem.

Hotel: Best Western Plus Mill Creek Inn (3 Star Rating)

The 2023 TripAdvisor® Certificate of Excellence winning, pet-friendly Salem, Oregon hotel welcomes guests! Enjoy the convenience of being in a prime location, near the State Capitol and the Salem Conference Center, business travelers and history buffs alike enjoy staying at the Salem hotel. Our unbeatable location, right off Interstate 5 and Highway 22, makes it easy for guests to explore the region. Spacious rooms complemented with an indoor pool, hot tub and private sauna make relaxing after a day of exploration a breeze.

From the Oregon Gardens to nearby Spirit Mountain Casino, there's something for everyone in this part of Oregon. The Salem, Oregon hotel is close to Willamette University for guests visiting the campus, and the famous Oregon State Fair is a favorite activity every year. The small-town vibe of Salem meshes perfectly with the conveniences of a larger city.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap

Make your way to the airport for your flight home unless you plan to extend your stay in Portland.

Rental Car: Hertz - Portland Intl Apto Portland Intl Ap