Top Oregon Cultural Tours

Discover the sightseeing highlights of Astoria, Oregon on this small-group tour. Get picked up straight from your accommodation to see the Astoria Column, Fort Astoria, the Goonies House, and more. Your guide shares stories about Astoria and its history, and you get their top tips on the best shops, restaurants, and events to check out when the tour is over.

Head out to the Columbia River Gorge for half a day of visiting cascading waterfalls and scenic overlooks with this tour from Portland. You'll visit Multnomah Falls, the highest waterfall in the state, as well as lesser-known falls throughout the region. You'll also have the chance to take mini-hikes in the area to get better views of waterfalls and the surrounding scenery.

This tour goes above and beyond your average city tour. Accompanied by an expert local guide who has deep insight into the history and culture of each district, this tour of Portland allows guests to stop at iconic Portland destinations and venture off the beaten path to discover exciting hidden gems of the city.

Escape the hustle and bustle of the city for the day on this guided tour to Multnomah Falls and the Columbia River Gorge Waterfalls. Travel along the historic Columbia River Highway National Scenic Byway and stop at the magnificent falls of Multnomah, Latourell, and Bridal Veil.

Explore Portland’s dark side on this thrilling outdoor walking ghost tour through the city’s most haunted historic sites. Led by expert local guides, you’ll uncover chilling tales of restless spirits, eerie legends, and true crime events that still haunt the streets today. Visit infamous locations like the Shanghai Tunnels, Old Town Pizza, and the Roseland Theater while hearing spine-tingling stories of Portland’s shadowy past. This tour is fully outdoors and runs nightly year-round—perfect for history buffs, ghost hunters, and anyone who loves a good scare. Walk the haunted streets of Portland—if you dare.

Visit many of Portland's prettiest parks and neighborhoods with this small-group tour of the city. Your local guide will tell you all about local history and culture while you visit downtown attractions such as Waterfront Park, Pioneer Square, and the South Park Blocks. You’ll also head up to Washington Park, site of the International Rose Garden, and to the historic Pittock Mansion for fantastic city views.

Immerse yourself in the scenery and story of Portland on this small-group sightseeing tour. With your naturalist guide, visit verdant urban parks, eclectic neighborhoods, and some of the city’s most treasured landmarks including the famous Powell’s Books. Enjoy a breakfast of tea and pastries as you traverse the city in style.

Creativity and natural splendor converge in Ashland, Oregon. On this 60-minute self-guided audio tour, discover the cultural heartbeat of this renowned community. Starting at the historic Plaza, you'll be immersed in the enchanting Lithia Park—designed by the creator of Golden Gate Park. You’ll follow the bubbling Ashland Creek deeper into the landscape, strolling past serene ponds and winding trails under a lush canopy of trees to find a quiet spot by the water. Emerging from the green, the route winds past Main Street’s historic landmarks to the Oregon Shakespeare Festival. You’ll taste the notorious Lithia mineral water, admire the Italian Butler-Perozzi Fountain, and marvel at the 110-foot tower of the Ashland Springs Hotel. Explore how the 1890s Chautauqua movement evolved into today’s world-class theater scene, highlighted by the Allen Elizabethan Theatre. Whether you’re a theater enthusiast or nature lover, this tour offers an insider’s perspective on Ashland’s magic.

Experience the best of Portland's chocolate and coffee scenes with this small-group walking tour, departing from downtown Portland. On this roughly 2-mile (3.2-kilometer) walk, you’ll visit popular coffee shops and lesser-known spots, learning about coffee and chocolate along the way. You'll also visit Azar Indulgences, where chocolate is paired with international wines.

There’s nothing better than exploring Astoria at your own pace, with a flexible itinerary tailored to your preferences. Step back in time and immerse yourself in the rich history of Astoria, Oregon's oldest American settlement. From its roots as a vital port city to its iconic landmarks, Astoria offers a perfect blend of history, natural beauty, and coastal charm. Discover its significant role in American exploration and maritime history, and enjoy breathtaking views of the Columbia River and the Pacific Ocean. This full-day tour takes you through the highlights of Astoria, offering a memorable journey through Oregon’s coastal heritage.

Immerse yourself in the beauty of Columbia River Gorge on this full-day trip from Portland to Mount Hood! With your small group, take a guided tour of such iconic Oregon destinations as Multnomah Falls and the famous Timberline Lodge, and enjoy lunch in the charming city of Hood River. Your tour also includes pickup from over 60 hotels in Portland and a private or small-group option.

The wine tour for wine and history lovers alike. If you love drinking wine and watching documentaries, you are our clientele! We provide several custom tour options to ensure your experience in Oregon wine country takes you to the best wineries while educating you on the history and culture of Willamette Valley. You'll be exposed to the best wines, amazing views, and beautiful stories. We specialize in customizing our trips so you visit only the best boutique wineries that represent the heart of Willamette Valley. Tours cover three wineries at a nice pace or four wineries at a quick pace (to be determined based on your preferences in discussion once booked). Lunch and tasting fees are not included. As you tour the valley in style, prepare for a fun, relaxing, and educational experience!

Taking this 1.5 mile (2.4 km) walk through the heart of downtown Portland with a local, experienced guide offers an exploration into the city's rich tapestry of history, culture, and innovation. Portland, noted for its quirk and progressive ideals, unfolds its stories through a series of iconic landmarks, bustling public squares, and artistic expressions that color its streets. Your guide will reveal Portland's past through the emerging landscape. Depending on your guide, your path may vary. Peak Tours is licensed and insured, local and family-owned, reliable and knowledgeable. We'd love to show you around!

Escape the city for an afternoon exploring some of greater Portland's most scenic falls. Travel along the Columbia River Gorge, home to the largest concentration of waterfalls in the country, stopping at the epic Latourell Falls and Multnomah Falls. Enjoy panoramic views from the Crown Point Vista House and hear about the local legends and natural history of the area from your guide.

See the highlights of Portland in just half a day on this private tour of Portland. You'll explore downtown Portland and the nearby NW 23rd shopping district, take in city views from the International Rose Test Garden and stroll through Lan Su Chinese Garden. If you come on a Saturday, you’ll visit the PSU Farmer’s Market.

See Portland like a local—by bicycle—with this guided tour. Your guide will take you on an eight- to 11-mile ride through town, past beautiful neighborhoods filled with flowers and across the river via the pedestrian- and bicycle-only Tilikum Bridge towards downtown, with a stop at a local donut shop for some sugary fuel along the way.

See the best of Portland's street art as you cruise around the city on a bicycle with this group tour, limited to 16 participants. After getting you fitted with a bike and a helmet, your guide will take you through the city's inner eastside, where you'll see gargantuan murals, check out interesting shops, learn about street art, and get the chance to take lots of photos.

Join us for an unforgettable adventure in Warrenton with our personalized guided tour! Experience an exciting scavenger hunt, explore the area's rich history, and enjoy breathtaking views. Witness the dramatic collision of the ocean and river and why it is called The Graveyard of the Pacific. Please remember to bring your own water bottle. In appreciation for reducing plastic waste, you'll receive a beautiful sand dollar.

ChatGPT said: Explore the natural beauty of Bend, Oregon on this 13-mile guided electric bike tour, perfect for casual riders and outdoor enthusiasts. This scenic route features a mix of paved and well-maintained gravel trails—about 5 miles unpaved—offering a relaxed ride through Central Oregon’s most picturesque landscapes. Take in panoramic views of the Cascade Mountains and ride along the Deschutes River while your local guide shares stories about Bend’s history and hidden gems. You'll pass through scenic parks, quiet neighborhoods, and make a stop at the beloved Sparrow Bakery in Northwest Crossing for a delicious local treat. Whether you're new to Bend or a returning visitor, this tour is a fun, active way to experience the city's stunning trail system and vibrant outdoor culture.

Explore Oregon’s rocky northern coastline, dotted with beaches and sea cliffs, on a scenic full-day trip from Portland. Travel the picturesque US Highway 101 through quaint beach towns, stopping in Cannon Beach, Ecola State Park, and Oswald West State Park. Enjoy panoramic coastal views, geological wonders, and wind-swept beaches without the hassle of self-driving, and learn more from your guide than you would going alone.

Our small group Eastside Coffee Roaster walking tour takes you to the makers who have called the neighborhood their home for decades, each with a different approach to coffee roasting and brewing. Across from downtown Portland, the industrial neighborhood has transformed from manufacturing and warehouses to the heart of passionate creators: artists, chocolate makers, food innovators, and every kind of free spirit. Portland has the most coffee roasters of any city in the world, and we would argue some of the most earnest and unique origins and barista artistry is happening right where Around Portland Tours makes its home. The tour in total is 1.5-3 miles (2-5 km) of walking, tasting and learning. You'll also discover a lot about Portland and how these artisans are nourished. We keep groups small, so you'll have an intimate experience with your passionate guides. Ask about larger private groups.

Combine two of Portland's quintessential experiences—cycling and food carts—with this small-group guided tour. You'll visit Portland's first major food cart pod, Cartopia, cycle through the flower-filled neighborhoods of Ladd's Addition and Hawthorne, and make a stop at the Scout Beer Tap House, all with a local guide to show you the way.

Want to see a bit of Portland, Oregon, and get some exercise while you're at it? Try a walking tour in the center of the city. Uncover Portland's weird and wonderful tales on every corner as you explore its buildings, parks, and streets. Your guide highlights the cultural evolution of the city and offers insights into its past, present, and future.