The 11 Best Hiking And Trekking Tours in Portland
Portland isn’t just known for its quirky neighborhoods and coffee scene—it’s a serious destination for outdoor enthusiasts. With lush parks, stunning waterfalls, and sweeping coastlines just a short drive away, the city offers a surprising variety of guided hiking experiences. Whether you’re craving a quick urban escape or an all-day adventure, Portland’s tour options provide something for every level of hiker, with plenty of local insights along the way.
From walking through massive Forest Park to marveling at Columbia River Gorge waterfalls and exploring Oregon’s rugged coast, each tour delivers a unique perspective on the region’s natural beauty. Plus, many tours include expert guides who share stories, flora, fauna, and local history, making your trek not just a walk but a richer experience.
1. Forest Park Urban Hiking Tour, Portland
At number 1, the Forest Park Urban Hiking Tour offers an immersive way to discover one of the largest urban forests in the U.S. This guided small-group outing explores Forest Park and Washington Park, starting from either the NW Portland area or near downtown, depending on your chosen time of day. The tour takes you along part of the famous Wildwood Trail, which stretches over 43 miles, and visits highlights like the Japanese Garden, Witch’s Castle, and the International Rose Test Garden.
What makes this tour stand out is its combination of urban walking with nature immersion, all guided by knowledgeable locals. The group is limited to 10, providing a personalized experience. With bottled water included, it’s perfect for those wanting a manageable walk that’s rich in sights and stories. Visitors rave about the friendly guide and the hauntingly beautiful foggy walk. This tour is ideal if you want quick access to Portland’s green heart without straying far from city life.
Bottom Line: A well-rounded, accessible introduction to Portland’s largest parks, perfect for city dwellers and visitors short on time but eager for outdoor scenery.
2. Silver Falls Waterfall Hiking Tour from Portland
At number 2, the Silver Falls Waterfall Hiking Tour takes you into one of Oregon’s most breathtaking natural areas. This 5 to 6-hour trip is focused on exploring the gorgeous waterfalls and scenic canyon formations within Silver Falls State Park. The tour includes visits to 3-6 waterfalls, with options for two medium-length hikes (around 1-2 miles each) or a longer 5-mile trek. Highlights include walking behind South Falls, passing Lava Tree Casts, and wandering through old-growth forests.
The tour’s strength lies in its detailed exploration of the waterfalls, combined with insightful commentary from guides who are passionate about Oregon’s geology and ecology. The reviews praise the marvelous scenery and guides’ expertise, with guests mentioning the beautiful greenery and multiple waterfalls—up to seven seen during the trip. The moderate difficulty suits most visitors, and the inclusion of a lunch adds value.
Bottom Line: This tour offers a comprehensive and scenic day out, packed with waterfalls and forest views, making it a top choice for nature lovers.
3. Cannon Beach Hiking Tour on the Oregon Coast
Number 3 features the Cannon Beach Hiking Tour, a full-day coastal adventure. The trip includes a visit to Haystack Rock, famous from movies like The Goonies, along with hikes through old-growth forests and scenic coastal vistas. After soaking in the views, you’ll enjoy a lunch stop in the charming town of Cannon Beach, with plenty of recommendations for local treats like cinnamon rolls and seafood.
What makes this outing distinctive is its blend of coastal scenery and forest hikes, plus the chance to see seabirds and explore the rock formations up close. The drive itself takes about 1 hour 20 minutes through lush forests and mountain passes. Guests appreciate the informative narration about local history and the time allocated for exploring shops and beaches.
Guests consistently mention the excellent guide and the perfect balance of sightseeing and hiking. Suitable for those wanting a relaxed pace with plenty of coastal charm, this tour is ideal for families or travelers wanting a comprehensive day at Oregon’s iconic coastline.
Bottom Line: For a mix of beach, forest, and small-town charm, this tour delivers a memorable taste of Oregon’s coast.
4. Silver Falls Hike
Number 4 is the Silver Falls Hike, a full-day, 8-hour guided adventure perfect for those seeking an up-close waterfall experience. The 5.7-mile Trail of Ten Falls takes you past multiple waterfalls, including the impressive North Falls and South Falls, with stops to walk behind the cascading water. Your guide will lead you confidently along moderate trails, sharing insights on the park’s geology and flora.
This small-group trip includes a delicious picnic lunch, making it as much about the culinary experience as the natural scenery. Visitors love the personalized attention and the chance to see lively waterfalls and ancient trees that are hundreds of years old. The tour is excellent for those with some hiking experience who want a comprehensive day outdoors.
Guests praise the professional guides and the breathtaking scenery, with one reviewer calling it “spectacular” and “marvelous.” The value for money is high, given the included lunch and expert guiding.
Bottom Line: If waterfalls and moderate hiking appeal to you, this all-day trip offers a full immersion into Oregon’s natural beauty.
5. Forest Park Hiking Tour to Pittock Mansion
Number 5 features the Forest Park Hiking Tour to Pittock Mansion, blending urban wilderness with historic grandeur. The tour starts at the Lower Macleay Trailhead and follows the Wildwood Trail, Oregon’s longest city-based trail, for about an hour. You’ll pass through majestic Douglas Firs and Western Hemlocks before reaching the Pittock Mansion for panoramic views of Portland and the surrounding mountains.
This tour is perfect for those wanting a manageable walk that combines nature with history. The guide shares stories about the park’s roots and the mansion’s architecture. Reviews highlight expert local guides and the easy pace, making it suitable for families or less experienced hikers.
The tour’s value is notable given the free access to the mansion grounds and the opportunity to enjoy some of the best city views in Portland. It’s a great option if you want a shorter, educational experience.
Bottom Line: A quick yet rich experience—ideal for visitors who want to combine light hiking with a touch of history.
6. Multnomah Falls and Columbia River Gorge Half-Day Hiking Tour
Ranking 6, the Multnomah Falls and Columbia River Gorge Half-Day Tour is a favorite, attracting over 1,600 reviews. This 4-hour outing focuses on the iconic Multnomah Falls, the highest waterfall in Oregon, with stops at Larch Mountain and other scenic viewpoints. It’s perfect for travelers short on time but eager to see one of the Pacific Northwest’s most famous sights.
The tour includes short hikes to vantage points, along with stories about the region’s geology and history. Guests love the comfortable van ride and the knowledgeable guides. For many, this is a must-do for the scenic waterfalls and easy access from Portland.
The value is high considering the admission included and the chance to see multiple waterfalls. It’s suitable for families, couples, or solo travelers looking for a balanced, scenic experience.
Bottom Line: Perfect for a half-day escape that delivers Oregon’s signature waterfalls with minimal hassle.
7. Moonlight Snowshoe Hike
Number 7 offers the Moonlight Snowshoe Hike, a rare chance to snowshoe under the full moon around Mount Hood. This 6-hour experience includes snowshoes, snacks, and hot cocoa while exploring the frosty woods after sunset. It’s designed to be accessible and memorable, with a guide showing you the ropes.
This tour is perfect for winter outdoor lovers seeking a unique experience with nighttime snowshoeing. The reviews mention Davin’s engaging guidance and the enchanting atmosphere of walking in a quiet, snow-covered landscape under the moonlight. Given the seasonal nature, this trip is best booked during winter months.
It’s a peaceful, atmospheric adventure suitable for those comfortable with snowshoeing and looking for something beyond the typical day hike. The experience is both relaxing and photo-worthy.
Bottom Line: An unforgettable winter outing, ideal for couples or solo adventurers wanting a magical night in Oregon’s snowy woods.
8. Full-day Columbia Gorge Hiking
At number 8, the Full-day Columbia Gorge Hiking offers an 8-hour small-group exploration of the Gorge’s many trails. This flexible tour can include rainforest hikes, fire-scarred slopes, or visits to historic sites like the Columbia Gorge Discovery Center. The itinerary is tailored to your interests, with lunch provided and admission to the museum included.
What sets this apart is the customizable nature—your guide adapts to your preferences and fitness level. Guests note the knowledgeable guides and the chance to visit less crowded areas. The tour is best suited for active travelers who want a comprehensive day of hiking and sightseeing.
While pricier, the personalized approach provides excellent value for those keen on a full immersion into the gorge’s diverse landscapes and history.
Bottom Line: If you prefer a private, adaptable adventure, this full-day tour is hard to beat.
9. Columbia River Gorge Full Day Private Tour and Hike
Number 9 offers a luxurious, private experience with the Columbia River Gorge Full Day Private Tour and Hike. Led by Master Naturalists, this tour is highly customizable, including stops at Bridal Veil Falls, Multnomah Falls, and even fruit farm visits depending on the season. The guide works with you to choose exactly the hikes and sights that suit your interests and fitness level.
Guests love the personalized attention and the depth of knowledge shared, with a focus on the region’s geology, flora, and fauna. The itinerary includes two or more stops, a delicious picnic lunch, and admission to attractions. The price reflects the premium experience and tailored approach.
This tour is perfect for discerning travelers who want an intimate, flexible day exploring Oregon’s iconic Gorge and lesser-known spots.
Bottom Line: For a bespoke, high-end experience with a naturalist guide, this private tour is unmatched.
10. Explore Columbia River Gorge Half-Day Small-Group Hiking Tour
Ranking 10, this Explore Columbia River Gorge Half-Day Tour offers a shorter, active taste of Gorge highlights. It features hikes in “waterfall alley” with stops at Elowah Falls and Shepperd’s Dell, perfect for travelers with limited time or seeking a quick yet scenic outing.
While reviews are mixed, many appreciate the attention to detail by guides like Sylvie, who customizes hikes based on group ability and timing. The tour includes multiple waterfall stops, giving a variety of views within just four hours. It’s well-suited for active travelers wanting a compact experience.
The cost-effective nature makes it appealing, especially for those who want a taste of Oregon’s waterfalls without a full-day commitment.
Bottom Line: An efficient, scenic short tour, fitting well into a busy schedule or as an introduction to the Gorge.
11. Tom Dick and Harry Snowshoe Hike
Finally, the Tom Dick and Harry Snowshoe Hike offers an 8-hour winter adventure. Perfect for snow lovers, this tour provides snowshoeing on Mount Hood’s slopes with all equipment included. The focus is on making snowshoeing accessible and fun, with guidance suitable for beginners and experienced alike.
While there are no reviews yet, the full-day format promises ample time to enjoy the winter landscape and capture memorable photos. If you’re visiting during winter months, this is a fantastic way to experience Oregon’s snowy wilderness.
Bottom Line: An excellent choice for winter travelers seeking a full day of snowshoeing in a scenic mountain setting, with all gear provided.
How to Choose the Right Hiking Tour in Portland
When selecting your ideal hike, consider your budget, fitness level, and interests. If you want a quick urban escape, the Forest Park Urban Hiking Tour offers a great introduction to Portland’s green spaces. For those craving the must-see waterfalls, the Silver Falls Waterfall Hiking Tour or the Multnomah Falls Half-Day Tour deliver unforgettable scenery.
Hunters of coastlines and forests will enjoy the Cannon Beach or Silver Falls options. For a private, tailored experience, the Full-Day Private Gorge Tour offers customization, perfect for couples or groups with specific interests.
Timing also matters: winter snowshoeing is best with Moonlight Snowshoe Hike, while spring and summer are perfect for waterfalls and coastal walks. Book early, especially for popular tours, to ensure your preferred date.
Final Thoughts
Portland offers a diverse range of guided hikes for various interests and fitness levels. For a quick taste of the city’s natural beauty, the Forest Park Urban Hiking Tour is unbeatable. Nature lovers seeking waterfalls will find Silver Falls and Multnomah Falls hard to beat, while coastal explorers will enjoy Cannon Beach.
For those wanting a more personalized experience, the private Columbia Gorge Tour provides the flexibility to tailor your day. Whether you prefer a short urban walk, a full-day waterfall trek, or a moonlit snowshoe, Portland’s outdoor tours promise memorable days in nature. Booking early is wise, especially during peak seasons, so you won’t miss out on your perfect adventure.