Oregon Hiking - Bend, Crater Lake and the Cascades - Lodge Based

Trip Length4 Days
Group Size4-11
Activity level
Starting from
$2,799for REI Members
$3,079 for non-members
DeparturesJul 2025-Sep 2025

Experience four unforgettable days hiking and paddling based in Oregon’s adventure capital, Bend. Enjoy the breathtaking landscapes of the Cascade Mountains and Crater Lake National Park by day and Bend’s downtown charm by night.

Rugged mountain peaks and tranquil alpine lakes create the perfect playground for lovers of the outdoors. This carefully curated itinerary takes you through some of Oregon’s most iconic and beloved destinations, from lush old-growth forests west of the Cascade crest to the high desert cliffs of Smith Rock. With opportunities to hike volcanic summits, paddle pristine waters, and explore the vibrant craft beer culture of Bend, it’s no wonder this region captures (and keeps!) so many hearts.

Your exploration begins with a rewarding climb offering sweeping views of the Cascade Range. We paddle the crystal-clear waters of the Cascade Lakes Region, followed by time to explore Bend’s lively downtown. We travel to magnificent Crater Lake National Park, where the collapsed caldera of ancient Mount Mazama meets the surreal blue depths of the deepest lake in the U.S. We round out our adventure with a visit to the colorful Smith Rock State Park, where we hike amidst dramatic rock formations. As we wind our way through the golden basalt and tuff cliffs and walk along the Crooked River, our guides share the unique and fascinating natural history and geology of the special places we travel through. Each day showcases a different facet of Oregon’s beauty, inviting you to savor and immerse yourself in its diverse natural wonders.

 Our days are filled with invigorating hikes, fascinating geology and historical insights with the spectacular Cascade Range as our backdrop.

Trip Highlights

  • Hike to awe-inspiring viewpoints overlooking Crater Lake, the deepest lake in the U.S.
  • Explore the high desert’s unique ecosystem and geologic history with expert guides
  • Kayak across a pristine alpine lake offering breathtaking views of the Cascades
  • Discover the dramatic rock formations of Smith Rock State Park
  • Unwind in your cozy hotel, nestled in downtown Bend

Activities

This trip is rated Moderate [3]. Trip members should be capable of hiking with a daypack for up to 9 miles with elevation gains/losses of up to 2,200'. Our hikes take place between 3,000’ and 8,000’ in elevation. Trails are composed of packed dirt, large and/or loose rocks, with some steep sections and exposed overlooks. Trip members should have prior hiking experience and be in good physical condition, able to hike 4 to 6 hours a day for four consecutive days. The kayak excursion is suitable for beginners.

  • Kayaking
  • Hiking

What's Included

Guide leadership; 3 nights of accommodations; transportation during the trip; meals as noted in the daily itinerary; all permits and entrance fees; tandem kayaks (singles are not available) and related equipment; see gear list for details on equipment provided.

Accommodations

Hotel, 3 nights

Your Adventure Itinerary

Itinerary map for Oregon Hiking - Bend, Crater Lake and the Cascades - Lodge Based
Day 1

Welcome to Bend! Set out on a hike with stunning Cascades vistas

Our guides warmly welcome you and your fellow adventurers in downtown Bend, OR. After introductions and a quick overview, we take a scenic shuttle, soaking in the views as we make our way to the trailhead of our first hike. From here, we dive into our adventure, immersing ourselves in the region’s stunning beauty as we tackle a steep ascent. Our hike takes us through old-growth forests and colorful meadows, slowly unveiling breathtaking views of the Cascade Range. As we climb, the trail offers glimpses of Mount Washington and the Three Sisters. Upon reaching the rocky summit, we’re treated to 360-degree views of the surrounding peaks and valleys, a truly rewarding start to our adventure. After our hike, we check in to our hotel in charming downtown Bend to unwind before enjoying a delicious dinner at a local favorite brewpub. Lunch and dinner included. 

Hiking: 7-8 miles; Total ascent/Total descent: up to 2,200’; Low point/High point: 3,658’/5,737’; Van transfer: 2.5 hours 

Day 2

Paddle across a shimmering alpine lake and explore downtown Bend

After breakfast, we shuttle along the Cascade Lakes Scenic Byway to explore one of Oregon’s vibrant alpine lakes by kayak. We glide through crystal-clear waters, surrounded by towering pines and the striking Cascade peaks. The crisp mountain air and serene atmosphere invite us to appreciate the rich biodiversity of the region. As we paddle, we keep an eye out for eagles, great blue herons, and beavers that inhabit this remarkable landscape. Our guides share their extensive knowledge, adding depth to our understanding of this unique ecosystem. After our paddle, choose between hiking up Pilot Butte with our guides for panoramic views of Bend and the distant Cascade Range, or head downtown to discover Bend’s eclectic boutiques, craft breweries, and cozy cafes. The day wraps up with a mouthwatering dinner at a beloved local restaurant, where we savor Pacific Northwest flavors and recount the day’s adventures in good company. All meals included. 

Paddling: 4-hour tour; Hiking: 1.5 miles, Total ascent/Total descent: +/-450’; Low point/High point: up to 3,670’/4,136’; Van transfer: 1.5 hours 

Day 3

Bask in the sublime panoramas of Crater Lake National Park

We kick off the day early to make the most of every moment. After a scenic two-hour drive, we arrive at Crater Lake National Park, where we explore the breathtaking landscapes surrounding the deepest lake in the U.S. As we follow the trail, we encounter magnificent vistas around every bend—giant pines, the dreamlike blue waters of the lake, and the rugged rim formed by ancient volcanic activity. Our expert guides share insights into the park’s fascinating volcanic history and the unique geologic formations shaped by past eruptions. We marvel at the remnants of the Mount Mazama caldera, a testament to the powerful forces that created this incredible terrain over 7,700 years ago. Along the way, our guides seamlessly intertwine the rich natural history of the area with its cultural significance, highlighting the stories of the indigenous peoples who have long revered this sacred site. The trail’s varied terrain reveals dramatic contrasts, from rocky cliffs to lush, forested areas. We pause for lunch with views of the lake, soaking in the tranquil beauty. Tonight, we gather for a special farewell dinner at the historic Crater Lake Lodge Dining Room before our return journey back to Bend. All meals included.  

Hiking: up to 9 miles; Total ascent/Total descent: up to 2,200’; Low point/High point: up to 7,027’/8,008’; Van transfer: 4 hours 

Day 4

Explore Smith Rock before saying farewell to fabulous Bend

This morning, we set off for Smith Rock State Park, a 650-acre gem renowned for its dramatic rock formations and rich climbing history. Our trail takes us along the Misery Ridge Loop, a 4-mile circuit that ascends steeply, unveiling spectacular views of towering basalt cliffs overlooking the meandering Crooked River below. As we hike up the rugged ridges, we traverse the very crags where sport climbing in the United States took its first bold steps, with legend Alan Watts leaving his indelible mark here in the 1980s. Our guides share fascinating insights into the park’s geology and the evolution of climbing at this iconic destination. After our hike, enjoy some leisure time exploring and relaxing in the park before we head back to downtown Bend and bid farewell to our fellow adventurers. Breakfast and lunch included. 

Hiking: 4 miles, Total ascent/Total descent: 900’; Low point/High point: up to 2,634,’/3,300’; Transfer: 1.5 hours 

Itinerary map for Oregon Hiking - Bend, Crater Lake and the Cascades - Lodge Based

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

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We provide

What to pack

Contact Us

Feel free to give us a call at 1 (800) 622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales ( 1 (800) 426-4840 ) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.

Trip specifics may change over time. Reviews reflect the version of the trip that was active at the time the reviewer took it. Please review the itinerary as described above and call our team for any additional details.