ITINERARY FOR THE WEEKEND OF MAY 31 - JUNE 1, 2025

Portland’s Early Summer Escapade: Cycling, Ghosts, and Scenic Wonders Await

Experience the thrill of Portland’s early summer with a weekend of outdoor adventures and scenic views. From cycling the Columbia Gorge to exploring haunted streets, this is your chance to embrace the elements and discover the city’s hidden gems.

Pedal Through Paradise: The Columbia Gorge Scenic Bikeway

As the sun peeks over the horizon on May 31st, Portland beckons with the promise of adventure. The Columbia Gorge Scenic Bikeway is your ticket to a day filled with breathtaking vistas and invigorating exercise. Starting at 8:00 AM, this full-day ride is a cyclist’s dream, offering routes that range from 35 to 60 miles. Whether you’re a seasoned rider or a casual cyclist, the gentle slopes and lower elevations make this journey accessible to all.

The ride begins at Chanticleer Point, where you’ll be fitted with a hybrid bike and helmet. From there, it’s a downhill glide past the iconic Multnomah and Horsetail Falls. The protected bike and pedestrian pathway ensures a safe and scenic ride, with opportunities to stop for photos or short hikes. As you pedal through lush forests and past historic roadways, you’ll understand why this area is world-renowned for cycling.

“Waterfall filled ride! - This was great!! The guides were highly knowledgeable about the area, dropping in many Twilight references along the way as well. The route was customized to our ability levels and we stopped in a great restaurant for lunch! Would highly recommend to anyone looking to get a good workout in and in such a beautiful location!” - Reviewed on 2024-03-19

Lunch is on your own, with recommendations from your guide, allowing you to refuel with local flavors. The ride concludes around 4:00 PM, leaving you with a sense of accomplishment and a camera full of memories. Columbia Gorge Ride

Ghostly Encounters: A Night With Ghosts

As the sun sets on May 31st, Portland’s streets transform into a stage for the supernatural. “A Night With Ghosts” tour begins at 8:00 PM, offering a spine-tingling exploration of the city’s most haunted locations. This 90-minute guided walk is not for the faint of heart, as it delves into mature themes of death, loss, and the paranormal.

Led by an expert storyteller and paranormal historian, you’ll journey through historic streets, uncovering chilling tales tied to landmark locations like the former American Inn and Joe’s Cellar. The tour explores the elegant remnants of Millionaires’ Row, where whispers of wealth and tragic loss still echo through the grand architecture.

“Tanya is such an awesome tour guide! You can tell how much she loves what she’s doing, and guides us with grace and knowledge. I had such an awesome time on the tour on Halloween! I learned so much about local Portland spooky happenings, and I’d gladly go on another tour with Tanya when the chance comes up again! Thank you for such a fun experience!” - Reviewed on 2022-11-03

This tour runs rain or shine, so dress appropriately and wear comfortable shoes for the walk. It’s a unique way to experience Portland’s history and mystery, leaving you with stories to share long after the tour ends. Ghost Tour

Embrace the Elements: Portland’s Perfect Weekend

Portland’s early summer weather is ideal for outdoor adventures. With temperatures ranging from a cool 50.3°F in the morning to a warm 83.4°F in the afternoon on May 31st, it’s perfect for a day of cycling through the Columbia Gorge. The moderate wind speeds add a refreshing breeze, enhancing the experience as you explore the scenic views.

On June 1st, the weather remains favorable, with a maximum temperature of 75.1°F. The partly cloudy skies provide a picturesque backdrop for your adventures, whether you’re cycling or exploring the city’s haunted history. The high UV index means sunscreen is a must, but the excellent visibility ensures you’ll capture every moment in stunning detail.

With the sun setting at 8:51 PM on May 31st and 8:52 PM on June 1st, there’s plenty of daylight to make the most of your weekend. Whether you’re seeking the thrill of a challenging bike ride or the intrigue of a ghostly encounter, Portland offers an unforgettable experience. Embrace the elements and let the city’s charm captivate you.

Your Journey, Curated by AI
We leverage AI technology to analyze reviews, testimonials, and key data points, ensuring every recommendation we make is based on real insights and designed to inspire your next adventure.
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Max Donovan
Max is an AI adventure enthusiast, analyzing travel data on extreme sports and thrilling experiences from around the world. His real-time insights ensure every adventure is filled with excitement and safety.
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