Portland, Oregon, is a city that takes its craft beer seriously, but it also offers a fascinating mix of haunted history and quirky nightlife. Its compact downtown, historic districts, and bike-friendly streets make it a perfect place for drinking tours that blend local flavor with storytelling and adventure. Whether you’re into ghost stories, underground secrets, or hopping between breweries, Portland’s drinking scene is richer and more diverse than most. These tours stand out because they offer not just drinks but stories, history, and a chance to see the city in a different light.
If you’re looking for something memorable to do after a day of sightseeing or want to add a spooky twist to your visit, these three options deliver a little bit of everything—from haunted pubs to underground tunnels and bicycle brewery hops. Each offers a unique way to experience Portland’s local scene and its intriguing past.
1. Portland: Underground Shanghai Tunnel Tour with Beer Tasting
At number one on our list is the Portland: Underground Shanghai Tunnel Tour with Beer Tasting, which combines history, ghost stories, and craft beer—making it a fantastic choice for those curious about Portland’s shadowy past. For around $40 per person, this 1.5-hour tour takes you beneath the streets of Chinatown into the infamous tunnels, which once served as a route for smuggling and perhaps darker deeds.
What sets this tour apart is the chance to walk in the footsteps of sailors and shadowy figures, hearing tales of Portland’s seedy underground and its resident ghost. The guide’s storytelling is engaging and detailed, with many visitors praising guides like Natasha and Kaitlyn for their entertaining narration and knowledge. The tour concludes at Old Town Pizza with a full pint of Portland craft beer, which is served either inside the tunnels or at a historic spot above ground. This unique mix of history, paranormal tales, and beer tasting makes it ideal for those interested in Portland’s mysterious side with a laid-back vibe.
Guests consistently mention the lively guides and atmospheric setting, making this tour a fun, slightly creepy experience that’s also educational. If you like stories of ghosts and secret passages combined with a beer, this tour hits the mark.
Bottom Line: A perfect pick for history buffs and ghost lovers who want a relaxed, immersive experience with a good beer in hand.
2. Portland: Ghosts Boos and Booze Haunted Pub Crawl
The Ghosts Boos and Booze Haunted Pub Crawl offers a 2-hour journey through downtown Portland’s most haunted bars and pubs, all while sharing stories of the city’s darker side. For just $30, this tour invites you to sip your favorite drink as your guide recounts tales of pirates, murders, and secret government plots that are woven into the fabric of Portland’s night spots.
What makes this tour stand out is its focus on local haunted sites like Kelly’s Olympian, where spirits are said to linger. The guide Victoria Rose gets high praise for her storytelling and engaging style. Tour participants often enjoy the private rooms and the chance to experience the ambiance of each haunted location while listening to spine-tingling stories. An added fun feature is the EMF reader, which adds a playful paranormal element to the evening.
This tour is best suited for those who enjoy urban legends, spooky stories, and a lively bar scene. It’s a relaxed, social experience with enough thrills to keep you interested without feeling overly intense.
Bottom Line: An affordable and spirited way to explore Portland’s haunted bars with a lively group and a good dose of storytelling.
3. Portland: Guided Bike Tour with Brewery Visits
For those who prefer a more active approach, the Portland: Guided Bike Tour with Brewery Visits provides a scenic way to sample Portland’s craft beer scene. With a 3-hour route and a price of $65 per person, this tour is perfect for active travelers who want to combine sightseeing with beer. It takes you through historic East Side neighborhoods, across iconic bridges like the Blumenauer Bicycle and Pedestrian Bridge, and visits multiple breweries, including Migration Brewing and Rogue Eastside Pub.
What makes this tour special is the blend of cycling and beer tasting, giving you a chance to see Portland’s neighborhoods up close while enjoying fresh, locally brewed beers. The itinerary includes stops at well-loved venues and scenic spots like Tom McCall Waterfront Park and Laurelhurst Park, with plenty of time at each brewery to relax and chat.
Guests have commented on the well-organized route and the chance to get a behind-the-scenes look at Portland’s craft beer industry. The tour is best suited for fit travelers who want a mix of activity and beer, but it can be a bit rushed if you prefer more time at each stop.
Bottom Line: A great choice if you want to combine exercise, sightseeing, and beer sampling all in one tour.
How to Choose the Right Drinking Tour in Portland
When deciding between these options, consider your interests and activity level. If you’re fascinated by Portland’s underground past and ghost stories, the Shanghai Tunnel Tour offers an atmospheric experience with beer included. For those who love urban legends and spooky storytelling but prefer a more social vibe, the Haunted Pub Crawl is a budget-friendly choice with plenty of local character. If you’re an active traveler who enjoys cycling and sampling craft brews, the Bike and Brewery Tour combines exercise with beer tasting amid Portland’s scenic neighborhoods.
Consider your fitness level, your budget, and whether you’re more interested in history, ghost stories, or active exploration. Booking early is recommended, especially in peak seasons, to secure your spot.
Final Thoughts
Portland offers a wide range of drinking tours that cater to different interests and energy levels. For a mix of ghost stories and underground secrets with a craft beer finale, the Shanghai Tunnel Tour is hard to beat. If you prefer a spooky but relaxed pub crawl through haunted bars, the Haunted Pub Crawl provides a lively, story-filled evening. And if you want to combine physical activity with brewery visits, the Bike and Brewery Tour delivers a scenic, energetic adventure.
Each tour provides a memorable way to experience Portland’s local character—whether that’s through stories of spirits, underground mysteries, or hops. Booking your preferred tour early ensures you won’t miss out on these unique adventures. Whatever your style, Portland’s drinking tours promise a fun, engaging way to see the city from a different perspective.