The 7 Best Drinking Tours in Portland
Portland’s reputation as a craft beer capital isn’t just a boast—it’s backed by a thriving scene of breweries, lively neighborhoods, and unique local stories. The city’s rich brewing culture makes it an ideal place for drinking tours that reveal its character, history, and eccentricity. Whether you’re into ghost stories, biking, or sampling local brews, Portland offers a variety of experiences that go beyond just tasting. These tours are perfect for travelers looking for authentic, memorable ways to explore Portland’s vibrant drinking culture.
From underground tunnels haunted by ghostly legends to bike rides past local breweries, this list covers a wide range of tours designed to suit different tastes and schedules. If you’re curious about Portland’s dark past or want to see the city from a bike saddle, there’s something here for you. Just remember to pace yourself and enjoy the local flavors and stories along the way.
Quick Overview
This list includes tours with historical themes like the Haunted Underground Shanghai Tunnel Tour with Brewery Tastings, active biking adventures such as the Portland Oregon Breweries By Bike and E-bike, and fun quirky pub crawls like the Weird Portland Pub Tour. There are options for those who want a shorter, focused experience or a full-day trip through Oregon’s craft scene, including private tours and haunted pub crawls. Each offers a unique way to experience Portland’s lively drinking culture and local stories.
1. Haunted Underground Shanghai Tunnel Tour with Brewery Tastings
At number 1, this tour combines Portland’s dark history with local beer. You’ll explore the Shanghai Tunnels—a network of underground passages once used for clandestine activities—on a small-group walking tour lasting about 90 minutes. Your guide will share stories of Portland’s shady past, including the role these tunnels played in transporting goods and, allegedly, people. You might even catch a glimpse of Nina, the resident ghost, if the stories are true.
After the walk, the tour offers three tastings and a full pint of award-winning Portland beer. The tour involves walking up and down stairs and maneuvering around pipes, so it’s not for those with mobility issues but perfect for history buffs and ghost story lovers. Guests consistently praise the tour’s rich storytelling and the authentic underground access that’s usually off-limits. Reviewers note guides like Natasha making the experience fun and spooky, with comments such as “Very informative about the history of the tunnels” and “Natasha was a blast.”
Bottom line: This tour offers a rare look at Portland’s underground past with a tasty beer reward. It’s ideal for history enthusiasts, ghost story aficionados, and anyone curious about Portland’s shadowy side.
2. Portland Oregon Breweries By Bike and E-bike
Number 2 on our list is the bike tour of Portland’s breweries, perfect for those who want to see the city actively while sampling its best beers. This roughly 3-hour tour takes you on a bike ride through Portland’s bike-friendly neighborhoods with stops at two top breweries, chosen from the tour guides’ favorites. Led by guides like Pierre or Delaney, you pedal past parks, rivers, and historic districts, gaining a true sense of Portland’s laid-back vibe.
The tour includes sample beers at each stop—with guests encouraged to share—and concludes back at the bike shop with a final beer and a souvenir pint glass. Guests consistently highlight how biking is a fun and efficient way to experience Portland’s craft beer scene and cityscape at the same time. Reviewers mention the casual pace and the knowledgeable guides, with one commenting, “Much more than expected on the ride, and I loved trying local beers.”
Bottom line: An excellent choice for active travelers who want to explore Portland’s biking infrastructure and brewpubs in one go. It offers a great mix of sightseeing and tasting for roughly $75.
3. Weird Bar Crawl with Fanatical Local
Number 3 is a casual walking tour that dives into Portland’s quirkiest neighborhood bars in East Portland. Led by an enthusiastic local guide, Dresden, this tour emphasizes interacting with locals and exploring the neighborhood vibe. You’ll visit favorites like coffee shops, pubs, and hidden spots, all while learning about Portland’s eccentric culture.
Included in the price is the first beer, and your guide will introduce you to local legends—think Bigfoot sightings or stories about Portland’s “keep Portland weird” motto. Guests rave about Dresden’s passion and local insights, with reviews mentioning “a fun night out” and “interesting conversations about Portland’s culture.” The tour lasts about three hours and is ideal for those who like socializing and discovering local hangouts away from the tourist crowds.
Bottom line: Perfect for travelers looking for a relaxed, social evening and authentic neighborhood experiences. It’s a great way to meet new people while exploring Portland’s quirky side.
4. Weird Portland Pub Tour
Next up, this tour immerses you in Portland’s eccentric pub scene, focusing on the Hawthorne and Division neighborhoods. Over about three hours, you’ll visit famous breweries and pubs, with stops at places like Baerlic Brewing and McMenamins Barley Mill Pub. Your guide will share legendary stories, including tales of exploding whales and Portland’s “keep it weird” ethos.
The tour includes free tastings at each location and time to order food if you wish. Guests appreciate the quirky atmosphere and the informative storytelling, with reviews noting the interesting legends and lively environment. The bars feature local art and famous murals, adding visual interest to your experience. Fans of Portland’s artsy, weird vibe will find this tour a highlight.
Bottom line: This tour combines Portland’s art, legends, and craft beer in a lively pub crawl, ideal for those wanting to see Portland’s creative spirit and learn local stories.
5. Portland Pubs Walking Beer Tour
Number 5 is a more upscale and detailed tasting experience in Portland’s historic beer scene. Over approximately 2.5 hours, you’ll visit three breweries—like Shipyard Brewing, Liquid Riot, and other favorites—by minibus, making it easier to cover more ground. The tour offers behind-the-scenes insights into the brewing process, combined with tastings and snacks.
Guests commend the personalized experience and guides like Jeff or Tom, who blend history, beer knowledge, and local tips seamlessly. Reviewers mention the variety of beers and the local legends they learned about, which enhances the tasting experience. The tour is well-suited for beer enthusiasts who want a rundown of Portland’s beer scene in a shorter time.
Bottom line: For those who prefer a more in-depth and structured beer tasting with transportation included, this tour delivers a rich, guided experience that highlights Portland’s craft beer excellence.
6. Private Back-Country Distillery, Brewery, or Pub Tour
At number 6, this private tour offers an 8-hour exploration of Oregon’s distilleries, breweries, and local farms. It’s designed for groups seeking a customized experience, traveling through the Willamette Valley with stops at seven different venues, including distilleries and local farms. The trip includes lunch at a butchery and deli and opportunities to taste craft spirits and brews.
Guests describe it as a curated journey perfect for men or women wanting to escape the city and experience regional flavors. The tour’s length and private nature mean it’s best suited for those who want an all-day, personalized adventure. The price of $290 reflects the comprehensive, exclusive nature of this experience, making it a good value for those looking for luxury, comfort, and variety in a day.
Bottom line: This is ideal for groups or couples seeking an ultimate Oregon tasting trip with custom stops and full-day luxury.
7. Portland Ghosts Boos and Booze Haunted Pub Crawl
Rounding out the list, this haunted pub crawl blends spirits and spirits—ghost stories and craft beers—over about two hours. You’ll visit Kells Irish Pub, the Shanghai Tunnel Bar, and other haunted hotspots. Your guide will tell spooky stories about Portland’s paranormal past as you pass notable sites like the Benson Hotel and the Shanghai Tunnels.
Guests love the mix of ghost tales and local pubs, with reviews noting guides like Lori being energetic and detailed. Drinks are not included, but the storytelling and atmosphere make this a fun, spooky option for history fans and adventurers. The tour is perfect if you want a shorter, entertaining evening with a paranormal twist.
Bottom line: This tour offers a light-hearted, spooky experience combining haunted tales with Portland’s drinking scene—great for those who enjoy ghost stories with a drink in hand.
How to Choose Your Perfect Portland Drinking Tour
When selecting among these options, consider your interests and schedule. If you’re fascinated by Portland’s underground and ghost stories, the Haunted Underground Shanghai Tunnel Tour offers a unique glimpse into the city’s shadowy past. For active explorers who want to see the city while enjoying local beers, the Portland Oregon Breweries By Bike and E-bike combines exercise with tastings.
Those seeking a more social, neighborhood experience should consider the Weird Bar Crawl or the Portland Pub Crawl. For more comprehensive beer education with transportation, the Portland Pubs Walking Beer Tour is a top pick. And if you want a luxury experience or private tour, the Back-Country Distillery, Brewery, or Pub Tour offers a curated day in Oregon’s wine country.
Booking early is advised, especially for popular tours during peak seasons. Think about your fitness level, time constraints, and whether you prefer history, active exploration, or just sampling—these details will help you pick the best fit.
Final Thoughts
Portland’s drinking scene is as varied as its neighborhoods. Whether you’re into spooky underground tunnels, biking past local breweries, or hanging out in quirky pubs, there’s an experience for every adventurous palate. The haunted tunnel tour and the bike brewery tour stand out for their unique mix of culture and activity, ideal for those craving something memorable. Meanwhile, the pub crawls and quirky pub tour bring Portland’s eccentric spirit alive.
Whatever your taste—whether ghostly legends, craft beer, or neighborhood vibes—these tours will give you a deeper appreciation of Portland’s authentic character. Be sure to check availability and book early, as these experiences tend to fill up fast during the busy seasons. Happy tasting!