Portland’s reputation as a craft beer capital is well-earned, but the city’s drinking scene offers much more than just pints. Its mix of historic spots, quirky neighborhoods, and underground secrets makes it a lively place for any type of drinker. Whether you’re into ghost stories, cycling from brewery to brewery, or exploring Portland’s oddball side, there’s a tour for you. We love the Haunted Underground Shanghai Tunnel Tour (see details) for its blend of Portland’s dark past and local brews, and the Weird Bar Crawl (see details) for its fun exploration of neighborhoods filled with murals and legends. These tours show Portland’s spirit—quirky, historic, and full of character.
Portland is a city that loves its beer, its stories, and its oddities, making it a perfect destination for a variety of drinking tours. Our favorites include immersive experiences like ghost pubs and underground tunnels, as well as active outings such as bike tours. Whatever your style, you’ll find plenty of ways to explore Portland’s lively drinking scene.
Quick Overview
Our list includes underground tunnel tours, bike brewery adventures, haunted pub crawls, and quirky neighborhood bar hops. All tours are carefully selected for their unique appeal, reviews, and value. For example, the Haunted Underground Shanghai Tunnel Tour with Brewery Tastings (see here) offers exclusive access to Portland’s underground history combined with local beer tastings. Meanwhile, the Portland Oregon Breweries By Bike and E-bike (see here) blends exercise and exploration through Portland’s famous beer scene. Below, you’ll find detailed insights into each tour, helping you decide which fits your interests and travel style.
1. Haunted Underground Shanghai Tunnel Tour with Brewery Tastings
At number 1, this tour combines Portland’s shadowy Shanghai Tunnels with beer tastings, creating a blend of history and fun. The 90-minute underground tour takes you beneath a restaurant into tunnels that once connected hotels and businesses to the Willamette River. Your guide shares stories of Portland’s dark past, including the infamous human trafficking and illicit activities. You might also catch a glimpse of Nina, the resident ghost, making it a spooky yet fascinating experience. After the tour, enjoy three tastings and a full pint of award-winning local beer. It’s a perfect mix of history, ghost stories, and craft beer.
What makes this tour stand out is exclusive access to the tunnels and the storytelling that weaves ghosts and history together. The walking involves stairs and maneuvering pipes, which could be tricky for those with mobility issues. Tour reviewers praise the knowledgeable guides and the spooky atmosphere. If you love a mix of history and a little thrill, this is a top pick.
Bottom Line: An engaging, spooky tour that offers a genuine glimpse into Portland’s underground past combined with excellent local brews.
2. Portland Oregon Breweries By Bike and E-bike
For around $75, this bike tour lets you pedal through Portland’s bike-friendly streets to visit two carefully chosen breweries. The 3-hour journey is designed for those who want to combine active exploration with beer tasting. Your guide takes you to favorites from a curated list, and you can sample beers at each stop (own expense). The ride is leisurely, with opportunities to enjoy Portland’s neighborhoods, parks, and riverside views. Finish back at the bike shop with a final microbrew and a souvenir pint glass.
This tour is great for active travelers who want to see Portland from a different perspective. Tour reviews emphasize the friendliness of guides like Pierre and Delaney, as well as the opportunity to learn about Portland’s craft scene while enjoying a casual ride. It’s perfect for those who prefer a bit of exercise with their beer.
Bottom Line: A fun, laid-back way to explore Portland’s beer culture with the added perk of scenic riding — ideal for active, social travelers.
3. Haunted Pub Tour
Number 3 on our list is the Haunted Pub Tour, a two-and-a-half-hour walk through Old Town Portland’s historic pubs. This tour combines local craft beers with spooky stories about ghosts haunting buildings and streets from the 19th century. You’ll stop at iconic pubs like the Merchant Hotel, long reputed to be haunted, and hear tales of kidnapping, gangs, and opium dens. Six craft beers are included, giving you a taste of Portland’s best brews while you soak in the eerie atmosphere.
The tour is praised for guides like Madison, who makes the stories come alive with enthusiasm. The walk involves some standing and strolling through historic streets, making it suitable for most fitness levels. If you’re intrigued by ghost stories and Portland’s darker side, this tour offers a well-balanced mix of drinks and tales.
Bottom Line: A fun, spooky walk through Portland’s haunted pubs, perfect for those who enjoy a mix of history, spirits, and ghostly legends.
4. Weird Bar Crawl with Fanatical Local
At number 4, this 3-hour walking tour explores Portland’s Eastside neighborhoods, known for their quirky bars and street art. Led by a passionate local guide, you’ll visit favorites like Baerlic Brewing, Lucky Labrador, and McMenamins. The tour focuses on Portland’s “weird” culture, sharing legends from Bigfoot to exploding whales, along with recommendations for other offbeat spots. The first beer is included, and the guide encourages interaction with locals and fellow travelers.
Reviews highlight Dresden’s enthusiasm and the lively conversations about Portland’s oddities. It’s especially suited for travelers who enjoy neighborhood vibe, street art, and local legends. The tour offers a relaxed pace with plenty of opportunities to chat and explore.
Bottom Line: A lively, casual exploration of Portland’s quirky neighborhoods and bars, ideal for those wanting an authentic local experience.
5. Bar Harbor and Acadia Full Day Private Tour from Portland
This private tour takes you from Portland to Maine’s stunning coast in style. With a personal driver and guide, you’ll visit Fort Knox with its impressive bridge views, explore Acadia National Park’s mountains and shoreline, and enjoy two hours in the charming town of Bar Harbor. The tour includes stops at Stephen King’s house for fans of the author and plenty of scenic photo opportunities. It’s a flexible, comfortable way to see Maine’s highlights at your own pace.
Reviewers love AJ’s knowledge and personable approach, and the private setting is perfect for families or groups seeking custom experiences. The tour lasts roughly 6-8 hours, so it’s best for travelers with full days to spare. While not a traditional drinking tour, it’s perfect for those wanting a scenic escape with some local flavor.
Bottom Line: A premium, flexible way to see Maine’s coast and mountains with personalized service — great for lovers of scenery and literature.
6. Weird Portland Pub Tour
Number 6 offers a 3-hour adventure into Portland’s more eccentric side, focusing on pubs in the Hawthorne and Division neighborhoods. The tour combines local brews with stories about Portland’s weird legends, like Bigfoot sightings and legendary whales. The stops include Baerlic Brewing, Lucky Labrador, and McMenamins, with plenty of time for drinks and conversation. Your guide shares offbeat facts and points out murals and art along the way.
Reviewers note the tour’s quirky charm, with guides like Otniel creating a lively atmosphere. It’s perfect for those who want to combine beer tasting with Portland’s unusual stories. The tour is moderate in pace and includes a free first beer.
Bottom Line: A fun, quirky pub crawl that mixes local legends with Portland’s eclectic bar scene—ideal for curious and open-minded travelers.
7. Portland Pubs Walking Beer Tour
Number 7 is a small-group walking tour focusing on three of Portland’s top breweries. Over 2.5 hours, you’ll visit Shipyard Brewing, a major Maine brewery, and learn about the brewing process. You’ll also explore the city’s neighborhoods, including the Pearl and Old Town, while sampling beers and enjoying snacks. The tour emphasizes local culture, with visits to historic sites and favorite brewpubs.
Guests enjoy the personalized experience, with guides sharing insights about Portland’s beer scene and architecture. The walking involves some terrain but is manageable for most. It’s best suited for beer lovers who want an intimate look at Portland’s brewing culture.
Bottom Line: A well-rounded tour for beer enthusiasts looking for an in-depth, small-group experience in Portland’s vibrant neighborhoods.
8. Private Back-Country Distillery, Brewery, or Pub Tour
This exclusive 8-hour tour is for those who really want to indulge. It includes visits to multiple distilleries and breweries in Oregon’s Willamette Valley, along with a stop at a local butchery and deli for lunch. The journey covers Dundee, Newberg, and Dundee, tasting some of the region’s best craft spirits and brews. It’s a curated experience for serious enthusiasts seeking a full day of sampling and sightseeing.
Reviewers see it as a “badass” experience, especially suited for those who love spirits, food, and scenic drives. The tour is pricey but offers a luxurious, all-inclusive day. It’s best for groups celebrating or connoisseurs eager to explore Oregon’s top craft producers.
Bottom Line: An all-in, premium craft beverage experience in Oregon’s wine country — perfect for dedicated fans of spirits and craft brewing.
9. Portland Ghosts Boos and Booze Haunted Pub Crawl
Number 9 offers a 2-hour tour combining ghost stories with visits to haunted pubs. Walking through Old Chinatown and stopping at bars like Kells Irish Pub and Shanghai Tunnel Bar, you’ll hear about Portland’s haunted spots and paranormal activity. The tour includes stops at several pubs, passing by landmarks like the Benson Hotel. It’s ideal for those interested in Portland’s spooky side with a drink in hand.
Reviews mention the guide Houston’s storytelling and the relaxed pace. Drinks are not included, but the atmosphere makes up for it. It’s suitable for groups who enjoy a bit of fright and fun in one evening.
Bottom Line: A lively ghost-themed pub crawl perfect for fans of paranormal tales and Portland’s haunted corners.
How to Choose Your Perfect Portland Drinking Tour
Choosing between these diverse options depends on your interests, fitness level, and how deep you want to go into Portland’s drinking scene. If you love history and ghosts, the Haunted Underground Shanghai Tunnel Tour is a unique experience. For active explorers, the Bike Brewery Tour offers a scenic ride with plenty of tastings. Those craving Portland’s quirky side will enjoy the Weird Bar Crawl, which combines murals, legends, and local bars.
If you prefer intimate, personalized experiences, the Portland Pubs Walking Beer Tour delivers a deep dive into the city’s craft beer culture. For serious connoisseurs, the Back-Country Distillery and Brewery Tour offers a full day of tasting Oregon’s best in scenic settings.
Booking early is wise, especially in summer or during peak weekends, as these tours tend to fill up quickly. Consider your preferred pace, whether walking, biking, or relaxing, and pick the experience that best matches your style.
Final Thoughts
Portland’s drinking scene is as eclectic as the city itself, offering something for all—from ghost stories and underground tunnels to bike adventures and quirky pub crawls. If you’re interested in history and spirits, the underground tour is a must. For active explorers, the bike brewery tour combines fun and fitness. And if you enjoy local legends and offbeat neighborhoods, the weird pub crawl will hit the spot.
No matter what you choose, these tours make it easy to experience Portland’s vibrant, diverse drinking culture. Be sure to book in advance, and don’t forget to pace yourself—Portland’s many breweries are eager to welcome you. Cheers to discovering Portland’s best sips and stories!