Portland’s 14 Best Drinking Tours: Which To Choose?

Portland is famous for its innovative brewing scene, quirky bars, and a love for all things unique. It’s a city where craft beer isn’t just a drink but a way of life, and history mixes with a dash of the weird.

We especially like tours that combine local storytelling with authentic experiences, like the Haunted Underground Shanghai Tunnel Tour, which offers a glimpse into Portland’s dark past alongside refreshing beer tastings.

Plus, the Weird Bar Crawl with Fanatical Local captures Portland’s eccentric spirit, making it perfect for travelers eager to explore local neighborhoods with a guide who knows the best spots.

If you’re after something educational and lively, a bike brewery tour like the Portland Oregon Breweries By Bike and E-bike offers a fun way to cover more ground while sampling Portland’s best microbrews. For those interested in spooky stories and historic pubs, the Haunted Pub Tour brings Portland’s haunted tales to life with visits to the most haunted buildings and lively storytelling.

Whatever your style, Portland offers a variety of drinking tours that can satisfy your curiosity, taste buds, and sense of adventure.

1. Haunted Underground Shanghai Tunnel Tour with Brewery Tastings

At number 1 on our list, the Haunted Underground Shanghai Tunnel Tour combines history, legend, and beer in a compact 90-minute experience. You’ll go beneath a local restaurant to explore Portland’s famous Shanghai Tunnels, which once connected hotels, warehouses, and the Willamette River for illicit activities.

Your guide shares stories of Portland’s darker days and the resident ghost Nina, making the experience both eerie and educational.

The tour finishes with three beer tastings and a full pint of award-winning local beer, making it a perfect blend of history and craft.

Reviews highlight the tour’s engaging storytelling and exclusive access to the tunnels, with Natasha praised for her genuine research.

The price of $40 per person makes it a valuable option for those interested in Portland’s mysterious past plus a bit of local flavor.

Bottom Line: Ideal for history buffs and ghost enthusiasts who enjoy a craft beer finish. It’s a short, engaging tour with plenty of atmosphere and a good dose of Portland’s underground lore.

2. Portland Oregon Breweries By Bike and E-bike

At number 2, the Portland Oregon Breweries By Bike and E-bike offers a lively, active way to explore Portland’s thriving craft beer scene. Over roughly three hours, you’ll pedal between two top microbreweries favored by the local guides—meaning you’ll get to see parts of the city that are less touristy.

The tour includes sample beers at each stop (at your expense) and ends back at the bike shop with a souvenir pint glass and one last beer. The guides are highly rated, and the casual pace makes it accessible for most fitness levels.

With a perfect 5-star rating from reviews, this trip is especially good for adventurous drinkers who want to enjoy Portland’s vibrant neighborhoods on two wheels.

Bottom Line: Best suited for active travelers who want to combine cycling with craft beer tasting. It’s a fun, social tour that offers a true taste of local Portland.

3. Haunted Pub Tour

Number 3, the Haunted Pub Tour, is a 2.5-hour walk through Portland’s Old Town, focusing on local haunted pubs and their ghostly legends. This tour visits historic sites such as the Merchant Hotel, where stories of paranormal activity are intertwined with Portland’s notorious past—including stories of opium dens and gangsters.

You’ll sample six craft beers from award-winning Portland breweries while hearing ghost stories about 19th-century buildings that still seem to whisper.

Guests praise the knowledgeable guides and the perfect mix of spooky tales and local beer. The $45 price point offers a good value considering the length, drinks, and storytelling.

Bottom Line: For those who enjoy history with a haunted twist, this tour blends Portland’s dark past with lively pub stops, making it a memorable evening.

4. Weird Bar Crawl with Fanatical Local

The Weird Bar Crawl with Fanatical Local, at number 4, is a 3-hour walk through Portland’s quirkiest neighborhoods, like Hawthorne and Division. The tour kicks off at Baerlic Brewing, known for award-winning beers and a fun Northwest vibe.

You’ll visit several local favorites, hear stories about Portland’s legendary Bigfoot sightings and explosive whales, and explore murals and art that celebrate the city’s “Keep Portland Weird” mantra.

Your first beer is included, and the guide, Dresden, is lauded for making the experience lively and informative. It’s a relaxed, social way to discover Portland’s eccentric character.

Bottom Line: Perfect for travelers seeking an authentic local vibe with quirky stories and good beer, especially if you like to explore neighborhoods on foot.

5. Bar Harbor and Acadia Full Day Private Tour from Portland

Number 5 offers a luxurious escape into Maine’s scenic coast with a Private Tour to Bar Harbor and Acadia. In 6 to 8 hours, you’ll visit Fort Knox, admire the coastal vistas of Acadia National Park, and wander the charming streets of Bar Harbor. This is a customized experience perfect for travelers who want flexibility and comfort.

The tour is led by a professional guide in an air-conditioned vehicle, with bottled water included. Reviews praise the guide’s knowledge and the ability to adapt to weather changes.

While not primarily a drinking experience, it’s a top choice for nature lovers wanting a scenic day trip from Portland.

Bottom Line: Ideal for travelers seeking a scenic, flexible day exploring Maine’s coast, with options for optional local food and drinks in Bar Harbor.

6. Weird Portland Pub Tour

Number 6, the Weird Portland Pub Tour, is a 3-hour jaunt through Portland’s Hawthorne and Division neighborhoods. It’s a lively exploration of art, murals, and local legends like Bigfoot.

Starting at Baerlic Brewing, the tour visits quirky breweries and pubs, each with its own story, artifacts, and atmosphere. The guide shares offbeat Portland stories, including local legends that aren’t on any tourist map.

You’ll get a taste of Portland’s “keep Portland weird” culture, with the first beer included in the price. The reviews note the fun, quirky vibe and the interesting stories.

Bottom Line: Best for travelers who want a laid-back, quirky night that combines local art, legends, and craft brews.

7. Portland Pubs Walking Beer Tour

Number 7, the Portland Pubs Walking Beer Tour, is a 2.5-hour experience exploring three of Portland’s best breweries in a small-group setting. You’ll visit Shipyard Brewing, one of Maine’s largest breweries, plus a newer brewery and a traditional brewpub. The tour includes behind-the-scenes insights into beer-making and multiple tastings, with snacks to complement the drinks.

With a cost of $102 per person, it’s a bit pricier but offers an intimate, personalized experience. The reviews highlight the expert guidance and the chance to go off the tourist trail.

Bottom Line: Suited for beer enthusiasts who want an up-close look at Portland’s beer scene with expert insights.

8. Private Back-Country Distillery, Brewery, or Pub Tour

Number 8 is a full-day private tour ($290 per person) that takes you through Willamette Valley’s most exclusive distilleries and breweries. Perfect for groups wanting a personalized experience, you’ll visit seven stops, including an aerial view at Wilsonville and hidden distilleries in Dundee and Newberg.

The tour involves carefully curated stops, tasting premium spirits and craft brews, with some stops including local food pairings.

It’s best suited for serious connoisseurs or groups celebrating a special occasion. The reviews mention the expert curation and customized experience.

Bottom Line: Ideal for serious drink aficionados and groups wanting a luxury, personalized day of tasting.

9. Portland Ghosts Boos and Booze Haunted Pub Crawl

Number 9 offers a 2-hour haunted pub crawl exploring Portland’s most haunted pubs and buildings. You’ll pass through iconic spots like Kells Irish Pub and the Shanghai Tunnel Bar, with stories of ghostly activity and paranormal mysteries. Drinks are not included, but the tour offers lively storytelling and a fun atmosphere for those interested in Portland’s spooky side.

The reviews mention the engaging guide and the enjoyable mix of history and ghost stories. It’s perfect for night owls and supernatural fans.

Bottom Line: For a lighthearted, spooky night with some local drinks and lots of stories, this tour is a fun choice.

10. Portland’s Best Barbecue, Brewery, and Distillery Van Tour

Number 10 is a culinary-focused tour, combining craft beer, barbecue, and spirits. It features stops at Orange Bike Brewing, Noble Pizzeria & Barbecue, and Three of Strong Spirits. Over about 3.5 hours, you’ll enjoy tastings, good food, and lively conversation.

This tour is perfect for food lovers who want to indulge in Portland’s bold flavors. Since reviews are not available, we note the value in the variety of stops and the focus on local culinary highlights.

Bottom Line: Best for food and drink lovers with a hearty appetite looking to experience Portland’s culinary scene.

11. Craft Beer and City Walking Tour of Portland West Side

Number 11 offers a 3-hour walk through Portland’s West End, Pearl, and Old Town, visiting three breweries including Deschutes Portland Public House. You’ll also explore historic architecture and neighborhood hotspots while tasting local beers. The tour includes insights into the city’s history and culture, making it a great choice for travelers interested in both drinks and architecture.

While reviews are pending, the combination of urban exploration and tastings makes it appealing for history buffs and beer fans alike.

Bottom Line: For those who want to combine city sights with beer tastings, this tour provides a balanced experience.

12. Fun Pasta Making Class at a Local Brewery in Portland

Number 12 is a hands-on pasta-making class at a Portland brewery, led by Chef Sarah. Over 2 hours, learn real pasta techniques, enjoy the aroma of brown butter and sage, and share a relaxed, social experience.

Perfect for foodies or anyone wanting a creative night out, this class ends with delicious food and local brews. Although it’s not a drinking tour per se, it offers a unique culinary experience you won’t forget.

Bottom Line: Best for travelers looking for a fun, interactive activity that combines cooking with Portland’s beer culture.

13. Portland Axe Throwing and Two Local Breweries Van Tour

Number 13 combines adventure and drinks over a 3.5-hour tour. You start with a guided tasting at a local brewery, then try your hand at axe throwing — no experience needed. Afterward, you visit a second brewery to enjoy more local craft beers.

It’s an energetic way to combine physical activity with local flavors. Reviews are not available yet, but the combination of adventure and beers makes it appealing for thrill-seekers.

Bottom Line: For those who want a dynamic experience with learning new skills and tasting Portland’s best brews.

14. Fun Sushi Making Class at a Local Brewery in Portland

Number 14 offers a relaxed, hands-on sushi class led by Chef Sarah. Over 2 hours, you’ll learn simple sushi techniques, enjoy the aroma of fresh ingredients, and share in a casual, friendly atmosphere. The class concludes with delicious sushi and local brews, making it a great culinary break from typical pub crawling. It’s perfect for food lovers wanting a creative, engaging activity.

Bottom Line: Best for foodies who want to learn sushi skills while enjoying Portland’s craft beer scene.

How to Choose the Right Drinking Tour in Portland

When selecting the perfect drinking experience, consider your interests and schedule. If you love history and ghost stories, the Haunted Underground Tunnel Tour or Haunted Pub Tour might be your best bet.

For active explorers, the Bicycle Brewery Tour offers a fun and healthy way to taste local beers. If quirky Portland is your vibe, Weird Bar Crawl and Weird Portland Pub Tour deliver plenty of laughs and odd stories.

For a more relaxed, personalized experience, consider the Private Back-Country Tour, perfect for groups or connoisseurs.

Matching your tour choice to your interest in history, activity level, or culinary curiosity will ensure your Portland visit is memorable and satisfying. Booking early is recommended, especially for popular tours like the Bar Harbor and Acadia Tour, which fill up quickly.

To sum it up, Portland’s drinking tour scene offers everything from ghostly underground adventures to boisterous pub crawls and scenic coastal explorations. Whether you prefer learning about the city’s dark past, biking through lively neighborhoods, or sampling Maine’s finest brews, there’s something for every traveler.

For adventurers and history lovers, the Haunted Underground Shanghai Tunnel Tour provides a compelling mix of stories and sips. Meanwhile, those seeking fun and quirky local flavor will love the Weird Bar Crawl.

Whatever your style, booking these tours in advance will help you enjoy Portland’s rich drinking culture to the fullest.