Top Portland Holidays

Beneath Portland's vibrant streets lies a darker story. Join The Dark Below and explore the city's most chilling legends, notorious crimes, and haunted landmarks. Journey through historic Old Town and Chinatown as your guide uncovers tales of Shanghaiing, underground tunnels, tragic deaths, unsolved mysteries, and the restless spirits said to linger where Portland's darkest history unfolded. Visit iconic locations including the Shanghai Tunnel district, Old Town Pizza & Brewing, the Roseland Theater, Kells Irish Pub, and the waterfront where kidnapped sailors were once forced aboard ships bound for distant ports. Along the way, discover stories of vice, disappearances, and paranormal encounters that helped shape Portland's haunted reputation. Combining authentic local history, true crime, and ghost lore, The Dark Below offers an unforgettable journey into the shadows of one of the Pacific Northwest's most haunted cities. Guests must be at least 16 years old to participate.

Discover the history and legends behind Portland’s Shanghai Tunnels on a small-group walking tour. Follow your guide beneath a restaurant to the tunnels, which once connected local businesses and hotels to the Willamette River. Learn about subterranean historic events and perhaps catch a glimpse of Nina, the resident ghost. Afterwards, resurface and enjoy three tastings and a full pint of locally produced beer.

Combine a fun night out with ghostly tales of the city during this Portland Haunted History Pub Crawl Experience. This pub crawl takes you to multiple pubs, including Kells Irish Restaurant and Pub and Shanghai Tunnel Bar as you pass by city highlights such as the Benson Hotel. Hear spooky stories of ghosts and paranormal activity from your guide during the evening.

Skip the dry history tours and lean into Portland's more eccentric side on this pub tour in the Hawthorne and Division neighborhoods. Combine beer with art as you try local brews and visit the area's most famous murals. Learn about local legends, from Bigfoot sightings to exploding whales, that you wouldn't discover on your own.

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

Experience a unique spa treatment that combines Oregon wine, self-care, and relaxation at the only vinotherapy spa in the United States.

Taste your way through Oregon’s renowned wine scene right in the heart of Portland! Try a variety of wine varietals and savor delicious bites, all while exploring the vibrant Pearl and Slabtown neighborhoods. What makes this wine tour special? We’ve met with the wine experts themselves and did all the research for you, so the tastings and snacks are curated and included. You’ll try 10+ wines at two winery tasting rooms plus one wine bar, including a variety of white, rosé, and red, and snack small bite pairings. Highlights: - Taste 4 Oregon wines paired with artisan popcorn at an approachable winery while learning why Oregon wine is special. - Explore 2 trendy Portland neighborhoods, blending old and modern architecture with rich history. - Dine on bruschetta paired with wine at a family-run winery. - End your evening sipping Bordeaux in a secret wine bar where you might just uncover a hidden surprise. - Learn from your tour guide and wine experts. *This tour is 21+ ONLY.

Visit Mt. Hood and the Columbia Gorge, with a couple of stops for wine tasting along the way, with this full-day tour. You'll visit Multnomah Falls, the Columbia Gorge's most famous attraction, hang out at Mt. Hood's historic Timberline Lodge, and pay a visit to two different wineries to taste Gorge-produced wine. There will be a hosted lunch on tour and a glass of wine at one of the wineries included. You will also be able to purchase beverages at your leisure during winery visits.

The Northern Willamette Valley's close proximity to Portland creates a perfect opportunity to join others on a small group public tour of Oregon’s wine country with Sea to Summit Tours, Portland Oregon's original tour and adventure company. Experienced, knowledgeable guides, providing fun and informative tours with unparalleled customer service, while operating the nicest and most comfortable, custom equipped 4x4 Mercedes-Benz vehicles in Portland’s tour industry. We set an itinerary with outstanding wine, great hospitality, and beautiful scenery with wine tasting fees included – all the keys to creating a unforgettable Willamette Valley Wine Tour for our clients... Created, owned and operated by native Portland Oregonian's, since 2001

Our Sips & Sights Tasting Cruises pair local wine tasting with a 2-hour sightseeing and social cruise on the Willamette River! Featured wineries: • Oct 4: Love & Squalor • Oct 11: Hip Chicks Do Wine • Oct 25: Stoller Family Estate Your ticket includes: • 2 hours cruising time • Three 1-oz wine tastings from the featured winery host • One full glass of select wine from our onboard bar • Charcuterie snack • Hawaiian lei + grand prize raffle entry • Onboard game, prize + Portland sightseeing tidbits Hear from the featured winery while enjoying Portland's bridges, city views and river scenery. Our onboard bar is also open for additional purchases. All ages welcome. Alcohol is for guests 21+ with valid ID. Sail, sip & see Portland in Island Style!

From fiery deaths to watery graves: In this 1.5 mile cemetery walking tour, we weave what we know of the peoples who lived here for millennia with verifiable stories of recent centuries. We can only guess, based on our psychics’ readings and eerie coincidences we have observed, where people here before us feared to walk and canoe at night. As a wise person wrote, every story ends as a ghost story. Our ghosts are legion. We now call it Oregon; “ourigan” was ancestral home to hundreds of thousands. They have left a darkness here, expressed with stories from the earliest days of our written history to modern times. Starting with early disasters, we will tell ghost stories we have collected, from fiery deaths to those in the waters of nearby river; from self-inflicted to deaths brought by the state or a rich man’s guilt. Our route takes us through the inner eastside, where more of Portland’s disasters have happened than any other part of the city & where many early settlers are buried.

Sample three of The Rose City's craft breweries, and learn Portland architecture and history, as you walk through the Pearl, Old Town, and West End districts. Taste the entire range of beer types, in the city that consistently ranks in the top three for number of breweries.

Explore Oregon's world famous wine country known as the Willamette Valley and experience the best Pinot Noir, Pinot Gris, Rose, Chardonnay and other varietals guided by local wine lovers with an opportunity to do food pairings at a vineyard or seperate lunch stop. Gain an inside perspective about the growing region, the winemaking process and the history of this valley at each vineyard during your tasting. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. This is limited to 10 people in a small joinable group, but usually much smaller in our modern and comfortable 15 passenger vans.

Discover Oregon's world famous wine region known as Willamette Valley and experience the best pinot noir, chardonnay, rose and other varietals guided by local wine lovers on this 8 hour tour. An excellent trip for new and seasoned wine lovers, a romantic weekend, or last minute vacation with your friends. Gain an inside perspective about the growing region, the winemaking process and the history of this valley. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. This is a joinable small group tour for 2 persons or more. We will explore 3 of the finest vineyards in the valley and do a sit down lunch at our favorite establishment or vineyard lunch pairing. Proceed to check availability to see your exact price for the group size, we will handle all route planning and reservations on your behalf and offer door to door pickup and dropoff.

Explore Portland's vibrant nightlife on a two-hour guided bike tour, where laughter and good vibes flow alongside refreshing drinks. The Classic Crawl takes you through the city's coolest neighborhoods and stops at three local bars, showcasing everything from neon-lit dives to quirky favorites. Perfect for groups looking to celebrate special occasions or simply enjoy a fun night out, this tour features onboard music and group photos to capture the memories. Come ready to pedal and dress up for the occasion—costumes are encouraged. - A public tour means making new friends, allowing others to join you on your crawl. - Two-hour guided bike tour through Portland's neighborhoods. - Visit three unique bars and enjoy a lively atmosphere. - Group photos and music provided for a memorable experience. - Minimum group size of 6 and maximum of 15 riders.

Go bar hopping with a local resident with this casual, friendly walking tour of Portland's local bars. Your enthusiastic local guide will take you and your group to some of his favorite local haunts, with a heavy focus on interacting with locals and checking out the city's neighborhood vibes.

Oregon's Willamette Valley is known for its Pinots and it's a fantastic place to go wine tasting, provided you leave the driving to someone else. This private tour will take you to three wineries, where you'll sample wine and learn about the ins and outs of Pinot production. You'll be able to sample safely, knowing that someone else will be doing the driving.

The Columbia Gorge NSA features waterfalls, mountains, monoliths, terraces, resort towns, vineyards, orchards, and The River, harboring a plethora of fish and birds, and unique plants and invertebrates. In the early 1900s, Portlanders would drive their Model T cars along the Columbia River Highway to gaze at waterfalls. There is said to be over 4000 waterfalls; many are hidden away, but many are just a short hike off the Historic Highway. On this afternoon half-day tour you'll make new friends while exploring "waterfall alley", including views of the Vista House and a stop at Multnomah Falls, the tallest waterfall in Oregon and most visited site in the Pacific Northwest. Your expert guide will teach you about the natural history, cultural history, and wine background of the area, as you drive the Historic Columbia River Highway Scenic Byway. You'll continue on to stop at a vineyard in the Columbia Gorge American Viticultural Area (AVA). Tasting fees included.

Visit the top attractions in the Columbia River Gorge National Scenic Area and Mt. Hood National Forest on this day trip from Portland. After spending the morning chasing waterfalls and marveling at 500-pound fish at Bonneville Fish Hatchery, enjoy free time for lunch in historic downtown Hood River. After lunch, we will visit a vineyard in the region for a wine tasting and drive more than halfway up the side of Mt. Hood to explore Timberline Lodge

Oregon’s Willamette Valley is known for its fantastic wine, and while it’s easy to get to from Portland by car, driving yourself means limiting your consumption. This small-group tours includes the services of a driver so you can taste wine without worrying about designating a driver, showcasing off-the-beaten-path wineries that you might otherwise miss.

This is an amazing way to see the most spectacular Oregon wonders like Multnomah Falls, Vista Point driving thru the breathtaking and rugged beauty of the Columbia Gorge. We will see various waterfalls like Multnomah Falls, Latourell Falls , a lunch stop in the quaint historic downtown Hood River, a wine tasting stop at one of the amazing Vineyards in the Columbia Gorge AVA. This is ideal if you want to do some scenic, nature stops with light trail walking and also enjoy a vineyard stop, its absolutely the most amazing way to spend 8 hours.

Chef Sarah brings a cozy, down-to-earth vibe to this pasta-making class in Portland, making it easy for anyone to dive in and have fun with no experience needed. You’ll learn real pasta techniques in a relaxed, hands-on setting as you mix and knead fresh egg-free dough using simple ingredients like flour, water and salt. While your dough rests, you’ll work as a group with a prepared batch to practice rolling and cutting pasta with a machine. Then, Chef Sarah will show you approachable hand-shaping techniques that prove fresh pasta does not require special equipment. As you shape your dough, she’ll demonstrate how to make a rich butter sage sauce with garlic, lemon and olive oil, then cook the fresh noodles you cut together. At the end of class, you’ll sample the pasta made during the session and take home a full batch of fresh pasta to cook within the next three days.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.