Top Portland Seasonal & Special Occasions - page 2

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 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.

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.

Discover Portland's darker side on an adults-only haunted pub crawl through the city's historic Old Town district. Visit legendary bars, haunted landmarks, and infamous locations connected to Portland's most chilling ghost stories, true crime mysteries, and the notorious Shanghai Tunnels. Along the way, hear tales of restless spirits at Kells Irish Pub, the ghostly residents of the Benson Hotel, the unsolved murder connected to the Roseland Theater, and the tragic legend that still haunts Old Town Pizza & Brewing. Between stops, enjoy time at local pubs while exploring the history of sailors, bootleggers, performers, laborers, and outcasts who helped shape Portland's haunted reputation. Perfect for paranormal enthusiasts, history buffs, and anyone looking for a unique night out, this 21+ experience combines haunted history, local legends, and Portland's vibrant bar scene for an unforgettable evening after dark. All guests must be age 21+ and have a valid I.D. with them.

Get out of the big city and explore the stunning beaches and beautiful towns along Oregon’s northern coast on this full-day, small-group tour from Portland. Visit the charming towns of Manzanita and Cannon Beach—home of the famous Haystack Rock—browse antique shops and art galleries, and stop at several beaches to maximize your time at the Oregon Coast.

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.

Portland takes pizza seriously—and this tour is the easiest, most fun way to taste the scene in one walk. You’ll hit four pizzerias on a relaxed route with short walks in between (about ~1 mile total), tasting a curated progression of styles and signatures. This is a full-meal experience: each guest gets a full slice at each stop (four slices total). Your guide keeps it laid-back and social while sharing quick, useful pizza insight—what makes a great slice, what to order, and where to go next depending on what you loved most. Pizza and drinks are included. Rain or shine, come hungry and ready to eat like a local.

The Oregon coast is one of the most majestic geologic formations that was formed by lava flows millions of years ago. We depart to the coast and have lunch in the charming town of Cannon Beach and do hiking and exploring on the coast. Explore the majestic Oregon coast, view the amazing Haystack Rock formation, and during low tide gaze at starfish and clams. We will also explore Oswald State Park for lite trail walking and see the stunning cliffs of Manzanita point. This is a joinable small group tour for 2 persons or more, door to door service. Please dress for the season, expect a full day beginning 10am and back to Portland by 6pm.

Step aboard Portland’s only tiki boat for a ~2 hour river cruise that blends laid-back island vibes with playful onboard energy and scenic city views. This experience shifts naturally with the crowd. Relax and take in downtown landmarks and iconic bridges, sip a drink, and enjoy the breeze as we cruise the Willamette. A lively onboard host keeps the atmosphere fun, offering various games such as trivia, cornhole and chances to win prizes for those who enjoy a bit of friendly competition! Whether you're here to unwind, connect with family, meet new friends, or rediscover the city from the water, this cruise is designed to flow with the moment. It's a perfect mix of chill hangout, social outing, and river adventure, all with an unforgettable Island Style.

Experience the Willamette Valley, Oregon's largest wine region, on this wine-tasting tour from Portland. In a small group, head south of Portland to the Willamette Valley wine region, famed for its Pinot Noir. Spend the day tasting different wines (at your own expense) at three select wineries and learn about the region, and Oregon’s wine industry, from your guide.

Explore the eerie side of Old Town with this haunted pub tour in Portland. Learn about some of the city's scary history as you walk through 19th-century buildings. Sample local beers as you hear about Portland's era of kidnapping, gangs, prostitution and opium dens.

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.

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.

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.

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

Wine-lovers rejoice, this one’s for you! Enjoy a full year of wine-tasting experiences and exclusive discounts on purchases from more than 450 wineries across the United States’ renowned wine-making regions. With convenient access to a concierge service that helps you get the best value out of the priority pass, your year of wine-tasting and vineyard tours is as easy as raising a glass.

Want to learn how to grill like a professional and the art behind good barbecue? Learn from an instructor who's trained in France, Spain, Argentina, South Korea, and more with this small-group cooking class in Portland, Oregon. Get hands-on practice and guidance with recipes that combine traditional Southern techniques and global flavors.

The perfect sanctuary for men to escape the toils of daily life, fill their gullets with fine crafted spirits and brews, and beat their chests in harmonious praise and triumph of a day’s hunting well done! Embark on a meticulously curated journey spanning 7 hours, traversing through the rugged beauty of the Willamette Valley while experiencing some of the most badass distilleries and breweries in the region. And fear not, for this invitation extends to sassy or wild women alike! These are not pearl district hipster lounges, but rather, some of the most unique destinations to grab a beer or whiskey in the Willamette Valley; artisans that are off the beaten path, have small batch mentalities, or farm the ingredients that go directly into their craft. Your adventure awaits with a trifecta of brewery or distillery visits, curated to your desired experience, and transportation in one of our spacious and upfitted vehicles. Take a photo/video tour of our fleet online and book your adventure!

Winery hop through the Willamette Valley, known for its Pinots, with this small-group tour. You will visit three different tasting rooms where you’ll get the chance to sample wine safely, without having to worry about driving. You’ll also stop for lunch along the way, included in the price of the tour.

Your day may include stops at iconic destinations such as Multnomah Falls, Horsetail Falls, or the Fruit Loop (depending on the fruit season), while also leaving time to hike on the trails and away from crowds. Alternatively, your group may choose a longer day hike such as Angel’s Rest with a gorgeous view of the Columbia River below, or Multnomah Falls and Wahkeena Falls wandering through a lush old growth forest. At Good Trip Adventures, our expert guides are not just knowledgeable; they are passionate about Columbia River Gorge. From the geological wonders to the unique flora and fauna, they ensure you develop a deeper connection with this mesmerizing landscape. Groups are capped at 8 hikers. If we don't meet the minimum number of spots booked, registrants will be offered an option to make the tour private for an additional charge or cancel for a full refund.

Explore Portland's hipster-friendly Buckman neighborhood on foot and try out some fantastic local fare along the way with this small-group walking tour. While dining options vary depending on availability, you're likely to visit some of Portland's top international restaurants, try out treats from a food pod, and spend time at a local distillery, all with a guide to provide context and narration.

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

Once we have secured your date, you will be in touch with your personal host for the day. We will provide a complementary itinerary or a complementary consultation of an already prepared itinerary. Your host will not only be an expert guide, but your guide will have worked every aspect of wine production and the front of house experience. Our hosts are all CPR certified. We pride ourselves in introducing our guests to boutique wineries, less than 8,000 cases of wine produced in a given year. Let us introduce you to world class wine you won't find on most shelves around the world.

We’re definitely Keeping It Weird on the Underground Donut Tour - Portland Holiday Edition. Come join us as we take a stroll through downtown Portland and try some of the best donuts you'll ever have in your life. Seriously, these donuts are amazing. The tour starts near the PSU campus where we try an assortment of donuts. Next, we take a leisurely walk through the park towards downtown Portland. Along the way you'll learn about Portland history, both for donuts as well as the larger restaurant industry. Depending on what's open that day, we may stop at one of several donut shops downtown, so make sure to bring your appetite. We'll stop along the way to admire the holiday lights and decorations, specifically in Pioneer Square. Lastly, we'll stop at the place that started it all, Voodoo Doughnuts. Don't worry though, because we can skip the line. Along the way, we'll sprinkle in some humor, history, and fun for the whole family. What's not to love? We hope you can make it!