Things to Do in
Portland OR

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor. This is The Real Portland Tour! Check my website for a complete listing of tour days, times, and availability.

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stories largely left out of the history books. Get ready to broaden your sense of what Portland and Maine have been and could be. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, we'll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. We’ll see where Indigenous Wabanaki leaders made their earliest relationships with European colonizers and walk together through the centuries. Enjoy an inclusive, empowering, and surprising constellation of tales that offers a welcome contrast to the more obvious themes you’re likely to experience on other tours. You'll enjoy 2 hours of narration over a 1.5-mile route with owner and guide, Dugan Murphy. He is Portland's top-rated guide on TripAdvisor!

Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s earliest settlements couldn’t have existed without Black labor, skill, and insight. You'll meet the Black Yankees who founded Maine communities, overturned slavery statewide, drove our maritime industries, gained political influence, crossed color boundaries, and expanded Mainers’ rights in the modern era. Stepping on granite cobblestones crooked with age — that once saw footfalls from national heroes like Frederick Douglass — you’ll pass storefronts once home to Black-owned barbershops where abolitionists whispered intelligence to Underground Railroad conductors. Enjoy 2 hours of entertaining and enlightening historical narration over a 1.5-mile route. Owner and guide, Dugan Murphy, dug through the archives to present an amazing constellation of stories left out of most tours. TripAdvisor named him Portland's #1 guide!

The High Cascades Scenic Tour will take you on an incredible up-close journey through the Cascade Mountains. This is the only ATV Tour in Oregon packed with beautiful views, lava tube caves, Lava Fields, Alpine Lakes, Volcanic Black Sand Dunes, and some of Central Oregon best trails.

Come experience some Northwest hospitality combined with amazing wines, all from the comfort of your personal helicopter.  We will whisk you away for roughly 6 hours, so please plan accordingly for your sublime escape.  Prior to departure, you will enjoy a delectable snack and a glass of Champagne, followed by a scenic flight to your first winery. Once there, you can expect to enjoy award winning wines and service, before being asked to re-board your helicopter en route to the next wineries. Expect a delightful new encounter and a delicious lunch. This is undoubtedly Pinot Noir country, but you won’t just taste reds. We worked hard to hand pick wineries that feature a rich variety of wines that have to be tasted in order to describe how wonderful they are. After you’ve touched down back where it all began, we invite you to stop and take some photos to help you remember your Tour Devine by Heli!

Standing majestically over the city, Mt Hood is the most prominent peak in the Oregon cascades. A popular destination for hiking, camping, and climbing, the glaciers atop Mt. Hood provide the only year-round lift-served skiing in North America, from the beautiful Timberline Lodge. Oregon Tour Co. offers a full day trip to the mountain, which includes the beautiful Hood River Valley, as well as the breathtaking waterfalls of the Columbia River Gorge.

Our 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.

Gone are the days of choosing between a drowsy shuttle bus driver or the self-proclaimed expert viticulturalist to guide your journey through Oregon wine country. Welcome to The Good Vibes Tour, we specialize in transporting you directly to the experts: the passionate artisans behind these exceptional Willamette Valley vintages. It all begins with The Vibe. Our drivers are adept at gauging the group and seamlessly adapting their interaction to enhance the collective; interacting as much or as little as adds to your experience. Then there’s our meticulously crafted luxury coaches. Far from your typical passenger van or conventional limousine, our transport evokes the ambiance of the Pacific NW; complete with an open and inviting floorplan, rustic wood accents, a simulated fireplace, and modern amenities like a coffee nook, Bluetooth music and optional karaoke. Take a photo/video tour of our fleet online and book your adventure!

This Full-Day Deschutes River adventure is a perfect trips the entire family, friends or couples can enjoy. From beautiful canyon scenery to challenging and trilling rapids, warm temps and easy access, this is a fantastic trip. Gather your crew and come spend a wonderful on the river.

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset. We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline. This experience is perfect for families and small groups, offering a completely private and personalized tour just for you. First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!

We’ve been running this trip for decades and we’re excited to show you why it’s so amazing. Soak up the whitewater and high-desert scenery on this 5.5 hour trip full of class III and IV rapids. . We have a 5-person minimum for our full day trip. We do combine smaller groups. Minimum age requirement for full day trips is 6 years old and at least 45 lbs.

When weighing the options for a unique adventure, family friendly experience, or looking for a must do adventure, this should be at the top of your list. No experience necessary, but you must be 8 years or older. For the first hour we will get equipped, practice, and learn how to use the equipment to climb giant trees. Then we will take off on a short hike before climbing some of the tallest trees in the world. Around 200-300 feet high into the canopy of rare giant old-growth trees and experience an adventure that seems to take you out of this world. This is your chance to do a new and unique eco-tour activity, less than .01% of the population has yet to do! During the intro tree climb you will learn the basic skills of recreational tree climbing and rappelling, as you move your way high into the upper canopy with gorgeous views of ancient forest and wildlife. This experience is like nothing you have never experienced before.

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB boat is suited to tour the region while everyone gets a front-row seat so you can see and experience more of it. Learn about Portland’s nautical history, view wildlife like seals, harbor porpoises, and sea birds, and stop for photos at quintessential sights like all four lighthouses, Fort Gorges, seals, and the working waterfront while also escaping to lesser-known areas of the bay where wildlife viewing is the best. This is a unique tour that is unmatched in the breadth of its experience with a local captain to guide you and answer your questions about the region. Please join us for the Best Of Casco Bay!

Gravel riding has taken the cycling world by storm. Prepare yourself for an urban forest adventure within the city. Ride from our shop in Old Town through the bustling Pearl District & Nob Hill as your guide highlights historical and cultural hotspots. Leave the city behind as you pedal into America’s largest urban forest – Forest Park. Carved into the slopes of the West Hills, cruise the stunning car-free gravel path which traverses the entire park and offers a scenic half-day trip all within city limits. The 11 mile bike and pedestrian path through the 5000 acre park is enshrouded with towering trees. Catch glimpses of the city below as you zip through the temperate forest. Return the way you came or head over the St Johns Bridge into North Portland for amazing views of the West Hills and the Willamette River from Overlook. 28 miles - This tour appeals to fit beginner and experienced gravel riders on our Carbon Gravel Bikes as well as new adventurers on our Gravel E-bikes.

Do you want to taste the best wines in Willamette Valley? Our custom private tours are designed to take couples and groups of friends deep into the heart of Willamette Valley to explore the cult wines, highest-rated wines, and legendary vineyards of Willamette Valley! We love building unique tours according to your preferences and ensuring you leave Oregon wine country with lasting memories. Our tours will take you to 3 or 4 wineries (depending on your desire for a slower pace or more experiences) and will include elevated tours if you choose. This private tour isn't simply about providing a driver, but ushering you into the best experience of Willamette Valley wines and wineries possible. McMinnville, Salem, Newberg, Dundee, and other pickup locations are all serviceable.

Do you want to taste the best wines in Willamette Valley? Our custom private tours are designed to take couples and groups of friends deep into the heart of Willamette Valley to explore the cult wines, highest-rated wines, and legendary vineyards of Willamette Valley! We love building unique tours according to your preferences and ensuring you leave Oregon wine country with lasting memories. Our tours will take you to 3 or 4 wineries (depending on your desire for a slower pace or more experiences) and will include elevated tours if you choose. Our wine tour company, Wine History Tours, is centered in the heart of the valley, and our primary drivers are all industry insiders with years of experience and connections. This private tour isn't simply about providing a driver, but ushering you into the best experience of Willamette Valley wines and wineries possible. McMinnville, Salem, Newberg, Dundee, and other pickup locations are all serviceable.

Explore Oregon's wine country on a guided private tour where you will visit small production wineries and sometimes even interact with owners and winemakers at the cellar door. Learn about how wine is made and get a new appreciation for what goes into making world class wine. After visiting four wineries over the course of the day you will never look at Oregon wine the same way again. It is truly a unique wine tasting experience!

There is no better way to discover the Columbia River Gorge, a must-visit destination when you're in Portland, than on a private tour just for you or with a companion. From stunning waterfalls to iconic viewpoints, this is your chance to experience the Pacific Northwest at its finest. Book your tour today and let the magic of Multnomah Falls and the Gorge’s natural wonders captivate you!

HEY. Do you want to see Portland through the eyes of its BIGGEST FAN? Are you curious about communities that prioritize PEOPLE, IMAGINATION, and CRAFT BEERS? Are you ready to embark on an ALL YOU CAN PORTLAND BUFFET through a walking tour featuring LOCAL HOTSPOTS and COOL STORIES? Then I’ve got the adventure for you: THIS TOUR. This walking tour explores where the locals go for Portland's nightlife! I show you the soul of the city by immersing you in its neighborhood culture. This means checking out a neighborhood district, drinking taps from neighborhood breweries, and getting the neighborhood perspective by interacting with someone who lives here! People who find this tour meaningful: 1. People who prefer a Drink, Eat, Drink night rather than a Drink, Drink, Drink night. 2. People who prefer to explore with welcoming friends rather than alone. 3. People who enjoy open-minded discussions and appreciate collecting new perspectives. LET'S GET WEIRD.

Escape games are unique and interactive live-action adventure experiences in which players like you and your friends, family or coworkers, become active participants in our immersive stories, and must work as a team to solve a multitude of intriguing problems and discover the final clue to “escape” before time runs out! Escape Ashland's games are designed for Ashland residents and visitors alike with the help of local artisans, electrical engineers and contractors, and we have become the go-to activity for visiting families, school groups and those seeking a memorable way to celebrate a special occasions. Our games, “The Scottish Play” and “The Ramblin Rogue Saloon,” are light-hearted, accessible to all and success focused. Our exceptional game hosts ensure that each group leaves feeling challenged and connected in an unforgettable way.

Portland River Tours delivers a premier river experience through carefully curated routes featuring iconic landmarks such as the Steel Bridge and the White Stag now the Portland Oregon neon sign, paired with engaging commentary on the city’s history, architecture, and culture. Enjoy our spacious, well-appointed boats designed for comfort, supported by eco-conscious operations and a strong commitment to exceptional service. Choose a premium private charter for up to six guests for an intimate luxury experience, or join a shared cruise with up to 18 passengers—offered daily—for a vibrant and social outing on Portland’s scenic waterways.

Guided full-day Oregon Coast tour with a local guide and driver. Includes transportation between tour stops, scenic viewpoints, photo stops, coastal stories, movie locations, and local history. Pickup and drop-off in the Astoria or Seaside area may be available. This immersive 7-hour tour explores Astoria, Warrenton, Gearhart, Seaside, and Cannon Beach. Planned stops may include Fort Stevens, South Jetty, the Peter Iredale Shipwreck, Fort Clatsop, Astoria’s waterfront, scenic viewpoints, and Haystack Rock, when tides allow. Guests will enjoy approximately one hour of free time in Seaside to explore, shop, walk the Prom, or purchase lunch on their own. Highlights: small-group tour, Fort Clatsop, Fort Stevens, South Jetty, Peter Iredale Shipwreck, Haystack Rock, Astoria history, movie locations, and coastal viewpoints.

Willamette Valley is world-class wine country — but the best way to taste it is with someone who can tell you why it matters. On this private, fully customizable tour, your guide brings 10+ years of wine-industry experience, pairing standout Oregon Pinot with the stories of how wine has shaped Western culture. It's for people who love a great glass and a great story in equal measure. We keep it small and unhurried — no big buses, no rigid script. Just your group, a comfortable luxury vehicle, and a hand-picked route through the boutique, family-owned wineries at the heart of the valley: three at a relaxed pace, or four if you want to cover more ground. We'll even stop where the locals go for the kind of sandwich people plan road trips around. Round-trip pickup from your hotel or Airbnb is included. Lunch and winery tasting fees aren't, so you're free to choose what you eat and pour. Come tour the valley in style — relaxing, delicious, and quietly fascinating.

Experience the Oregon Coast beyond the typical tourist stops on this relaxed small-group tour through Seaside, Cannon Beach, scenic overlooks, hidden coves, movie sites, and coastal communities. Hear local stories, learn about regional history and marine life, and discover places many visitors miss while your guide handles the driving, parking, timing, and hidden gems along the way. Every tour is flexible, curiosity-driven, and shaped by the coast itself.

Private Casco Bay Cruise – Up to 5 Guests Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline. Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.

The Rogue River thrill seeker is the trip for the group who can’t decide on the experience they want so they choose to do it all. In the morning paddle yourself in an inflatable kayak through the pristine pools in the bottom of Hellgate Canyon. Take on some adventure and paddle yourself through the class II rapids of the Rogue River in your own inflatable kayak! Our guides will teach you the skills and show you the lines, but paddling through will be all you, and you can certainly do it! Mid-day the group will enjoy lunch on our patio between games of ladder golf. After you have had your fill we load in the van for a short drive to the put-in for the Nugget Falls section of the Rogue River. This section of the river has much bigger whitewater so we load into a paddle raft where you paddle as part of a team through the frothing torrents. The afternoon section builds in difficulty, culminating in the famous Tilomikh falls, a combination of two drops plummeting over 10 feet in total.

Come breakfast with us! Delve into three of Portland’s most acclaimed drinks and morsels. On this two hour tour you will experience Portland's coffee culture, our iconic artisanal donuts, and deliciously crafted chocolates. The perfect way to start any vacation in the Rose City. Our guides will share with you Portland's history in the third wave coffee movement, while leading you on a 1.5 mile walk through Portland's downtown. Embrace fantastic donut creations in entirely new flavor combinations as you learn about the origins of the donut and how it became a Stumptown staple. Finally we will visit chocolate makers, were we will learn more about chocolate varietals and their unique flavor profiles. Dietary restrictions: we CAN provide substitutions for vegetarians, non-alcohol guests, vegan, gluten free, or dairy allergies. All allergies and dietary restrictions must be indicated in advance at time of ticket purchase.

The Must-Do Sebago Lake Experience! Explore the panoramic views of Sebago Lake with our unbeatable rental package! With our EZ Launch system, you'll enjoy easy access to launch right from our private site nestled between Panther Run stream and the north end of Sebago Lake. With your fitted life jacket, paddle and map in hand, you'll have endless opportunities to discover the lake's hidden coves, beaches, islands and wildlife. Paddle along meandering streams before emerging into Sebago's scenic waters. Beach your vessel and savor a picnic lunch. Venture deep into secluded inlets to glimpse native wildlife. Or simply cruise the lake while soaking in Maine's iconic scenery. The varied landscape offers towering pines, rocky outcroppings and sandy beaches. Ample parking, friendly staff, and convenient amenities like bathrooms and changing rooms, our facilities make Sebago Lake an ideal destination for a hassle-free day on the water.

Let’s have fun strolling the delightful and historic Mississippi district, while eating brunch! This neighborhood is a perfect way to experience a food tour in Portland. The Mississippi district has been revived in recent years, while retaining its charm from yesteryear. Although there is a story tucked away in the past, and it will be told. These days however, it’s a Portland hotspot laden with music venues, quirky shops, cozy pubs, and eateries galore, ranging from casual to upscale and all things in between. You will not leave hungry! In this special brunch food tour, we will walk a total of .8 miles through the North Albina district and down Mississippi St, admiring vintage homes and historical brick buildings, all of which ooze charm., And of course, the hottest hipster hangouts, all while we visit six engaging foodie spots. All ages are welcome on this tour. The perfect tour for families!

Flowing out of ancient lava beds, the pristine McKenzie River meanders through some of the most lush and beautiful old growth forests in Oregon. As a class II and III river, it is appropriate for paddlers age 5 and older of any experience level. Your guides are well-trained and know the ins and outs of river rafting, so you’ve got nothing to worry about except having fun! Whether you’re looking for a mild or wild adventure we can accommodate you! Looking for a longer adventure? Check out our Full-Day trip which includes lunch!