From misty coastal cliffs to snow capped mountains, to ancient forests to high desert plains, Oregon is a land of stunning contrasts and unforgettable experiences. Whether you’re a thrill-seeker or a nature lover in search of serenity, this list of must-do adventures has something for everyone. Grab your sense of wonder and dive into Oregon’s most iconic, awe-inspiring outdoor experiences. Your adventure starts now.
National Plan for Vacation Day – January 27, 2026
On January 27 take time to plan your days off for the year. And if you need some inspiration let the Oregon Association of Independent Inns assist and inspire your 2026 travel plans with these Top 26 Oregon Adventures for 2026. Make 2026 the year you stick to your goals and turn boring New Year’s resolutions into travel opportunities. Let’s make 2026 epic.
Oregon Inns have joined the 2026 Vacation Day party and are offering a 20% discount for a two or more night stay during 2026. Maybe plan a few 2026 get aways. We hope to inspire you to Explore Oregon. Applies to new reservations only
1 – Discover the Historic Oregon Trail. Hit the trail, inspire your own pioneer spirit, stand in the actual wagon ruts pioneers left behind, and visit the numerous interpretive sites, monuments and cultural centers along the way.
2 – Whale Watching on the Oregon Coast – Gray whales cruise along the Oregon coast en route from Alaska to Mexico, spouting geyser-like blasts of spray as they go. Whales are visible from Oregon’s shores year round. Even more during the winter and spring migrations. Oregon State Parks celebrates the migration twice per year during Whale Watch Weeks in late December and late March. Thanks to towering coastal bluffs and a string of beaches set aside as state parks, Oregon offers visitors front-row seats for whale watching.
3 – Finders Keepers in Lincoln City Oregon – More than 3,000 artisan-made floats will be placed along Lincoln City’s seven miles of shoreline. Inspired by the historic Japanese fishing floats that once washed ashore, this one-of-a-kind program invites
visitors to slow down, wander, and experience the coastline with a sense of wonder.
4 – Skiing and Winter Sports – Oregon offers unparalleled opportunities for skiing and winter recreation. Whether you are a skier, snowboarder, or looking for backcountry trails for snowshoeing, cross-country skiing and snowmobiling, Oregon has it all. Some inns offer special ski packages and all are glad to share their favorite spots with you. After your day’s adventure, curl up at a cozy and warm bed and breakfast of the Oregon Bed and Breakfast Guild.
5 – Discover the Breathtaking Beauty That Defines Oregon – Oregon boasts the deepest lake and the deepest canyon in the nation, yet Crater Lake and Hells Canyon are only the start of a wild paradise. Explore unique experiences, charming towns, and stunning natural wonders that define this captivating state. This is a land that dares you to pack your bags and discover what’s waiting around the next bend.
6 – Celebrate cellar season: Ring in the new year with cellar season — a time when Willamette Valley winemakers throw a log in the fireplace, offer behind-the-scenes tours, and host cozy events at less-crowded wineries and tasting rooms between January and March.
7 – Set out on an Oregon wine getaway into Oregon’s best wine regions. The hospitality you’ll find at am Oregon Independent Inn is like no other. Add to that Oregon’s cooler climate and signature grape – Pinot Noir – and you’re in for an unforgettable experience.
Travel Oregon with Yeti and Squatch
8 – Superb Oregon Birding Locations Oregon’s diverse and spectacular landscape provide varied habitats ranging from sandy beaches to alpine meadows. More than 500 species of birds call Oregon home year round or migrate through, sometimes stopping to nest.
9 – Oregon’s Indigenous heritage is a rich history of deep connection to the land, with evidence of human presence for over 12,000 years. The heritage includes a diversity of languages, complex trade networks, spiritual practices, and a legacy of resilience against historical challenges like termination policies and assimilation attempts.
10 – Feast on Oregon Food Trails: Stop along any of the Oregon Food Trails on your next road trip for seasonal produce, creative craft beverages and farm-to-table dining.
11 – Gaze into Oregon’s Magnificent Dark Skies, some of the largest expanses of magnificent dark skies in the US. There are few experiences as humbling as staring into the cosmos
12 – Chase a waterfall, or two, or more – According to Northwest Waterfall Survey there are well over 1000 waterfalls in Oregon! We’ve set out to witness the beauty of as many as we can. We’ll share our finds with you, our guests, so you too can set out to Chase Waterfalls.
13 – Geocaching – Many innkeepers of the Oregon Independent Inns are avid cachers and you’re sure to find many caches near their inn when doing a search.
14 – Take an Oregon Bike-cation – Oregon scenic bikeways are the place for avid cyclists! Did you know Oregon has the ONLY Scenic Bikeway program in the United States? We have 17 scenic bikeways in Oregon! Get ready to ride across desert highways, pedal past geological wonders, and marvel at the sea.
15 – Embark on a Sustainable Travel vacation – Sustainable travel remains a priority for travelers who want more fulfilling and meaningful experiences. Taking the road less traveled is back on the table as well as unique shoulder month experience.
16 – Explore Oregon historic Lighthouses – Oregon Lighthouses were built to warn ships of the dangerous rocky shores. The treacherous Pacific storms wrecked many a ship but the lighthouses prevented even more from such fate.
17 – Hop on an Oregon Wine Tour – Oregon is full of passionate people who love to guide tours and enlighten visitors about our amazing state. Let’s make a plan to explore Oregon this year. Tour operators can enhance your visit to Oregon with safe and memorable experiences, providing insider secrets, and with all the food and drink Oregon has to offer.
18 – Take a food tour: Get the inside scoop on Portland’s culinary scene with an expert guide like Lost Plate Food Tours, which explores downtown eateries, food-cart pods and more.
19 – Historic Covered Bridges – Oregon has the largest collection of historic covered bridges in the western part of the United States, with over 50 covered spans.
20 – Ride the Wallowa Lake Tramway. the steepest four-person gondola ride in North America. The exciting trip to the top of the mountain allows one to enjoy the 4000′ view as the gondola rises above the blue waters of Wallowa Lake. Once on the top enjoy over 2 miles of trails in the alpine wilderness and spend a day seeing into four states.
21 – Oregon’s Scenic Byways aren’t about getting somewhere fast. They’re about seeing Oregon as it’s meant to be experienced—curious, unhurried, and just a little bit awe-struck the whole way.
22 – Let your inner Cowboy or Cowgirl out at a 9,000 acre working cattle ranch in Central Oregon for an authentic Ranch experience.
23 – Follow the Grapes and take a vineyard walk on a Vineyard Practices 101 tour
24 – Winery Itinerary Tour Service. Let a Willamette Valley Winery innkeeper arrange your day of wine tasting.
25 – Experience of the “Edible B” at an Oregon Independent Inn. There is no better way to experience the best of Oregon Bounty than at the breakfast table of our inns throughout the state.
26 – Ride the Crater Lake Rim – hop on one of the three historic-looking trio passenger trolleys from The Crater Lake Trolly.
We Love Oregon! We know you will too. So Ask an Innkeeper. Oregon is one of a kind: a place where you can hike to breathtaking vistas, then dine on fresh, local and organic farm-to-table products; a place for award winning wines, scenic byways and magical waterfalls; a place we’re lucky to call home.
Since 1989, the Oregon Bed and Breakfast Guild has served as a statewide information network for its member properties, providing a unified voice for the industry with state regulatory and tourism agencies.
Now known as The Oregon Association of Independent Inns, we’re the same trusted organization, with a new name, a fresh look, and an expanded focus on independent lodging properties beyond traditional bed and breakfasts. Member properties represent a wide range of accommodations, from small guest cottages, cabins, and intimate two-room B&Bs to larger country inns, boutique hotels and dude ranches.
Oregon Association of Independent Inns are ready to share Oregon with you: it’s environment, culture, and heritage. Combine gracious hospitality with ambiance at an inspected and approved member of the Oregon Association of Independent Inns.
