Get ready to explore the wild beauty of Oregon—these adventures will leave you breathless!
From misty coastal cliffs to snow-capped mountains, 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. Lace up your hiking boots, grab your sense of wonder, and dive into Oregon’s most iconic, awe-inspiring outdoor experiences. Your adventure starts now.
1. 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.
Willamette Valley B&Bs
2. Ice skate in downtown Portland: The all-new Portland Winter Ice Rink features pop-up shops, eateries and an outdoor ice rink under the Morrison Bridge in downtown Portland.
3. Hit the slopes: Fresh powder and bluebird skies await at Oregon ski areas. Take ski or snowboarding lessons at Mt Hood Meadows Ski Resort. Known for night skiing, Mt. Hood Skibowl also offers night snowtubing with music and colorful lights.
Mt Hood Bed and Breakfasts
4. Go bird-watching in the Willamette Valley: Watch dozens of species of migrating and resident birds
5. Visit Kam Wah Chung State Heritage Site: Learn about John Day area history through the prism of its earliest Chinese residents at the Kam Wah Chung State Heritage Site. Journey Through Time on the John Day Scenic Byway.
Wilson Ranches Retreat in Central Oregon
6. Tour the Hood River Fruit Loop: Between late March and mid-May, thousands of cherry, apple and pear trees cover the Hood River Fruit Loop in a blanket of white and pink blossoms. Sip estate-grown cider, pick up goodies at a farm store and soak up the beauty of Hood River Valley any time of year
7. Stargaze at Oregon’s first dark-sky park: Pitch a tent under starry night skies at Prineville Reservoir State Park — Oregon’s first International Dark Sky Park — where rangers lead educational programs in summer. Learn more about Oregon’s Magnificent Dark Skies.
8. Enjoy a car-free trip to the Columbia River Gorge: Kick back with a car-free trip to the Columbia River Gorge, where shuttles stop at the base of world-famous waterfalls and in charming communities. Several popular waterfalls are wheelchair-accessible.
9. 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.
10. 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.
11. Spy migrating gray whales: Between mid-December and mid-January, nearly 20,000 gray whales migrate south past the Oregon Coast. See the animals from the Whale Watching Center in Depoe Bay, and learn more from helpful volunteers during Whale Watch Week.
12. Chase a waterfall, or two, or more
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.
Gift certificates are no longer available for purchase through our organization. We encourage you to contact our member inns directly to purchase gift certificates.
If You Currently Hold an OAII or OBBG Gift Certificate:
- Your gift certificate does not expire
- Certificates may be redeemed at participating Oregon Association of Independent Inns properties.
Thank you for supporting Oregon’s Independent Inns and lodging properties over the years. We’re grateful to everyone who has shared the gift of lodging through the OAII Lodging Gift Voucher Program.
As of June 1, 2026, the Oregon Association of Independent (formerly the Oregon Bed and Breakfast Guild – OBBG) discontinued the program, and gift certificates are no longer available for sale. However, existing gift certificates remain valid and may still be redeemed.
The Oregon Association offers a wide variety of inns, from a small guest cottage or two-room bed and breakfast to a larger country inn or dude ranch. If you need assistance locating a participating property or have difficulty redeeming your certificate, please contact us—we’re happy to help.
Important Notes:
- All OAII properties accept association gift certificates. Click here to view participating properties.
- Gift certificates are treated as cash and cannot be replaced if lost, stolen, or destroyed.
- Certificates may only be redeemed at active OAII properties
- Individual property policies apply, including restrictions on availability, packages, or special offers.
Questions or Assistance:
If you have questions about redeeming a gift certificate or need help planning your stay, please contact E-mail info@obbg.org or call OAII at 503-893-4210. Please leave a message as this line is monitored by our busy innkeepers.
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.
