Travel is all about freedom, be it to try new things or to return to those you love. Who you hit the road with plays a big part of that, of course, and tour companies all around Oregon stand ready to welcome travelers of all stripes. Whether you’re looking to hone your outdoor skills or experience places from a new point of view, these trips pack in the fun while fostering a sense of community. Here are some trip ideas that bring like-minded people together.

Women-Only Trips That Up Your Game
For years Serena Bishop Gordon worked for corporations before she found her calling in the outdoors — specifically, on a bike zipping along dirt roads and trails. These days Bishop Gordon, who lives in Bend, races and trains around Central Oregon and beyond, and has channeled that love for bikes into Special Blend Gravel, a company that puts on camps and events for women looking to up their game on two wheels in any season. Sign up for her three-day spring edition in April and you’ll spin down the gorgeous gravel roads of the Columbia Plateau near Dufur under the tutelage of professional coaches. Camps are for intermediate and advanced riders looking to build confidence, to refine skills and to push each other to be their best. “We aren’t asking for a seat at the table,” she explains. “We are building our own.”
If floating down a magnificent river, mountain biking world-class single-track and doing some yoga while honing your outdoor skills seems appealing, check out the women-only retreats offered by Bend-based AdventurUs Women. The women- and LGBTQ+-owned outfitter organizes numerous trips for women of all ages and abilities. In May there’s a four-day retreat in Bend made for newcomers to the outdoors, as well as those with some experience. Each day will bring a new activity, like kayaking or paddleboarding, rock climbing and snowshoeing, depending on conditions. Want to spend more time on the water? Orange Torpedo Trips offers four-day women-only kayaking trips down the Rogue River, as well as trips that combine hiking or trail running from inn to inn along the 40-mile-long Rogue River Trail.

Accessible Adventures by Land, Air and Tree
Oregonians pride themselves on sharing the natural wonders of the state with everyone and anyone, including those with mobility challenges. Groups like Adventures Without Limits, a nonprofit, organize camping trips, surf camps and more for people of all abilities, including those in wheelchairs. In Cannon Beach, Bahama Boards offers adaptive surf lessons seven days a week — be sure to call ahead to discuss your needs.
Bend-based Wanderlust Tours has become well known for its canoeing, caving and snowshoe tours that often involve craft-beer tastings. Now Wanderlust has partnered with AdvenChair, a company that makes rugged all-terrain wheelchairs to get visitors into the region’s most stunning locations. These guided trips, called AdvenTours, include excursions for wheelchair users and their friends and families to Smith Rock State Park, hiking and stargazing around the Newberry National Volcanic Monument and trips to Benham Falls along the Deschutes River.
For an epic adventure, head to Silver Falls State Park near Salem, Oregon’s largest state park, and sign up for an outing with Tree Climbing at Silver Falls. The company comes exactly as billed, with adventures designed to take you up high into the park’s tremendous stands of old-growth trees. Using harnesses, ropes and powerful motorized ascenders, guides can hoist people who use wheelchairs more than 200 feet up into a Douglas fir tree for bird’s-eye views of the Cascades and the Willamette Valley, making it a communal adventure everyone can enjoy. If you’re coming from Portland, ask about hitching a free ride with the guides who’ll be commuting from there to the park, too.
In Eastern Oregon, Joseph-based Bigfoot Helicopters offers scenic flights of the Wallowa Mountains. Book a flight and you’ll soar over the Imnaha River, one of Oregon’s lesser-known but truly outstanding canyons — a tributary canyon to the more famous Hells Canyon. The company’s owned by Andrew Kilgore, an Air Force veteran. You’ll need to be able to get in and out of the helicopter yourself and must weigh under 260 pounds, but otherwise Kilgore can work with anyone — especially other vets — to showcase the region by air.

Guided Trips Specializing in Diversity and Inclusivity
The nonprofit Wild Diversity is on a mission to get more LGBTQ+, Black, Indigenous and people of color into the outdoors by fostering community and making adventures fun and safe for all. To do that, the company hosts adventures, workshops and more. Organized trips can include mountain biking, whitewater rafting, horseback riding and just going for a swim together. Check the website and Facebook pages for upcoming events.
Rainboats, an outfitter that calls itself “powered by pride but straight-friendly,” is the brainchild of Kathy Redwine, who loves to share the Coast by kayak with like-minded and kind-hearted visitors. Sign up for a two-hour personalized tour and you’ll head out into quiet bays and rivers along the Central Coast near Newport in small groups of no more than four people. No experience necessary, and tours happen all year as long as conditions are safe.