Top 6 Things to Do in Bend, Oregon for Winter PrideFest
Photo by Dylan M Howell
Every March, Bend fills up with LGBTQ+ travelers for Winter PrideFest, a weekend of skiing, hiking, and amazing parties set against the Cascades and the High Desert. If you're planning a trip around it, here's where to spend your time.
As one of the top travel destinations in Oregon, it can be easy to get overwhelmed with the number of options of things to do in and around Bend. One of the best aspects of Bend is it’s geographic location and the diversity in landscape this lends and SideQuests is coming home in 2027 for Winter PrideFest to show our guests exactly how to do gay travel right! As the Cascade Mountains meet the High Desert in Central Oregon, a diverse and dramatic landscape beckons to be explored. From hiking, rock-climbing, skiing and snowboarding, camping and whitewater rafting, there are tons of tour options to explore for the adventurous soul.
Here are the top things to do in Bend based on our experience as locals and hosts!
If you’re looking for somewhere to stay, check out The Campfire Hotel. This classic mid-century modern accommodation comes complete with an enormous heated pool and campfire pit, ready to welcome you.
Michael and I are so excited to be hosting a gay travel trip in March for an event that is near and dear to our hearts. We have hosted gay travel groups all over the world, but there is something special about hosting a trip in our backyard and showing our followers and guest the place we call home.
As residents of this beautiful state, we are familiar with Winter PrideFest and the unique way it brings people together. From humble beginnings, we are astounded at how many people now flock to Bend and with us at the helm you can be sure to experience everything special about this event through our eyes.
We are going to leave no stone unturned to show you amazing hikes, beautiful landscapes, great spots to eat and drink, and share the hospitality of one of the greatest places on earth, so make sure you don’t miss this in March 2027!
2. Hiking and Rock Climbing at Smith Rock State Park
Smith Rock is one of Oregon’s Natural Wonders. Millions of years ago, a combination of volcanic, seismic, glacier movement carved this dramatic landscape in the high desert. Located 35 minutes outside of Bend, this iconic destination is renowned for its towering rock formations, deep river canyons, and panoramic vistas. Trails wind through rugged terrain, offering hikers of all levels the chance to explore the park's diverse landscape and groves of juniper.
From leisurely strolls along the Crooked River to challenging ascents up Misery Ridge, there are plenty of hiking trails to choose from. Smith Rock is also one of the top rock climbing destinations in the Pacific Northwest. Smith Rock is known as the birthplace of sport climbing in the U.S. perfectly formed solid walls of rock make for an ideal scenario for belay climbing or bouldering. As part of a SideQuest gay trip, we make this journey a must-see
For hiking: it can be as easy as walking down a dirt path for about a quarter mile, to as difficult as traversing up rugged and rocky trails. There’s something for everybody. There’s even a paved pathway from the parking lot to the first and primary viewpoint, making Smith Rock State Park fully enjoyable and accessible.
3. Travel with First Nature Tours
First Nature Tours is an LGBTQ+ owned and operated outdoor adventure company with a variety of tours from white-water rafting, thrilling hikes, and camping adventures. SideQuests, regular use them as a provider during and you should totally check out a few of their top tour offerings in Central Oregon and Bend below:
Image courtesy of First Nature Tours
A 6-day outdoor adventure that includes exhilarating activities such as whitewater rafting and an optional bungee jumping experience, in addition to relaxing and rejuvenating activities like yoga in the park and a sunset picnic. This tour is perfect for outdoor adventure enthusiasts!
Central Oregon Outdoor Family Adventure
This elevated, family-friendly adventure combines luxury experiences with the great outdoors. Embark on a safari-style camping trip along the Deschutes River, followed by a stay at the extravagant Brasada Ranch. Enjoy exciting activities such as horseback riding, lava tube exploration, whitewater rafting, and more!
Central Oregon Regenerative Corporate Retreat
Embark on a transformative corporate experience with an emphasis on regenerative travel. Teams will engage in a reforestation stewardship project along the Deschutes River, participate in team-building exercises at Smith Rock State Park, and embark on an underground cave and distillery tour.
Fly-Fishing Weekend in Central Oregon
Perfect for those that love being on the water, this weekend getaway includes a variety of activities from fly-fishing, rafting, and camping along the river. Go beyond the water with exciting activities such as mountain biking or rock climbing, making the most of the great outdoors.
Image courtesy of Wanderlust Tours
4. Guided Snowshoe & Bonfire with Wanderlust Tours
This is something you won’t want to miss. As someone new to snowshoeing, trekking through the mountains beneath the starry sky seemed truly enchanting, but I was nervous about how difficult it could be. Once you start, you’ll realize that it’s a pretty easygoing activity. The journey guides you to a beautifully crafted snow amphitheater, where snow-carved chairs circle a warmly glowing bonfire. Treats and drinks are waiting such as hot cocoa, forest desserts, and even better: Hazelnut Espresso Vodka to enhance your warming beverage. Savor the serenity of the Deschutes National Forest by night, and enjoy this leisurely hike amongst the stars.
5. Experience the Outdoors at Fir Haven Retreats
Fir Haven Retreats is an LGBTQ+ owned and run project established in the heart of the Columbia River Gorge. Spanning 20 acres, the property will contain 14 contemporary A-frame cabins nestled amidst lush pine forests, as well as designated areas for traditional tent camping. With a focus on fostering regenerative tourism, guests can partake in stewardship activities such as salmon restoration and trail maintenance. A shared base-camp facility will offer wellness amenities including an Onsen-style cedar hot tub, a sauna with a cold plunge, a yoga platform for stargazing, and a communal campfire area. Fir Haven Retreats prides itself as a Pacific Northwest hub for eco-conscious travelers.
6. Ski and Snowboard at Mt. Bachelor
As one of the top skiing and snowboarding destinations in the Pacific NorthWest, Mt. Bachelor Ski Resort offers an unparalleled adventure amidst breathtaking alpine scenery. Located just 21 miles from Bend, approximately 25 minutes drive, this iconic resort boasts over 4,300 acres of skiable terrain, catering to all skill levels from beginners to seasoned experts. With its consistent snowfall and diverse terrain composed of groomed slopes, bowls, and gorgeous tree runs, Mt. Bachelor provides endless opportunities for exhilarating runs and unforgettable moments on the slopes.
If you’re a beginner we partner with a great company that offers ski and snowboard lessons daily along with a variety of bunny-hills to practice. Whether carving through pristine powder, navigating through glades, or enjoying panoramic views from the summit, Mt. Bachelor has something memorable to offer anyone who visits.
There are virtually endless options when it comes to outdoor activities in Bend Oregon. The region of Central Oregon is where the Cascade Mountains meet the High Desert. With access to volcanos, caves that cut deep into the earth, state and national forests, mountains and ski resorts, dramatically carved rock structures, and rivers perfect for white water rafting. Whichever activities fit your travel schedule and your budget, it’s sure to be a great addition to your itinerary.
Bend’s LGBTQ+ community is up and coming. Many gay-friendly and gay-owned businesses are starting to open in Bend’s downtown and Old Mill Districts. With Winter PrideFest being a major highlight of the winter season, LGBTQ+ business owners are setting up shop and expanding the network of gay-friendly travel destinations in Oregon.
For gay-friendly places to stay in Bend, check out the Campfire Hotel, and many more below:
SideQuests is proud to support Bend, Winter PrideFest with our very own gay group trip. Oregon is our home and we are really looking forward to sharing it with our guests. We are so excited to have you join us so make sure you sign up soon.
Frequently Asked Questions
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Join a SideQuests-hosted LGBTQ+ trip, hike or climb at Smith Rock State Park, tour with LGBTQ+-owned First Nature Tours, take a guided snowshoe and bonfire with Wanderlust Tours, stay at Fir Haven Retreats, go to Winter PrideFest itself, and ski or snowboard at Mt. Bachelor. Book with SideQuests and we'll take you through all of it as a group.
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Yes. Bend's LGBTQ+ community is growing, with gay-friendly and gay-owned businesses opening around downtown and the Old Mill District, and Winter PrideFest now draws over 1,500 people every March. Traveling with a SideQuests group makes it easier, you get the outdoor adventure Bend is known for alongside a community that is inclusive and loves to have a good time!
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Winter PrideFest is an annual LGBTQ+ celebration in Bend, organized by OUT Central Oregon every March. It started in 2018 with about 150 attendees and has grown to over 1,500, built around a shared love of Pride, inclusivity, and the outdoors.
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No. Many guests come on their own and leave with new friends. We host the group personally, so it's a small, welcoming crowd built around Winter PrideFest, not a random tour group.
As one of the top travel destinations in Oregon, it can be easy to get overwhelmed with the number of options of things to do in and around Bend, especially during Winter PrideFest.
Here are the top things to do in Bend from a local who is proud to call Oregon home