Since 2018, OUT Central Oregon has hosted Winter PrideFest to celebrate Pride, Inclusivity, and a combined love for the outdoors. Now, over 1,500 participants flock to the gorgeous Cascade Mountains to party through a variety of events. Come celebrate the gayest event in the Cascades with us as we adventure from Portland, through the mountains to Bend, and Mount Bachelor!

I am so excited to host this LGBTQ+ group trip with our friends from First Nature Tours to celebrate Pride in our home state! We'll start the festivities in Portland with a full day taking in the sights of the Pacific North West. We’ll venture out in First Nature's luxury sprinter van to Mount Hood Meadows to enjoy lunch amongst Oregon's highest peak. Continuing onward to Bend, we'll embark on 3 days of winter pride festivities including the Campfire Hotel Pool Party, included group meals at a selection of our favorite restaurants in Bend, a guided snowshoe and bonfire experience on Mount Bachelor, the Winter PrideFest dance party, Drag Brunch, and more. There will also be plenty of time to hit the slopes on Mount Bachelor if you're looking to ski or snowboard!

Check out the itinerary below. We hope you can join for this epic weekend!!

Overview Welcome to Portland! Settle into our boutique hotel, Jupiter NEXT, in the heart of the city's east side. We'll spend the day getting a taste of Portland the way locals actually live it: coffee on Mississippi Ave, a wander through the endless rooms of Powell's City of Books, and time to explore a few of the city's most charming neighborhoods. In the evening we'll come together for an included welcome dinner, where the group can finally meet, connect, and officially kick off the weekend. Exact timing and meeting details will be shared in our group chat.

• Mississippi Ave & Powell's City of Books Stroll down Mississippi Ave, one of Portland's most vibrant and creative neighborhoods, then head to Powell's City of Books, where the rooms of books are almost as endless as Portland's love for coffee. Explore the world's largest bookstore, duck down Union Alley to shop, or grab a coffee at one of the many nearby cafés.

• Welcome Dinner — Included Meal Our first evening together includes a group dinner at a local Portland favorite, a relaxed introduction to the group and a great way to get to know your fellow travelers before we head for the mountains.

• Overnight at Jupiter NEXT, Portland We'll spend the night at Jupiter NEXT, a stylish, centrally located boutique hotel and a comfortable home base for our first night.

Overview After breakfast we'll load into First Nature's luxury Sprinter van and make the scenic drive toward Bend. On the way, we'll stop on the slopes of Oregon's highest peak, Mount Hood, for a short tour and an included lunch at the historic Timberline Lodge. Continuing over the Cascades, we'll break up the drive with a hike at Smith Rock, one of the most iconic natural monuments in the state, before rolling into Bend to check in at the Campfire Hotel, our home for the next three nights. Once we've settled in, we'll head out to Winter PrideFest's opening Snocial to get the weekend started, followed by a group dinner.

• Breakfast — Included Meal A great breakfast in Portland to fuel up before a day on the road and in the mountains.

• Tour & Lunch at Timberline Lodge — Included Meal Once featured in The Shining, Timberline Lodge is an Oregon architectural wonder set high on Mount Hood. After a short tour of the grounds, enjoy a decadent lunch buffet inside the lodge, including coffee and non-alcoholic beverages.

• Guided Hike at Smith Rock A perfect way to stretch our legs on the drive in. Smith Rock offers scenic views of deep river canyons and steep volcanic cliffs, and a walk around the base is truly awe-inspiring. It's one of the most beautiful spots in Oregon and sits right on our route into Bend.

• Check-in at the Campfire Hotel We'll arrive in Bend and check in at the Campfire Hotel, then take a moment to unwind and explore the property's amenities before the evening's festivities.

• Group Dinner at One of Bend's Favorite Restaurants — Included Meal Before the festival kicks off, we'll gather for an included group dinner at one of Bend's favorite restaurants. It's a great option for the evening, a chance to settle in, swap stories from the road, and fuel up together before we head over to the Winter PrideFest Snocial.

• Winter PrideFest 'Snocial' Join us for opening night! Mix and mingle with other queer folx and allies over food and drinks at Winter PrideFest's premier welcome event, featuring drag performances and more. This is the official kickoff to the festival weekend. Dress warmly!

• Overnight at the Campfire Hotel We'll settle in for the night at the Campfire Hotel, a retro-cool boutique hotel in the heart of Bend with a heated outdoor pool, hot tub, and cozy places to gather. It's the perfect home base, right in the middle of the festival action.

Overview Today the mountain is ours. Spend the day on Mount Bachelor however you like: add on skiing or snowboarding to hit the lifts, or keep it mellow with an afternoon back at the Campfire soaking in the heated pool and hot tub. Then, after dinner on your own, we'll head out for the most magical experience of the whole trip, a guided night snowshoe across Mount Bachelor that ends around a glowing campfire under the stars.

• (Optional Add-On) Ski or Snowboard at Mount Bachelor Add an all-mountain lift ticket for access to any open lifts for the day. A great option if you want to spend the day carving turns. (See Pricing for Friday and Saturday tickets.)

• Afternoon: Pool & Chill at the Campfire Warm up in the Campfire's heated pool and hot tub, or head into downtown Bend to explore the shops, breweries, and cafés at your own pace.

• Dinner on Your Own Dinner tonight is on your own so you can explore Bend's excellent restaurant scene. Your guide and hosts will share favorite recommendations, and there's always a group heading out together before we set off for the mountain.

• Guided Night Snowshoe & Campfire on Mount Bachelor — Included The highlight of the whole trip. We'll strap on snowshoes and head out across Mount Bachelor under the night sky, then gather around a glowing campfire for spiked hot cocoa, stargazing, and fantastic stories. It's the kind of night in the outdoors you've never experienced before, quiet, magical, and unforgettable. All equipment provided, just dress warm.

• Overnight at the Campfire Hotel Back to the Campfire for a cozy night in the heart of Bend. Warm up in the heated pool and hot tub, gather with the group, or rest up for the festival's biggest day tomorrow.

Overview Our biggest day of the festival. We'll kick things off with the drag brunch in the morning, then head up to Mount Bachelor for the afternoon Pride Lodge Party, with optional skiing, snowboarding, or a lesson for anyone who wants time on the slopes. Back at the Campfire, we'll celebrate at the annual pool party, gather for our group farewell dinner, and close the weekend with the grand finale, the Winter PrideFest Dance Party. (Winter PrideFest sets its final schedule closer to the event, and timing shifts year to year, so the exact order of the day may change.)

• Drag Brunch (Morning Drag Show) We start the day with the festival's drag brunch, a lively morning drag show to kick off our final day of Winter PrideFest. It's a "brunch" in name and timing, so the show runs during brunch hours, with food and drinks available to purchase on your own. A fun, only-at-Pride way to start the day.

• (Optional Add-On) Skiing, Snowboarding or Lessons at Mount Bachelor For anyone who wants time on the mountain, add an all-mountain lift ticket for skiing or snowboarding, or book a lesson if you're new to it. Transport to and from Mount Bachelor is provided. One heads-up: the morning drag brunch show and mountain time overlap, so if you're set on a full day of skiing you may trade off the drag brunch show. We'll help you plan once the festival's final schedule is released. (See Pricing for lift tickets.)

• Pride Lodge Party at Mount Bachelor Winter PrideFest's afternoon lodge party brings the celebration up the mountain, with a DJ, drag, and dancing in the scenic setting of Mount Bachelor's West Village Lodge. A festival favorite.

• Winter PrideFest Pool Party Back at the Campfire, grab your swimwear and head to the outdoor heated pool for the annual pool party, one of the festival's signature events, celebrating Pride with the whole community.

• Farewell Dinner — Included Meal Put on your dance-party best and join us for one last fantastic dinner all together at a Bend favorite before the big night out.

• Winter PrideFest Dance Party The main event. Our queer dance party features a special emcee and drag performances, a space for all queer people and allies to come together and dance the night away. Included with your trip.

• Overnight at the Campfire Hotel Our final night at the Campfire Hotel in Bend. Kick off your dancing shoes, soak in the hot tub, and get some rest before our farewell brunch in the morning.

Overview One more gathering before we go. We'll come together in Bend for an included farewell champagne brunch and a toast to the weekend, then set out toward Portland the scenic way, through the Columbia River Gorge with a stop at the iconic Multnomah Falls. We're planning an earlier, easier travel day so you can catch afternoon or evening flights without a rush.

• Farewell Champagne Brunch — Included Meal We close out the trip with a relaxed group brunch and a champagne toast, a chance to share stories and soak in the last few hours together before we hit the road. Brunch includes a main dish, champagne, coffee, and water.

• Stop at Multnomah Falls On our way back to Portland, we'll pull off in the Columbia River Gorge for a stop at Multnomah Falls, Oregon's tallest waterfall at 620 feet and one of the most photographed spots in the state. A gorgeous final postcard before we say our goodbyes.

• Return to Portland & Departures After brunch and our Gorge stop, we'll make our way back to Portland, arriving by late afternoon. Departures: If flying out of PDX (Portland), we recommend booking a departure after 6:00 PM PST to allow for brunch, the drive, and our Multnomah Falls stop. If flying out of RDM (Redmond), you can join brunch and then catch an afternoon flight from nearby Redmond instead of driving back to Portland, since the festival wraps the day before and our Smith Rock hike happens on the way in. Prefer not to rush? Add a post-trip night in Portland or an extra night in Bend (see Pricing).