Bend Winter PrideFest Gay Group Trip: Portland, Mount Bachelor & Bend, Oregon
5 Days, 4 Nights
February 24th-28th, 2027
About This Trip
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!!
Capped at 13 Travelers!
Limited Earlybird Spots Left! Save $100
Deposit: $488 (just 25% down)
$2,050
$1,950
2027: Feb 24 - Feb 28
Portland - Bend - Mount Bachelor
Early Bird Discount - Save $100!
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This is the reason we're all here. Since 2018, OUT Central Oregon has thrown Winter PrideFest, the gayest weekend in the Cascades, and what started small now draws more than 1,500 people to Bend for a few days of drag, dancing, snow, and community. Across the weekend you've got the opening Snocial, parties on the mountain, the Campfire pool party, drag brunch, and the big Winter PrideFest Dance Party to close it all out. Doing it as a group means you walk in with your people already around you, no standing awkwardly at the edge of the room. We handle the logistics so you can just show up and celebrate.
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This year we're building in real time to enjoy our home city before we head for the mountains. Your first night opens with a welcome dinner at one of Portland's most-loved restaurants, a relaxed way to meet the group over some of the best food in the city. From there, the pace is yours. Lose an afternoon inside Powell's City of Books, the largest bookstore in the world, wander the galleries, boutiques, and cafés of the Pearl District, grab coffee on Mississippi Ave, and hit whichever of Portland's top sights call to you. Michael and Matt live here, so you'll get the local list of where to eat, drink, and explore.
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Strap in and get out into the snow on a guided snowshoe experience through the forest near Mount Bachelor. Fresh air, insane views (more stars than I’ve seen anywhere else), and a campfire with drinks - snacks and great community. (this was my favorite part of the trip last time)!
Tour Highlights
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With a small group of LGBTQ+ folks (capped at 13), a First Nature local guide, and host Matt the whole way. It’s the kind of trip where you leave with a community that surprises you and sticks around.
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Every year the Campfire Hotel's heated outdoor pool turns into one of Winter PrideFest's signature scenes. Picture a steaming pool and hot tub ringed by snow, music going, and a crowd of queer folks and allies celebrating Pride together. Because our whole group stays right on property, it's a few steps from your room to the party and back to warm up. Bring your swimwear and settle in, this is one of the most fun afternoons of the whole weekend.
What’s Included?
Pricing:
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Traveling solo and want the extra space? Not everyone wants to share. Add the private room option to have your own quarters at both hotels for the trip.
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Flying in early or just want to settle in before we begin? Reserve a night at our host hotel, Jupiter NEXT, before the trip starts. Your booking will be linked so you don't have to check out and check back in on Day 1.
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Want to hit the slopes? Add an all-mountain lift ticket for Friday, March 5, good for skiing or riding on any open lifts that day. Rentals available separately at the mountain.
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Add an all-mountain lift ticket for Saturday, March 6, our group day on the mountain, good on any open lifts. Ski or snowboard alongside the group, then meet up for snowshoeing and pool time. Rentals available separately at the mountain.
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Not ready to rush to the airport? Add a night at Jupiter NEXT after we return to Portland on the final day, linked to your stay so there's no room change. Great if you'd rather fly home relaxed the next morning.
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Flying out of Redmond (RDM) or want a little more festival time? Add a night at the Campfire Hotel in Bend and catch your flight from nearby Redmond instead of returning to Portland with the group.
Not sure which add-ons you want to book? No worries! Add-ons can be added or subtracted from your reservation until 90-days before the start of the trip!
Add-Ons:
Only a 25% deposit is due to book. The remaining balance isn't due until 90 days pre-trip. Your deposit is 100% refundable until the trip is confirmed (that's when 12 travelers have booked). Prefer monthly payments? Some guests use Affirm's virtual card at checkout.
See the full cancellation policy ↓
Navigation:
Tour Highlights — What’s Included — Pricing— Itinerary — Your Host — FAQ — About — Hotels
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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.
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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.
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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.
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We'll spend the night at Jupiter NEXT, a stylish, centrally located boutique hotel and a comfortable home base for our first night.
Day 1
Welcome to Portland!
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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.
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A great breakfast at one of Portland’s prized locations before a day through the mountains.
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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 all-you-can-eat lunch buffet inside the lodge, including coffee and non-alcoholic beverages (alcoholic beverages available for purchase).
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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.
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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.
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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.
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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!
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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.
Day 2
Over the Mountains: Timberline Lodge, Smith Rock & Bend
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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.
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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.
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Back at the hotel, warm up in the heated pool and hot tub, or head into downtown Bend to explore the shops, breweries, and cafés.
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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.
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Back to the Campfire for another 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.
Day 3
Mount Bachelor: Ski, Relax & a Night Snowshoe Under the Stars
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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.)
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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 drinks available to purchase on your own. A fun, only-at-Pride way to start the day.
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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.
Plus: 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.
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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.)
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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.
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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.
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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.
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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.
Day 4
Festival Finale: Drag, Pool Party, Farewell Dinner & the Dance Party
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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.
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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.
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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.
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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. Prefer not to rush? Add a post-trip night in Portland (see Pricing).
Day 5
Brunch, Multnomah Falls, Return to Portland & Departures
Meet Your Host
Matthew is the founder of SideQuests Travel and one half of the LGBTQ+ travel brand Michael & Matt. He started SideQuests because he was tired of trips that felt like checklists instead of connection, and wanted to build a space where you can show up exactly as you are and instantly feel like you belong. What began as a group-trip experiment turned into a full mission to fight loneliness and build queer community on the road.
This trip is personal. Matthew lives in Portland, and Oregon is home, so Bend Winter PrideFest isn't a destination he researched, it's his backyard. He knows which Portland coffee shop to send you to, where to look on the drive over Mount Hood, and how to turn a van full of strangers into a group of friends by the first dinner. Warm, organized, and always up for a good time, he'll take care of you from the welcome dinner in Portland to the final champagne toast in Bend.
His whole philosophy is that the best journeys aren't about where you go, they're about who you find along the way. Come see his home state with him, and leave with a new group chat that outlasts the snow.
Frequently Asked Questions
Have questions specific to this trip? Here are some common questions about our adventure.
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Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s-60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.
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We keep our groups intentionally small—typically 16-24 travelers—to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.
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Each trip is slightly different, but most SideQuests include:
Boutique accommodations
Most meals (with options)
Excursions + guided activities
A bilingual local guide
Private group transportation
Your hosts (hi, that’s us!)
You can view all the trip-specific inclusions on each individual trip page. Airfare to and from the destination is not included. You'll receive a detailed packing list and itinerary before departure.
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If your booking is still pending (meaning the trip hasn’t been confirmed yet), you’re eligible for a full refund — including your 25% deposit.
Once the trip is confirmed (after 12 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher for the amount paid (minus a $100 cancellation fee).
After the 90-day mark before the trip, all payments become non-refundable, since hotels, transportation, and activities have already been paid for. Any exceptions at that point are at the discretion of our local partners.
We strongly recommend purchasing travel insurance — it really is worth it.
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You can reserve your spot with a 25% deposit and pay the rest in installments through Affirm. In order to do this, you must register a virtual card through Affirm.
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Yes! Most people do. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends (and at least one new group chat). SideQuests are specifically designed to foster connection, so coming alone is actually the perfect way to experience our trips. We create plenty of opportunities to bond with the group while also respecting everyone's need for personal space and independence.
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Not at all! Our trips are great for all experience levels. We’ve got you. Our trips are built with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don’t need to be a seasoned traveler, just someone ready to say yes.
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We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, single supplements are available for an additional fee (listed during checkout).
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Not at all! While our trips are centered around queer community and joy, allies are absolutely welcome — as long as you’re here with respect, openness, and a good sense of humor!
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Most trips include a mix of walking, light hikes, or outdoor activities — but we always include downtime, optional excursions, and flexible pacing. You do you, with a group that gets it.
For this tour specifically, the hike at Smith Rock is mild, with about 1 mile in length with inclines and declines. Snowshoeing can require stamina. The pace is leisurely but requires the ability to walk long distances. And, skiing and snowboarding is to each traveler’s discretion and passes are available as add-ons to the main tour. -
We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.
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Fly into Portland (PDX) where the trip begins; head home from PDX or, if easier, Redmond (RDM) near Bend. Please. note that if you fly out of RDM, you will miss the stop to see Multnomah Falls with the rest of the group en-route back to Portland.
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March 3rd to March 7th. Dates confirm once the festival schedule drops. 5 days/4 nights, starts with the Portland welcome dinner (arrive PDX by early afternoon that day), ends back in Portland by late afternoon on the final day, so PDX departures after 5 PM.
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Bend is a welcoming mountain town in Central Oregon, and Winter PrideFest has been a celebrated LGBTQ+ event since 2018, hosted by OUT Central Oregon. Expect cold, snowy weather in early March, so pack accordingly. For more general questions about SideQuests trips, visit sidequeststravel.com/faq.
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Absolutely. Bend is a welcoming mountain town in Central Oregon, and Winter PrideFest has been a beloved local celebration since 2018, hosted by OUT Central Oregon. Each year more than 1,500 people come out for a weekend of queer joy in the Cascades, so you'll be surrounded by community the whole time.
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Winter mountain conditions. Bend in late February and early March usually sees daytime highs in the upper 40s to low 50s°F and lows around freezing, with snow on Mount Bachelor and often in town too. Portland is milder and wetter, typically 45 to 55°F and rainy. Come ready for cold, snow, and a bit of everything.
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Think warm and layered. A warm water-resistant snow jacket. Snow pants if you plan to ski or snowboard, insulating layers, a hat and gloves, and warm, water resistant shoes. For our snowshoeing excursion, gear, snow-pants, and snow-shoes will be provided. Bring swimwear for the Campfire pool party and hot tub, an outfit you can dance in for the Dance Party, and sunglasses and sunscreen for bright days on the mountain. We'll send a full packing list before departure.
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For festival details, check OUT Central Oregon. For general questions about SideQuests trips, visit sidequeststravel.com/faq. Once you book, you'll join our group chat where we share everything you need before the trip.
About SideQuests Travel
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Hi, I'm Matthew, co-founder of SideQuests Travel. I created SideQuests because I didn't want to just see the world, I wanted to make new friends and build-up my community while doing it. I wanted to see an amazing place in the world and come home feeling changed, so I started hosting trips for people who wanted the same.
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SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.
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The moment you book, you're added to the trip's WhatsApp chat and invited to our monthly Zoom calls, so by the time you land, you already know a bit about each person embarking on the adventure with you. On most group tours, you finally click with the others right as everyone packs to leave,
but on our trips, that happens before anyone boards a plane.
We offer optional journal prompts and meditations for those that would like to participate, and a community workshop mid-trip where people share stories and truly get the opportunity to connect on a very real level.
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SideQuests Travel is for everyone who wants a fun, community-focused tour that’s adventurous, welcoming, and transformative.
Every hotel, guide, and operator is vetted through an LGBTQ+ lens ensuring that travel is not only safe, but enthusiastically welcoming.
Come solo, come with a friend, or a partner, and leave with a new group of friends and strengthened sense of community. We're not just building great experiences, we're building a supportive network of people you'll literally want to plan your next trip alongside.
Where You’ll Stay
Where you stay is part of the experience, so we've picked two boutique hotels with real character and put you right where the action is. You'll spend your first night in Portland at Jupiter NEXT, then three nights in Bend at the Campfire Hotel, our home base for the festival weekend. Both are central, comfortable, and walkable to great food and drinks. Rooms are double occupancy, with private rooms available, and all lodging taxes are included in your trip price.
Jupiter NEXT — Portland (1 night) A stylish, modern boutique hotel on Portland's vibrant east side, walkable to bars, restaurants, and coffee. Our comfortable home base for the first night before we head to the mountains.
Campfire Hotel — Bend (3 nights) A retro-cool basecamp in the heart of Bend with a heated outdoor pool and hot tub, right in the middle of the Winter PrideFest action. Our home for the festival weekend.
All accommodations feature private bathrooms. Solo travelers can choose between shared rooms (with another solo traveler, partner or friend), or a completely private room for an additional supplement. If a friend or partner is coming with you but booking separately, no need to worry... we send out a questionnaire to get your roommate of choice or rooming preferences in order ahead of the trip.
Testimonials From Our Travelers
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![A man with tattoos and earrings standing at the beach during sunset, looking to his left.]()
“We felt like family just a day or two into the actual trip.”
David, Greece
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![A man standing on a sandy beach during sunset, smiling and looking to his right, wearing a pink short-sleeve shirt with a white leaf pattern.]()
"It’s wild how quickly a group of queer travelers became a little family. From late-night laughs to deep conversations, this trip gave me so much more than I expected."
JJ, Costa Rica
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![Two smiling men, one with blond hair and the other with brown hair and glasses, standing close together with their arms around each other, in front of a decorated building with colorful architecture.]()
"I’ve already signed up for three more trips! I’ve never felt more welcome in a group setting."
David, Thailand
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![Three young men standing on the beach with ocean in the background, smiling and enjoying the moment.]()
"He made sure everyone felt included and was enjoying themselves... He checked in with everyone to make sure we were all onboard with our schedules and feeling good about the trip overall.”
Thomas, Greece
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![A smiling man with dark, wavy hair and a beard, wearing a white shirt, standing in front of a stone wall during sunset.]()
"Matthew created an environment welcoming and safe for everyone (regardless of gender identity or sexuality) to have an amazing trip.”
Sam, Greece
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“Michael and Matt were great at breaking down barriers and helping all feel welcome.”
Kevin, Costa Rica
