Bend Winter PrideFest Gay Group Trip: Portland, Mount Bachelor & Bend, Oregon

5 Days, 4 Nights

March 3rd-7th, 2027

Hosted by Matthew Schueller

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!
Deposit: $488 (just 25% down)

$1,950

2027: Mar 3 - Mar 7
Portland - Bend - Mount Bachelor
Early Bird Discount - Save $100!

Tour Highlights

What’s Included?

Multi-tiered Vietnamese pagoda tower with golden dragon sculptures and red lanterns in Hanoi
Dozens of fishing boats moored at sunset in Ha Long Bay, with karst mountain silhouettes and golden reflections.

Pricing:

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:

Trip Itinerary:

March 3rd - 7th, 2027

Colourful silk lanterns lining a narrow café-lined train track alley in Hanoi's Old Quarter, Vietnam.

Day 1

Welcome to Portland!

Aerial view of terraced rice fields and scattered village homes across lush green mountains in northern Vietnam

Day 2

Over the Mountains: Timberline Lodge, Smith Rock & Bend

Traveler in a conical hat gazing over the Tam Coc river valley and karst peaks in Ninh Binh, Vietnam.

Day 3

Mount Bachelor: Ski, Relax & a Night Snowshoe Under the Stars

Day 4

Festival Finale: Drag, Pool Party, Farewell Dinner & the Dance Party

Traditional cruise boats on turquoise waters surrounded by limestone karst islands in Ha Long Bay, Vietnam.

Day 5

Brunch, Multnomah Falls, Return to Portland & Departures

Meet Your Host

Ryan is a full-time digital nomad and experienced group travel host who has led multi-day trips since 2022. As the founder of Capsule Adventures, a sober travel company, he brings a calm, organized, and deeply thoughtful approach to creating trips that feel smooth, safe, and genuinely meaningful. Passionate about LGBTQ+ community-building, Ryan creates spaces where queer travelers can fully relax, be themselves, and move through the world together. Having traveled to nearly 40 countries, he believes the best travel moments happen in the in-between, the late nights, shared laughter, and unexpected connections. He’s deeply invested in making sure everyone feels taken care of… and of course, he isn’t shy of a little light roasting, and to break out some humor along the way. He's leading SideQuests adventures in 2026 and 2027, including an incredible gay group trip to Peru!

Frequently Asked Questions

Have questions specific to this trip? Here are some common questions about our adventure.

Travel insurance cancellation policy infographic. It shows the process from before trip confirmation, requiring a full refund including deposit, to within 90 days of trip, when all payments are non-refundable. It notes a 25% deposit that is non-refundable, a $100 cancel fee when trip is confirmed, and that 25% of all payments are fully refundable. The policy recommends travel insurance.

About SideQuests Travel

Where You’ll Stay

Across the week, you'll move through three very different homes-away-from-home: a boutique hotel in the heart of Hanoi's Old Quarter, a countryside resort surrounded by rice paddies and mountains, and a private cabin aboard an overnight cruise ship. All are 4- and 5-star, all are available at double occupancy (2 travelers per room) with single rooms available for an added supplement.

All accommodations feature private bathrooms and daily made-to-order breakfast. 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