Ski & Snowboard Trip

4 days, 3 nights of mountain adventures in the snow.

Pray for snow.

Gather the boyz and let’s go ride some snowy volcanic peaks here in Central Oregon. The terrain is super playful and fun, great for skier and boarders. And the backcountry options can be safe and mellow. We can ski just at the resort, or check into the backcountry (or a little bit of both), it’s up to your crew and whatever Mother Nature sends our way. This does include two lift tickets per person to Mt Bachelor, so either way we will get two full days of riding in. We’ll also have bonfires, sample local grub & grog, soak in a bath house, and even go on a headlamp snowshoe to a warming hut for dinner. It’s got the recipe for a pretty legendary trip, we’ll just have to roll the dice on the fresh snow.

4 days, 3 nights, all-inclusive (besides your ski/board rental, byo if can). This trip is reserved for intermediate to advanced riders.

LOCATION:

Bend, OR

TRIP LENGTH:

4 days

ACCOMMODATIONS:

Glamping

GROUP SIZE:

3-4 guys

PER PERSON:

$1,600

ANYTIME:

Jan - Apr

A snowboarder in yellow pants and a dark jacket making a turn on a snow-covered slope, kicking up a trail of snow behind them.
Indoor pool with a fountain in the center, surrounded by colorful mosaic walls and turquoise tiles, with lion statues at the pool's edge.
Snow-covered mountain with a forest of pine trees at the base, under a clear sky at sunset.

Here’s the idea…

Your crew will fly into Bend, OR and it’ll be my pleasure to host you and show you around town, it’s incredible eateries and breweries, and it’s snow covered peaks.

We’ll stay at my Outfitter Shop (roughing it a little), hit the snow each day, enjoy raging warming fires, great food and even a snowshoe to a warming hut deep in the forest (by headlamp or moonlight). We’ll also hit a magical Turkish soaking pool after a long day of snow play.

I’ll also show you some hidden gems along the way. There’s adventure and beauty around every corder up here in Oregon. You’re gonna love it.

Trip Features:

  • Indoor pool with a fountain in the center, surrounded by turquoise tiles, statues of lions at the edges, and colorful mosaic murals on the walls.

    A warm soak after a few snowy days is pure magic.

  • People snowshoeing on a snowy trail through winter forest.

    Safe terrain for a good introductory to the backcountry experience.

  • A plate of tacos with ground meat, chopped onions, and lime, held in front of a snowy outdoor setting with people and parked cars, with a can of Lagunitas pub beer in the foreground.

    Parking lot hang, drinks, warming fire and elk tacos.

  • Snow-covered forest with tall trees, a small cabin with snow on its roof, a lit campfire, and a snow-covered ground with tracks.

    Warming hut dinner & drinks in a wintery wonderland.

  • Snow-covered mountain with a forest at the base, under a clear blue sky during sunset or sunrise.

    Ski/Ride the famously fun Mt Bachelor in sunny Central Oregon.

  • Outdoor grilling scene with steaks, chopped onions, and yellow bell peppers cooking over a grill with a fire. A person is slicing vegetables on a cutting board nearby.

    Good grub is a must. We will cook a few meals, and we'll eat out a few meals.

  • A cozy cabin living room with two brown leather sofas, a wood stove with a fire, a rustic wooden coffee table, mounted animal skull with antlers, outdoor gear, and a ping pong table.

    Crash in comfort. Welcome to glamping - winter edition. It's only kinda roughin' it.

  • People gathered outdoors in winter, standing around a fire pit, with snow on the ground and buildings, and decorative Christmas lights hanging overhead during evening.

    A night out - this town has an infinite amount of warming fires and breweries.

  • A skier in an orange jacket and black pants skiing through fresh snow in a winter forest with snow-covered trees.

    Good quality snow is what this place is known for. The high desert delivers!

GALLERY

The types of things you’ll see & experience:

A person hiking in a snowy mountain landscape with snow-covered trees and mountain peaks in the background.
Indoor spa with a small pool, central fountain, decorative lion statues, and ornate murals on the wall.
A wooden snowboard with green bindings standing upright in the snow in a forest with snow-covered trees.
Two people are skiing on a snowy landscape with a large snow-covered mountain, possibly a volcano, in the background under a clear blue sky.
Outdoor grilling scene with salmon fillet, seared beef patties, sliced onions, and lemon slices on a grill over open flames. A person using tongs to handle the food, with snack cans and cutting boards nearby.
A cozy rustic living room with wooden walls and ceiling, a wood stove with a fire inside, and a mounted deer skull with antlers on the wall. There are two leather sofas, a wooden coffee table, and various sports equipment and decor items, including a
A dog sleeping on a cushion in front of a wood stove with a fire burning inside, in a rustic wood-paneled room.
Three men gathered around a campfire at night, with dark sky and clouds in the background. One man is sitting and the other two are standing, all dressed warmly.
A person in winter gear, including a striped beanie and ski goggles, standing in a snowy landscape with snow-covered trees and mountains, holding a snowboard.
Snow-covered trees and a person skiing in a winter forest with mountains in the background under a blue sky.
A person skiing through a snowy forest with snow-covered trees and clear blue sky.
A plate with tacos topped with ground meat and chopped onions, lime wedges, and a can of pub beer, with people gathered outdoors in a snowy environment near parked cars and coniferous trees in the background.
People gathered outside around a fire pit during winter evening, with snow on the ground and trees, with buildings and string lights in the background.
A person skiing uphill in snowy mountain terrain with trees and ski tracks, under a partly cloudy sky.
A person snowboarding on a snowy mountain slope with snow-covered trees, with snow-capped mountains and blue sky in the background.
Two people skiing through snow-covered forest with tall evergreen trees.
Snow-covered forest with tall trees and a small wooden shelter with a snow-covered roof. A campfire is burning outside, and there are footprints in the snow around the shelter.
Person holding a can of Sierra Nevada beer outdoors in snowy mountain landscape with a log cabin and a person in a bright yellow jacket in the background.
People hiking in a snow-covered forest at night with headlamps, under a starry sky.

The Details:

All-Inclusive: I’ll take care of all the essentials (ground transportation, food, drinks, lodging and lift tickets) so all you guys have to do is say ‘yes!’ and get to Bend, OR with your snow gear.

Group Size: 3 - 4 guys

Duration: 4 days / 3 Nights

Where: Trip departs from Bend, Oregon. Fly into Redmond Municipal Airport (RDM) nearest airport

Experience Level: Some previous skiing/riding experience is needed for this trip, especially if you’re interested in getting into the backcountry (if the conditions allow). The plan is do one resort day and one day that is intro-level backcountry, but again, we’ll see what the conditions allow. Each rider gets at least 2 days of resort access. So no matter what we’ll be up there having fun in the snow. We’ll be riding mainly blue square and black diamond type of terrain, park options, and you will need to be able to handle any variable conditions that mother nature gives us (from blowing sideways snow, to less than ideal icy conditions). We won’t know what kind of skiing day we’ll get until the day of. We’ll have to go with the flow, and make the most of whatever we get!


Dates:

Anytime January - April (whatever dates work best for your crew of guys). Those months generally provide the best opportunity for a good base and best chances for new snow.

Itinerary:

Nature goes with the flow - so do we.

Although I do my very best to adhere to the general schedule, the itinerary is subject to change for numerous reasons beyond my control.

    • For those can arrive early we can go pickup any rental gear that you need

    • If you brought your own gear (which is preferred), we can wax boards/skis in the shop if needed

    • Welcome dinner, local brews and a raging bonfire outside

    • Start a warming fire in the shop and get some rest

    • Coffee and breakfast burrito in hand we’ll head up to the ski hill early (can rent gear up there if needed)

    • Ride all morning

    • Parking lot lunch (elk tacos), drinks and a propane warming fire

    • Afternoon laps until your legs are dead or until last chair

    • Local brewery downtown for dinner

    • Shop hang for games and a night cap

    • Coffee & Breakfast

    • Early morning up to the mountain, or we can check into the backcountry if available

    • Parking lot hot lunch, drinks and a propane warming fire

    • Afternoon we’ll do a soaking mineral pool (Turkish Bath style) in town

    • Snowshoe to a warming hut for dinner

    • Headlamp hike out in the dark

    • Shop hang and night cap

  • Three options if time allows before departure:

    1. Either a slow morning with coffee and breakfast

    2. Or if the conditions and time allows we can do a quick sunrise backcountry mission

    3. Late morning soaking pool if we haven’t done it yet

    • Shuttle run to the airport around/after lunch

Price: $1,600 per person

Included:

  • Two lift tickets per person giving you full access to our legendary local ski hill - the incredibly fun and playful Mt Bachelor.

  • All meals, snacks and drinks - from dinner on Day 1 to breakfast on Day 4

  • 3 nights lodging in my Outfitter shop on cots, futons or couches (only kinda roughing it - heated by wood stove - nice and cozy), local transportation, airport shuttle, conversations that matter, and daily wellbeing practices.

Not included:

  • Getting to/from Bend, Oregon (Drive or fly - airport code: RDM)

  • Gear rental (downhill and/or backcountry), you can easily rent gear in town or up at the mtn

  • If you want to upgrade to a snowmobile for the backcountry day, that’s doable but we’ll need to rent a few sleds which is an additional $250 per person

  • If you’d rather stay in a boutique hotel downtown, where it’s all walkable, add roughly $250 per person

Add-ons & Upgrades:

  • A person wearing a blue jacket, orange pants, white helmet, and green ski goggles skiing downhill on a snow-covered slope under a clear blue sky.

    FAST TRACK (no lift lines): +$100 pp

  • Person riding a Polaris snowmobile on snowy terrain with another snowmobile in the background during daylight.

    SLEDS: +$250 pp

  • A collection of skis, snowboards, and ski poles stored against a wall in a ski room.

    RENTAL GEAR: +$100-250 pp

  • A cozy hotel room with wood-paneled walls, two beds with patterned pillows and throws, a window with curtains, a wall-mounted television, and a small window above one bed.

    BOUTIQUE HOTEL: +$250 pp

Ride or die.

Reserve your group’s ski trip by paying the deposit. First come first served.

Reserve (pay group trip deposit)

What other men are saying:

A grayscale portrait of a man with short, styled hair and a serious expression

Talk about a life tonic for the soul. I’ve lived better because of my time with Gary. Forever grateful.

— Anders Lindwall, Film Maker

Young man smiling, wearing a cap that says 'Explore More' in a casual outdoor setting

Gary’s passion for adventure and connecting with others creates an ideal environment for an unforgettable and transformational trip.

— Mike Day, Teacher

A man with a beard wearing a cap that says '10 Barrel Brewing Co.'

Gary’s heart was made for adventure. He perfectly balances stoke, planning and preparation, and being off the grid with self discovery, camaraderie, and connecting with that part of your soul that longs for adventure.

— Casey Thompson, Executive Consultant

Person wearing a beanie in a body of water, surrounded by other people taking photos.

Spending time with Gary always leaves me feeling hopeful and inspired. He’s a positive, upbeat man with a wonderful outlook on life and a deep connection to the natural world. We all can use more of that energy in our lives.

— Josh Solar, Creative Entrepreneur