Posted by Hillcrest Sports on Jun 4th 2026
Five Decades on the Mountain, the Water & the Pavement
Five Decades on the Mountain, the Water & the Pavement
Celebrating 50 years of Hillcrest Sports — Gresham’s original home for every season, every rider, every adventure.
From a Winter Ski Shop to the Northwest’s Greatest Outdoor Outfitter
Fifty years ago, in the winter of 1976, a man named Dexter Hill unlocked the doors of a small ski shop in Gresham, Oregon — and started something that would outlast trends, recessions, and the rise and fall of entire sporting categories. That shop was Hillcrest Sports.
Back then, Gresham was still finding its feet, and Mount Hood was the beating heart of the region’s outdoor culture. Dexter’s vision was simple: give passionate skiers the gear they needed, right here on the east side of Portland, without the drive downtown. In those early years, Hillcrest kept a tight seasonal focus — open through winter, closed through summer — a shop that lived and breathed the mountain.
What nobody could have predicted in 1976 was just how big the story would get.
“Everyone working at Hillcrest is passionate about helping our customers get into the proper gear at a great price so they can have an awesome time shredding the mountain, ripping on the water, or throwing down on the pavement.”
Today, half a century on, Hillcrest Sports stands as one of the most complete outdoor specialty shops in the entire Pacific Northwest — a full-service winter sports headquarters, a thriving skate shop, a summer watersports outfitter, and a lifestyle apparel destination, all under one roof at 2424 SE Burnside Road. The mission hasn’t changed one bit from what Dexter built in 1976: friendly, passionate, expert service and the right gear at the right price.
Fifty Years of Growth
Dexter Hill founds Hillcrest Ski & Sports in Gresham, OR. The shop opens in winter carrying ski gear exclusively — and quickly earns a loyal following among Portland-area mountain lovers.
1985
For nearly a decade, Hillcrest operates as a beloved winter-season shop. When the first snow falls on Hood, Gresham knows exactly where to go.
A bold move: Hillcrest brings Burton Snowboards into the lineup, becoming one of the first Northwest retailers to embrace the snowboard revolution that would reshape winter sports forever.
Hillcrest goes year-round. The shop expands into water skis, skateboards, running gear, and more — transforming from a seasonal ski shop into a true all-season outfitter serving the whole Portland metro area.
2000s
Hillcrest cements its reputation as the east side’s definitive outdoor shop. The skate shop deepens its roots, watersports offerings grow, and generation after generation of riders, skaters, and paddlers call Hillcrest home.
Hillcrest launches online at hillcrestsports.com, bringing competitive pricing and the same expert service to customers across the country — while staying rooted in Gresham.
50 years. One of the Pacific Northwest’s most complete outdoor specialty retailers. Still family-owned, still passionate, still Gresham’s shop.
When Hillcrest Bet on Snowboarding — and Won
The year was 1985. Snowboarding was barely a sport — more of a curiosity, a fringe pursuit for kids who thought skiing was too tame. Most traditional ski shops wanted nothing to do with it. Hillcrest saw things differently.
By bringing Burton Snowboards into the store — at a time when fewer than a thousand U.S. retailers carried the brand — Hillcrest positioned itself at the forefront of what would become the defining winter sport evolution of the 20th century. Within a year, the shop expanded to stay open year-round, adding water skis, skateboards, and a broader range of sporting goods that laid the foundation for everything Hillcrest is today.
That decision in 1985 says everything about how Hillcrest operates: stay close to the riders, listen to the culture, and trust that great gear and genuine passion will always find their people.
Every Season, Every Discipline
From first powder to last wake, Hillcrest has you covered 365 days a year.
Alpine, backcountry & all-mountain skis, boots, bindings, outerwear & accessories. Expert boot fitting with heat molds and custom insoles. Rentals, tunes & full service.
Top brands including Burton — our original 1985 partner. Boards, boots, bindings, and all the soft goods to keep you shredding in style and comfort all season.
Full-service skate: decks, trucks, wheels, bearings, shoes & apparel. Street, park or cruising — we’ve got what you need with zero pretension.
Wakeboards, wake surfers, iSUPs, kayak rentals, life jackets & everything to make every day on the water an epic one.
Swimsuits, street clothing & casual summer apparel from brands that actually live outdoors. Gear that goes from the mountain to the water to the street.
Ski & snowboard tunes, waxes, repairs & mounts. Professional boot fitters on staff. Rental fleet for skis, snowboards, XC, snowshoes, kayaks & SUPs.
More Than a Store — A Gathering Place
Ask anyone who grew up on the east side of Portland about Hillcrest, and you’ll hear the same thing: this wasn’t just a place to buy gear. It was where you got advice from someone who’d actually skied that run, surfed that spot, or ridden that deck. Where you picked up your first skateboard, got your boots fitted before your first season, or found out which local lake was firing on a random Tuesday.
For fifty years, Hillcrest has been staffed by people who don’t just sell outdoor gear — they live it. Every person behind the counter has been a skier, snowboarder, skater, or water sports enthusiast first, and a retailer second. That culture is baked into the DNA of the shop, and it’s the reason customers keep coming back decade after decade.
“Sharing our love of the outdoors in Portland, Oregon since 1976.”
Through all the changes Gresham has seen over half a century, Hillcrest has remained a constant — the place where Hood River kayakers get their SUPs, where Troutdale teenagers get their first skate setup, where Sandy locals prep for the season’s first powder day.
Still Here. Still Passionate. Still Your Shop.
Half a century in, and Hillcrest Sports isn’t slowing down. The outdoor world keeps evolving — new board shapes, new ski technologies, new watersports disciplines, new brands rising out of nowhere — and Hillcrest stays at the front of it, the same way it jumped on snowboarding in 1985 before almost anyone else did.
Whether you’re shopping in-store at 2424 SE Burnside Road or browsing the full selection at hillcrestsports.com, the Hillcrest promise is the same one Dexter Hill made in 1976: honest expertise, genuine passion, and gear that actually gets you out there doing the thing you love.
Here’s to fifty more years on the mountain, the water, and the pavement. From all of us at Hillcrest — thank you for being part of the ride.
Join the Celebration
Stop by the shop or visit us online to see what five decades of outdoor passion looks like. New gear, expert fitting, and the same friendly service since 1976.
Shop Hillcrest Sports →2424 SE Burnside Rd, Gresham, OR 97080 · (503) 665-4455 · Open 7 days a week