All Aboard!

Orchardist and new railroad owner gets agritourism on track for expansion

Story and photos by Drew Myron

From fruit to freight, Scott Webster is growing possibilities in Hood River Valley.

Like a youngster with a new toy, Scott Webster admires the freshly painted and gleaming Mount Hood Railroad locomotive. After years of turmoil, the beloved short-line railroad is back on track and powered by local ownership, including Scott.

Considered one of the nation’s top scenic railroads, the century-old train has long chugged the route along the Hood River and through the orchards of the verdant valley that open up to offer picturesque views of Oregon’s tallest peak.

Built in 1906, Mount Hood Railroad is a 22-mile line that once carried fruit and forest products and served as an economic lifeline for Hood River Valley. As industry switched to truck transportation, loads grew lighter, and Union Pacific threatened to abandon the line.

In 1987, a group of 20 local investors bought the railroad from Union Pacific and started passenger excursions to supplement the freight business.

In 2008, the railroad was sold to a company based in Chicago. However, the owners defaulted on a loan that ballooned into a $28 million debt. The railroad was placed into receivership—a form of bankruptcy protection providing time to resolve financial obligations.

Pandemic restrictions shuttered passenger excursions, then it operated with limited runs. The swell of changes frustrated many, including Parkdale shop owners who had relied on train traffic to boost business.

Now, after years of upheaval, Mount Hood Railroad is back on track. Scott, an orchardist and entrepreneur, joined with 2 local investors—including Ron Kaufman, the railroad’s longtime general manager—and bought the railroad in December 2021.

“Buying the railroad is one of the most exciting things in my career,” says Scott, who serves as primary investor.

Scott also owns Webster Orchards, with 1,000 acres throughout the Gorge; and The Fruit Company, a multimillion-dollar online retailer shipping 450,000 fresh fruit and gourmet gifts annually.

The combined companies employ more than 500 people throughout the year. Webster Orchards was founded 80 years ago by Scott’s grandparents, Roy and Olive Webster. They later passed it on to their son, Wayne.

At The Fruit Company in Pine Grove, employees sort, pack and ship more than 400,000 fruit and gift packages each year.

Scott and his brother, Addison, bought the company in the late 1990s. In 1999, at the advent of online marketing, they created The Fruit Company to directly use the fruit their orchards produced.

Addison has since left the company, and Scott is sole owner.

In 2003, the company earned praise from Oprah Winfrey’s O magazine, and continues to rank among the nation’s best fruit basket businesses.

The Fruit Company is headquartered in a 160,000-square-foot factory on Van Horn Drive along the railroad tracks in Pine Grove. The historic building formerly served as a cold storage facility owned by Diamond Fruit Growers.

While some freight shipping continues, the railroad’s primary revenue is generated from passenger excursions.

Scott sees The Fruit Company as the anchor business driving a major expansion of agritourism in Hood River Valley.

“We want to create experiences,” he says. “We want people to experience the agricultural history, fruits and beauty of the area.”

The first experience—railbike excursions— kicked off last summer. Using the existing rail, tandem railbikes travel 5 miles along forest, river and orchards. Riders can pedal or use an electric-assist option, allowing all ages and abilities to participate. In the first season, 1,800 people rode the rails.

The ride includes a stop at The Fruit Company’s gift shop and heritage museum, another experience created last summer. Located at the company headquarters, a portion of the 1940s-era building has been converted into a sophisticated nod to the past, with photos and displays that honor the legacy of Roy Webster and other early Hood River Valley growers.

The third experience is a renovation of the Mt. Hood train depot in downtown Hood River. The historic building is getting a cosmetic update with a new gift shop, exterior lighting and signage.

“I applaud his enthusiasm,” says Steve Bickford, owner of Mt. Hood Winery. “I think Scott’s a visionary.”

Neighbor to The Fruit Company, the award-winning winery is itself a pioneer in agritourism. For generations, the Bickford family grew apples and pears before turning to grapes 20 years ago and creating one of the valley’s first wineries.

Scott would like to see a train depot at the historic Pine Grove factory, allowing for shorter train excursions that travel from Pine Grove to Hood River or Pine Grove to Parkdale.

“People don’t want to do 3-and-a- half- to 4-hour trips anymore,” says Scott of the traditional Hood River to Parkdale excursion. “The new generation wants things quick.”

Scott Webster, owner of The Fruit Company, bought Mount Hood Railroad with two investors to bring life back to a vital piece of history.

Already the new summer train excursion has been made into a 2-and-a-half hour trip that departs from downtown Hood River and travels along the lower  fork of the Hood River, with a stop at The Fruit Company’s gift shop and museum. The Christmas Train, a seasonal family favorite, is a one-hour adventure that journeys from Hood River to Pine Grove and back.

“We absolutely see the train coming back to Parkdale,” says Scott, who is working to resolve permit issues with the county. “But we want it to leave from here in Pine Grove.”

With The Fruit Company as home base, additional plans include factory tours, guided orchard and vineyard tours, electric bike rentals and helicopter tours.

“It’s a big dream, but we’re accomplishing many parts of it,” Scott says. “It’s all about the experience, one-on-one with the customer, face to face.”