The (Oak)land of Opportunities

This quaint historic town is poised to be a popular wine destination

By Dr. Rachel Schelble

Nestled just two miles from the bustling I-5 corridor, Oakland is a charming town that feels like a snapshot from a bygone era. Founded in 1872 with the arrival of the railroad, the historic downtown area exudes a nostalgic allure captivating visitors from near and far. This quaint community is especially appealing to wine enthusiasts, featuring three inviting wine-tasting rooms, making it a fantastic destination for those eager to explore a variety of wines.

Among these is the newest addition, family-owned and operated Oakland Creek Vineyards, located alongside the Triple Oak Wine Vault. Together, these two tasting rooms share the charming E.G. Young and Company building, a brick and stone structure built in 1892 that once served as both a bank and general mercantile. As Oakland began to flourish and change over the years, this historic building became a cornerstone of the community, standing as a symbol of stability and dedication to its customers, leaving an indelible mark on Oakland’s financial legacy.

Just a short stroll around the corner from the tasting rooms lies The Secret Wine Society, known for its extensive wine collection and knowledgeable staff. Here, every visitor can find a special bottle satisfying their personal tastes, enhancing Oakland’s reputation as a wine lover's haven. Constructed in 1891, the brick building was originally known as the Palace Saloon, managed by the Crouch Brothers.

Despite its rich history and vibrant offerings, Oakland's true potential and ongoing revitalization are only beginning to unfold. Several historic buildings are currently on the market, presenting exciting investment opportunities for those looking to contribute to the town's growth and transformation. Whether you’re seeking a unique getaway or an enticing business venture, Oakland warmly invites you to uncover its hidden treasures and become part of its evolving story.

Stearns Hardware: A Pillar of the Community

Since its founding in 1887, Stearns Hardware has stood as a pillar of downtown Oakland, nurturing deep connections with the local community and proudly serving as the town's sole mercantile. Established in partnership with the Chenoweth family, the store opened nine years after Oakland’s incorporation and has remained family-owned and operated for over 130 years, creating a rich legacy that resonates through the generations.

The historic building that houses Stearns Hardware was constructed by George Stearns in 1891, showcasing the exceptional craftsmanship of its era with its classic brick masonry façade. This architectural gem, located at the corner of Locust and Second Streets, continues to be owned by the Stearns family, embodying the enduring spirit and heritage of Oakland. Recognized as a primary contributing property in the Oakland Historic District, the building was added to the National Register of Historic Places in 1979, allowing it to celebrate both its historical significance and its role in modern business.

Today, Stearns Hardware retains its historic charm, seamlessly blending the past with contemporary business needs. Serving not only the 920 residents of Oakland but also the surrounding rural area, it is the heart of the community, providing essential goods and services to neighbors near and far.

To acquire Stearns Hardware is more than merely an investment; it represents a chance to uphold a proud tradition of service and camaraderie within this tight-knit community. With the seller offering support during the transition and the promise of excellent foot traffic along the main commercial street, this historic hardware store stands as a rewarding venture and an invitation to become an integral part of Oakland’s storied history. For those seeking to embrace the spirit of entrepreneurship in a warm and welcoming environment, Stearns Hardware is a must-see opportunity.

The store’s main entrance is flanked by display windows, providing ample opportunity for seasonal displays to catch the eye of passing customers. Inside, prospective owners will find an array of shelving, counters, equipment, and an antique safe— all included in this rare turnkey business opportunity.

The Enduring Legacy of Tolly’s Restaurant

Tolly’s restaurant carries with it a rich history that has endeared it to the community for over 50 years. The journey began in 1968 when Terry and Carol Tollefson purchased the building alongside their friends Don and Erma Mode. The Tollefsons transformed the space into Tolly’s, focusing initially on sandwiches and later introducing a charming soda fountain.

The historic brick building, located on Locust Street, was built in 1903 by Charles and Pitzer Beckley, the sons of Oregon immigrants. Emerged after the devastating Oakland Fire of 1899, it was originally designed as a general merchandise store and drug store. The building pays tribute to the exquisite craftsmanship of its era, featuring decorative elements and antique details, contributing to its unique ambiance.

Known for its diverse and delicious menu, Tolly’s delighted diners with everything from Reuben sandwiches and ribeye steaks to an impressive dessert selection that included pies, cakes and ice cream. The restaurant’s eclectic décor further enhanced the dining experience, merging elements of a restaurant with those of a museum. Antique wood drawers, whimsical antlers above the bar, and a captivating staircase crowned by a carousel horse tell the story of the past, and the iconic soda fountain with its swivel counter stools was a cherished feature.

In its heyday, Tolly’s earned recognition as an Oregon culinary landmark, attracting over 150,000 visitors annually. This influx of tourists was a testament to the vibrant atmosphere and the welcoming spirit of the community, which always embraced the restaurant. In 2001, the Tollefsons sold Tolly’s, setting in motion a series of ownership changes. Despite these transitions, the restaurant’s legacy remains woven into the fabric of Oakland, a testament to its role as a cherished local establishment, historic landmark and a beloved part of many residents’ lives.

Oakland’s Renaissance

Beyond Stearns Hardware and Tolly’s, Oakland boasts a selection of historic buildings for sale, each brimming with immense potential for revitalization and development.

Among these treasures is the Thomas Hotel, constructed by Richard and Sarah Thomas after the town’s destructive 1899 fire. Once the most popular of six hotels in the area, this landmark embodies the town’s rich history and offers opportunities for a new chapter.

At 110 and 116 Locust Street are two iconic structures originally established by Jeptha Grubbe in 1899 and 1900. The building at 110 Locust Street has a fascinating past, having served as a saloon and barbershop before transforming into a furniture store, tavern, ballet studio and an antique shop. Its versatile history makes it a compelling option for a variety of modern uses.

Next door, the brick structure at 116 Locust Street presents incredible possibilities with two storefronts. This historically significant building originally housed a confectionery store and real estate office, later becoming a restaurant, deli and wine business, printing shop and, most recently, an antique store. With its prime location and diverse history, this property stands ready for new ventures waiting to be realized.

As Oakland continues to evolve, these historic buildings represent unique opportunities for investment and innovation, inviting visionaries to contribute to the town's ongoing renaissance.

Dr. Rachel Schelble is a passionate entrepreneur and dedicated community leader who founded Oakland Creek Vineyards in Oakland, Oregon, in 2022. With a vision to create a welcoming space for wine enthusiasts, Rachel and her family opened a new tasting room located in the historic E.G. Young and Company Bank Building, which was built in 1892. This charming tasting room not only celebrates the rich heritage of the area but also aims to foster connections within the community.

Her passion for connecting people through the shared experience of enjoying wine reflects her belief in the power of community and the importance of preserving the natural beauty of the Umpqua Valley.

In addition to her work at the winery, Rachel is an active participant in local initiatives aimed at enhancing the community's growth and vitality. She regularly engages with local business groups and organizations, providing support and leadership to help promote Oakland as a treasured destination for visitors and residents alike.