Sip, Shop, Stay and Play in historic Oakland, Oregon
Image and blog post by OED member Alysha Sanford Photo & Marketing
If you're planning a road trip through Southern Oregon, consider making Oakland, Oregon your restful base for discovery. With quaint charm, walk-able streets lined with history, and a growing community of exceptional small businesses, Oakland offers just enough to enchant and serves as a perfect springboard to waterfalls, vineyards, the Oregon Coast, Crater Lake, and more.
While in town, let your itinerary revolve around four inviting pillars: Sip, Shop, Stay and Play. Below is a curated guide to making the most of your stay in historic Oakland—plus inspiration for day trips that extend your exploration far beyond our borders.
Sip in historic Oakland, Oregon
Begin your day (or wrap up your afternoon) in local flavor. As one of our Oakland Economic Development members, Oakland Coffee Co. shares space with fellow OED member Triple Oak Wine Vault and serves fresh coffee, teas, and treats. It’s a perfect spot to linger and soak in small-town vibes.
When you’re ready for something stronger, stop in at Lamplighter Café & Lounge—another dedicated OED member—offering full meals, a bar, and a place to unwind after a day of exploring.
And for wine lovers, Triple Oak Wine Vault (also a member) brings award-winning estate wines right in historic downtown. You can pair your stroll through town with a tasting experience just moments away.
These spots do more than just pour drinks—they connect you to the heartbeat of Oakland.
Additional sips and eats are available for you to explore and are listed here.
Shop in historic Oakland, Oregon
Oakland’s downtown is a treasure trove of character, lined with vintage storefronts and brick façades. As you wander, explore OED member businesses like:
Olde Town Antiques — curated vintage finds and artistry in the heart of Locust Street
Oakland Flour Mill Antiques & Gifts — a multi-vendor space filled with unique goods
Additional shops are available for you to explore and are listed here.
Stay in historic Oakland, Oregon
Oakland offers lodging options that feel like home, with a touch of local personality:
The Wine Room Airbnb — tucked behind Triple Oak Wine Vault downtown, with thoughtful modern touches
The Ranch Motel — mid-century a-frames, welcoming, and convenient for road travelers just 10 miles north of downtown Oakland, Oregon
Mildred Kanipe Memorial Park — 15 equestrian campsites with corrals and 5 non-horse camp sites about 10 miles northeast of downtown Oakland, Oregon for the camping enthusiasts
Staying a few nights lets you relax into Oakland’s slower pace, revisit favorite spots, and venture farther afield without rushing.
Additional stays are available for you to explore and are listed here.
Play in historic Oakland, Oregon and Beyond
In Town
Visit the Oakland Museum to explore local artifacts, stories, and exhibitions
Spend the afternoon at Mildred Kanipe Memorial Park to enjoy a picnic area with roaming peacocks, equestrian trails for day-riding & hiking, 15 equestrian campsites with corrals and 5 non-horse camp sites
Watch for our annual vintage street fair, ghost tour, wine walk, cookie crawl and more, all listed on our OED Events page
Day Trips & Regional Wonders
Oakland is a strategic launch point to explore the beauty of Oregon:
Discover nearby waterfalls nestled in forested hillsides
Head west to the Oregon Coast for dramatic shoreline and ocean air
Venture east toward Crater Lake and soak in the Cascades’ high-country splendor
Drive through the Umpqua Valley wine country, forested byways, and scenic overlooks
Use Oakland as your base camp—with a comfortable bed, good food, and cozy charm—while the region opens up in every direction.
Additional ways to play are available for you to explore and are listed here.
A Community Rooted in History and Ready to Welcome You
Oakland isn’t just another dot on the map. It’s a place where stories are preserved, creativity thrives, and the people behind each storefront, sip, and smile are deeply invested in what they do. From restored historic buildings to lovingly curated shops and menus, the care that goes into this town is visible at every turn.
This is a community that honors its past while building toward a vibrant future, one handcrafted business at a time. Our small business owners are passionate locals, proud to share Oakland’s legacy with visitors, neighbors, and newcomers alike. Whether you’re here for a morning stroll or a multi-day adventure, you’ll find a town eager to make space for you, your family, and your curiosity.
So come for the charm, stay for the conversations, and leave with new favorite places you'll want to return to again and again. We can't wait to share the heart of historic Oakland with you!