Our journey to Central Oregon begins this morning as the van departs the Willamette Valley and heads east over the Cascade Range via Santiam Pass — a scenic corridor of volcanic peaks and high desert vistas that serves as a fitting overture to the days ahead. En route, we stop at a family-owned Central Oregon winery for a midday lunch and wine tasting, enjoying handcrafted small-batch wines with sweeping views of Smith Rock and the Cascade Mountains. Following our tasting, we visit Smith Rock State Park — one of Oregon's most celebrated natural landmarks — for a relaxed walk along the Crooked River Trail, with the towering rock formations rising dramatically above us. Late afternoon brings our arrival at Juniper Preserve, where we settle into our rooms before gathering for a welcome dinner on property.

Stop at a family-owned Central Oregon winery for a midday lunch and wine tasting, enjoying handcrafted small-batch wines with sweeping views of Smith Rock and the Cascade Mountains.

Visit Smith Rock State Park for a relaxed walk along the Crooked River Trail, with the towering rock formations rising dramatically above.

Arrive and check in at Juniper Preserve, Bend, settling into rooms before dinner.

Gather for a welcome dinner on property at Juniper Preserve.

After breakfast at the resort, we make our way south to Newberry National Volcanic Monument, where the raw power of Central Oregon's volcanic history unfolds before us.

At the Lava Lands Visitor Center, we explore accessible trails through remarkable lava formations, including the Trail of Molten Land, where ancient eruptions left behind a landscape that seems almost otherworldly. A knowledgeable ranger brings the geology and natural history of this place to life, offering context that makes the scenery all the more extraordinary.

Our afternoon takes us to the High Desert Museum, one of the Pacific Northwest's most compelling cultural destinations. Part indoor gallery, part outdoor natural history experience, the museum tells the story of the high desert's people, wildlife, and landscape with a depth and artistry that rewards a slow, unhurried visit. River otters, raptors, a recreated 1904 homestead, and a working sawmill are among the highlights — each offering a vivid window into life in this remarkable region. We have time to browse the museum's shop and enjoy a light café lunch before moving on.

The evening takes us into Bend for a group dinner at one of the city's most celebrated restaurants. Bend has grown into a genuine dining destination, and tonight's meal reflects that — thoughtfully sourced ingredients, Pacific Northwest character, and warm hospitality in a setting that feels entirely of this place.

Afterward, the van returns us to Juniper Preserve for a peaceful evening at the resort.

After breakfast, we head west on US-20 toward the charming mountain town of Sisters — and the centerpiece of our journey.

The Annual Sisters Harvest Faire transforms Main Avenue into a vibrant celebration of craft, community, and the season. Juried artisans display handcrafted pottery, jewelry, woodwork, textiles, and more, while live music fills the streets and the golden light of an October morning falls across the Cascade Range behind the town. We arrive before the gates open, giving us the full day to explore at a relaxed, unhurried pace.

The Faire runs through the afternoon, offering ample time to discover the work of artists from across the region, sample offerings from food vendors, and simply soak in the spirit of this beloved Central Oregon community event. Lunch is on your own among the Faire's many food vendors and nearby Sisters restaurants — a pleasant opportunity to explore the town on your own terms. For a group of ten, the executive van format allows complete freedom of movement throughout the day.

Overnight: Juniper Preserve, Bend, OR

Our final morning begins with a leisurely breakfast at Juniper Preserve before we bid farewell to the resort and begin the scenic journey home.

Weather permitting, we make a brief stop at Dee Wright Observatory, a remarkable 1935 lava rock structure perched at the summit of McKenzie Pass, where panoramic views extend across six Cascade peaks on a clear day.

We stop in Sweet Home for a group lunch before completing our journey home to the Willamette Valley.