A conversation at a high school reunion planted an unexpected seed—one that would soon blossom into a journey through the heart of southern Oregon. When our friends, Carl and Cathy, extended a warm invitation to visit them in the historic mining town of Jacksonville, the idea of visiting their patch of the Pacific Northwest began to take root.
Before we knew it, my husband and I found ourselves embarking on our very first Oregon adventure. We arrived ready for new experiences, shaped by our deepening friendship and the sharing of good wine.
Jacksonville, Oregon – A Gold Rush Town, Now a National Historic District
As we walked to downtown Jacksonville for dinner on our first evening, we began to get a sense of its history as our friends shared points of interest along the way.
Although its current population hovers around 2,900, Jacksonville, Oregon, had its heyday in 1851 when gold was discovered at Rich Gulch. For several decades, it flourished, becoming the largest town in the Oregon Territory. When nearby Medford was chosen as a railroad stop, it became a more desirable location for businesses. Its population continued to grow as Jacksonville’s declined.
Fast forward to the 20th century. In 1966, Jacksonville became the first National Historic Landmark District in Oregon. It was listed for having “the state’s most extensive and complete example of a late 19th-century inland commercial mining community.” A total of 98 buildings constructed between 1850 and 1900 have been preserved and maintained.
Take a Trolley Tour
©Belita Paluay/Belitaspace.com
If you visit between June and October, a Narrated History Trolley tour departs several times daily from the Visitor Information Center. It showcases vintage homes, famous landmarks, and gold rush stories.
The Jacksonville Wine Trolley, which visits all eight wineries in the Jacksonville Wine District, also departs from the Visitor Information Center. It runs from May to October, Friday through Sunday, 12 noon to 6:30 pm.
We visited two wineries in the Jacksonville Wine District with our friends: DANCIN Vineyards and Daisy Creek Vineyard.
Other wineries visited by the Trolley include Hummingbird Estate, Rellik Winery, Dos Mariposas Vineyard (& Lavender Farm), and South Stage Cellars.
DANCIN Vineyards: Ballet-Inspired Labels with Rogue Valley Views
On our first full day in southern Oregon, we spent the morning touring DANCIN Vineyards, near Jacksonville. It was a beautiful introduction to the wines of the Rogue Valley.
A load of just-harvested grapes was arriving as we approached the tasting room terrace, where we were to meet Austin Marca, General Manager, to begin our tour and tasting. On the way, we stopped by the tranquil koi pond just below the hillside tasting room and outdoor dining area.
Marca, the son of owners Dan and Cindy, told us the story of the vineyard’s beginnings in 2007, and how they decided to combine their first names to create the name – DANCIN. Cindy’s love of dancing is also reflected in the design of all their labels. They feature an elegant ballet figure whose “wine dress” mirrors the wine’s character and color.
Their first commercial releases came in 2010. By 2017, DANCIN received the “Oregon Winery of the Year” honor from Wine Press Northwest magazine, a sign that this relatively young estate had quickly found its stride.
©Debbra Dunning Brouillette
Beyond the views and the story, DANCIN is also a place to linger over food. The winery’s menu offerings extend beyond simple tasting room nibbles. Artisan brick-oven pizzas are headliners, alongside shareable sides, salads, and house-made desserts.
Harry & David: Orchard Treats and Iconic Gift Baskets
After our morning at DANCIN Vineyards, we drove into Medford to visit Harry & David’s flagship store. It is still very much the heart of the brand’s orchard‑to‑gift‑box story.
The company traces its roots to 1910, when Samuel Rosenberg founded Bear Creek Orchards as a premium fruit business. Today, it remains best known for its fruit and gift baskets, especially its Royal Riviera pears. They were once described by the founders as so big and juicy that you need a spoon.
Most of the brick‑and‑mortar locations closed in 2020, but the Medford store endures. It is joined by a New York outpost and a handful of seasonal pop‑ups.
As we entered, we were tempted to try samples of Moose Munch popcorn. The sweet‑salty mix of popcorn, nuts, and caramel now comes in two dozen flavors. A tasting of several featured Oregon wines was offered in another part of the store.
It’s an easy place to assemble a picnic—cheeses, crackers, chocolates, and those famous pears—for a winery terrace or, in our case, a future lunch stop at Crater Lake, which we’d planned for the last full day of our visit.
Dinner at The Lindsay Lodge: Overlooking the Applegate River
Our first full day in southern Oregon ended with dinner at The Lindsay Lodge’s restaurant. It is located between Grants Pass and Medford near Jacksonville and overlooks the Applegate River.
The rustic lodge, built with hand-skinned pine, fir, and redwood logs, originally opened in 1992 as Applegate River Lodge. In 2023, it was reopened under new ownership as Lindsay Lodge and Restaurant. Lindsay Applegate, a pioneer of the Applegate Trail, inspired the name.
Irvine & Roberts Vineyard: A Memorable Vineyard to Table Experience
©Debbra Dunning Brouillette
On our second full day in southern Oregon, we headed 15 miles south of Jacksonville to Irvine & Roberts Vineyard, in the foothills of Ashland, within the Rogue Valley AVA.
Upon our arrival, Dionne Irvine, the owner, met us for a tour of the area where they were processing grapes. We saw the sorting, de-stemming, and crushing process, and learned about the varieties the winery produces.
©Debbra Dunning Brouillette
They include estate-grown Pinot Noir, Chardonnay, Pinot Meunier, and Gamay Noir. They were making a Rosé of Pinot Noir (my favorite) on the day we visited. Three distinct sparkling wines are also available here.
Next, we were seated in the tasting room for a special Vineyard to Table experience. Three wines — a Chardonnay, a Pinot Noir, and a Gamay — were paired with three courses (Harvest Panzanella Salad, Flat Iron Steak, and Triple Chocolate Tart). Visitors to the winery can also book two-hour tasting exploration and curated pairing experiences.
©Debbra Dunning Brouillette
In 2025, Irvine & Roberts was ranked #7 on USA TODAY’s 10Best Readers’ Choice Awards list for Best Wine Tasting Room. This national honor highlights both the wines and the hospitality experience.
Daisy Creek Vineyard: Neighborhood Winery with Feel-Good Vibes
By late afternoon, we headed back to Jacksonville. Our next stop was Daisy Creek Vineyard, Carl and Cathy’s favorite local winery. They often come to enjoy live music on the patio, as we did, while sipping a glass of wine. I chose a light, crisp Rosé made from Syrah grapes.
The boutique vineyard is named after the meandering stream that runs through the property from its source high in the mineral-rich Siskiyou Mountains to its end in the Rogue River. Seven acres of grapevines grow eight different varietals. Most are Rhone varieties, including Viognier, Chardonnay, Marsanne, Malbec, Petit Verdot, Tempranillo, Sangiovese, and Syrah.
Crater Lake National Park: Deep Blue Wonder at the Caldera’s Edge
A day trip to Crater Lake National Park was on the agenda for our third day in southern Oregon. It is one of America’s oldest national parks, established in 1902 by President Theodore Roosevelt.
About two hours after leaving Jacksonville, we reached Rim Village, the central hub for visitors exploring the south rim. Before beginning our drive around the lake’s rim, we watched a short video at the Visitors Center. Then we walked through the Crater Lake Lodge, a national historic landmark built in 1915.
Would you rather leave the driving to someone else? Trolley tours of the 33-mile Rim Drive are offered daily from July through mid-September. A ranger on board provides narration, as the tour stops at several overlooks along the way.
We followed a short section of the Rim Trail, pulling over at almost every overlook to take photos and marvel at the lake’s deep blue hues. Later, we found a picnic area to stop for lunch. We unpacked the picnic basket filled with Harry & David cheeses, crackers, and other snacks, and uncorked a bottle of an Oregon rosé.
Kriselle Cellars: Raising a Glass to Friendship and to Southern Oregon
©Debbra Dunning Brouillette
Kriselle Cellars, a hillside estate winery near White City, was the ideal spot to end our four-night visit with friends in Jacksonville. It was named after co-owner/winemaker Scott Steingraber’s wife, Krisell, with an extra “e” added for easier pronunciation.
We were seated on the patio for a tasting and light lunch, overlooking part of the 200-acre ranch’s 25 acres of planted grapes between the Rogue River and Upper Table Rock. Much of the vineyard is dedicated to robust red varieties — Cabernet Sauvignon, Cabernet Franc, and Tempranillo — with small quantities of Malbec, Sangiovese, Viognier, and Sauvignon Blanc.
©Debbra Dunning Brouillette
Before sharing flights of red and white wines, paired with charcuterie, we sampled the daily special — beet wontons. They were paired with Kriselle’s award-winning 2022 Di’Tani, a blend of Cabernet Franc, Cabernet Sauvignon, Malbec, and Tempranillo is a previous winner of the San Francisco Chronicle Wine Competition.
Southern Oregon: Now, It’s More Than a Place on the Map
In the space of a few days, southern Oregon shifted from a place on the map to a place that now feels woven into our own story. Thanks to generous friends, walkable historic streets, the hospitality of its winery owners, and a landscape that constantly invited us to look a little closer, this first Oregon adventure is unlikely to be our last.
If You Go
Direct flights into Rogue Valley International-Medford Airport are available from 10 airports in seven U.S. states. Major connecting hubs with direct flights on American, Delta, United, and Alaska include Phoenix, Portland, San Francisco, and Seattle. Distance from the airport to Jacksonville is eight miles.
Learn more about Jacksonville, including its attractions, art and culture, outdoor adventure, events, and where to eat, drink, and stay: Jacksonville, Oregon
