How to Spend One Week in Southern Oregon: Wine Country, Crater Lake, the Coast & More
I had always wanted to visit Oregon. I had heard so many times how beautiful the state was, but until recently, I had never had the opportunity to experience it for myself.
After spending a week exploring Southern Oregon and the Southern Oregon Coast, I finally understood what everyone had been talking about. The scenery was even more beautiful than I had imagined. But what surprised me just as much was the incredible variety of experiences this region had to offer.
We were fortunate to spend the week with family and friends who live in the area, which gave us an opportunity to experience Southern Oregon almost like locals. We visited places we may never have discovered on our own, met people along the way, and learned so much about this part of Oregon.
Over the course of one week, we toured vineyards and learned about winemaking, visited pear orchards and saw firsthand how important the pear industry is to this region, explored the Southern Oregon Coast, stood above the incredible blue water of Crater Lake, hiked along the Rogue River Gorge, and spent an evening at the Oregon Shakespeare Festival in Ashland. We even followed Highway 101 south along the coast and crossed into Northern California to walk beneath the towering Redwoods.
And there were plenty of moments in between.
One evening, we sat outside at a winery listening to local musician Jeff Kloetzel as the sun went down over the vineyard. We enjoyed wonderful meals, met some of the kindest people, learned about the science behind winemaking, and experienced a sense of community and small-town charm that stayed with me throughout the trip.
Southern Oregon was so much more than I expected—in the very best way.
So, if you're thinking about visiting, here's a look at what makes Southern Oregon worth exploring and how we spent an unforgettable week discovering it.
Why Visit?
Southern Oregon is one of those destinations where you don't have to choose just one type of vacation. Wine country, mountains, rivers, forests, waterfalls, charming towns and the Pacific Coast are all within reach, making it possible to build a trip around several different experiences.
It's also a destination that invites you to explore beyond the places you may already know.
Crater Lake might be one of the region's most recognizable landmarks, but we quickly discovered there was so much more waiting beyond it.
Exploring Southern Oregon Wine Country
Do you love wine? If so, Southern Oregon deserves your attention. This part of the state is home to several wine-growing regions, including the Rogue Valley and Umpqua Valley, both federally recognized American Viticultural Areas (AVAs), along with several smaller AVAs.
The Rogue Valley has also been gaining national recognition as a wine destination. In 2026, it was named the #1 Best Wine Region in the USA TODAY 10BEST Readers' Choice Awards, after placing #2 in 2025 and runner-up in 2024.
What makes this area especially interesting for wine lovers is its variety. Different elevations and microclimates allow growers to produce an impressive range of grapes, including Tempranillo, Syrah, Cabernet Sauvignon, Pinot Noir and Viognier.
During our week, we visited eight wineries, and one thing I quickly learned was that Southern Oregon wine country isn't a single experience. Each winery had its own personality, setting, wines and story.
We visited Belle Fiore Winery, Irvine & Roberts Vineyards, Padigan Winery, Naumes Suncrest Winery, Dunbar Farms Winery, Pebblestone Winery, DANCIN Vineyards, and Red Lily Vineyards. Some visits were about sitting outside with a glass of wine and taking in the vineyard views. Others introduced us to new wines, local music and the people behind them. Everywhere we went, the people were incredibly warm and welcoming. I loved hearing their stories and learning more about their connection to the region and its wine.
One experience that really captured that feeling was our visit to Naumes Suncrest Winery. As we toured the winery, we learned more about the Naumes family and their history in Southern Oregon. A photograph of the parents who founded the family business still hangs on the wall, a wonderful reminder of the generations and family history behind the Naumes name. Hearing their story and seeing that connection to the past made the visit feel incredibly personal. It wasn't simply a stop for a glass of wine—it gave us a glimpse into the people and history behind it.
Another memorable evening was at DANCIN Vineyards, where we had dinner on the patio surrounded by the vineyard. It was also where I tried Sangiovese for the first time—and loved it. Between the wine, dinner, beautiful surroundings and the sunset over the vineyard, it was one of those evenings that reminded me that visiting wine country is about so much more than simply tasting the wine.
Our wine education continued with a special visit to Naumes Crush & Fermentation, a working winemaking facility that isn't open to the public. We were fortunate to have a private tour, and a special thank you goes to Steve, who took so much time walking us through the process and answering our questions. You could immediately tell how much he loved what he did, and his enthusiasm made everything we were learning even more interesting.
We learned about fermentation, how wines develop over time, and some of the decisions that influence what eventually ends up in the bottle. One of the highlights was tasting wine directly from several barrels. As we tasted, Steve helped us understand what we were noticing in each wine, why it tasted the way it did, and how much longer it might remain in the barrel.
I enjoy wine, but before this trip, I had never really understood how much science, timing and decision-making goes into creating what eventually ends up in your glass. Seeing part of that process firsthand gave me an entirely new appreciation for winemaking—and it was a pretty delicious way to learn.
By the end of the week, I left Southern Oregon with a much greater appreciation not only for the wine being produced here, but for the entire wine-country experience—the vineyards, the settings, the stories and especially the people we met along the way.
And because each winery was so different, I'll be sharing a separate guide to the Southern Oregon wineries we visited, including what stood out about each one.
Discovering Southern Oregon's Pear Country
Learning about the pear industry was an unexpected—and interesting—part of our week. The Rogue Valley has a long history of pear growing, dating back more than a century, and pears continue to be an important part of the region's agricultural story today.
Two names that are deeply connected to that story are Naumes, Inc. and Harry & David, and during our week we got a behind-the-scenes look at both.
Our timing couldn't have been better. We visited during harvest season, so both operations were in full swing. At Naumes Packing House, we watched as freshly harvested pears moved through the facility, where they were cleaned, sorted and prepared for fresh markets and specialty orders. Naumes grows several varieties of pears, and seeing the operation firsthand gave me an entirely different perspective on just how much happens between the orchard and the pears we eventually see as consumers.
What fascinated me most was watching the people behind the process. The workers moved incredibly quickly as they sorted and packaged the pears, while at the same time taking such care to make sure the fruit wasn't damaged along the way. We learned that some of the employees have been doing this work for more than 30 years—and still genuinely love what they do. Watching them work and hearing their stories made the experience even more meaningful.
We also toured the Harry & David facility in Medford. I had known the Harry & David name for years, but I had never really thought about its connection to Southern Oregon or the story behind those famous pears.
During the tour, we learned more about their Royal Riviera Pears, known for their sweet, juicy and buttery texture. Again, we were there during harvest season, and able to see the facility in action as the pears were cleaned, sorted and prepared—I'll certainly look at those familiar Harry & David gift boxes a little differently now!
An Overnight on the Southern Oregon Coast in Bandon
After exploring wine country, pear country and the mountains of Southern Oregon, our trip took us west to the coast—and Bandon was everything I hoped an Oregon coastal town would be.
We spent one night there in a house overlooking the Pacific Ocean, and the view alone was incredible. But between the beach, Old Town, great food and a few unexpected moments along the way, Bandon quickly became another favorite stop on our trip.
A Stop at Bandon Dunes
Calling all golf lovers—Bandon Dunes Golf Resort is a destination in itself.
Our first stop was lunch at the resort, where we got our first look at Pacific Dunes, one of seven golf courses that make up Bandon Dunes, including five 18-hole courses and two par-3 courses. I'm not a golfer, but you certainly don't have to play golf to appreciate the setting. With the dramatic Oregon coastline as its backdrop, it was absolutely stunning.
The courses at Bandon Dunes consistently rank among some of the best, and after seeing the property, I could understand why golfers travel from around the world to play here.
A Walk Along the Pacific
After lunch, we dropped off our overnight bags and headed straight for the beach.
I love the ocean, and there is something so peaceful about walking along the shoreline—the sound of the waves, the sand crunching beneath your feet and, of course, searching for the perfect seashell.
We didn't need to be anywhere or do anything. We simply walked, listened to the ocean and enjoyed being there.
Sometimes those are the moments I remember most.
Exploring Old Town Bandon
Later, we made our way into Old Town Bandon, where we spent some time walking around and browsing the shops before dinner.
We stopped at Foley's Irish Pub for a cocktail and ended up meeting owner Noel Foley. We enjoyed talking with him—and listening to that wonderful Irish accent. It was another one of those unplanned interactions that made the trip feel a little more personal.
From there, we headed to Crow's Nest Wheelhouse for dinner. The food was wonderful, but the harbor views made the evening even better. After spending the afternoon along the Pacific, ending the day with dinner overlooking the harbor felt like the perfect way to experience another side of Bandon.
A Quiet Ending to the Day
After dinner, we headed back to the house, poured a glass of wine and took in the ocean views before working on a puzzle.
Yes, a puzzle.
It had been a long time since I had sat down and worked on one, and it was so much fun. There was nowhere else we needed to be and nothing else we needed to fit into the day. We just enjoyed the evening, the view and each other's company.
It was simple—and I loved it.
Bandon also has another claim to fame that I didn't know before our visit: the area has a long history of cranberry growing. Each September, the community celebrates that heritage with the Bandon Cranberry Festival, traditionally held during the second weekend of the month.
Between the dramatic coastline, beautiful beaches, Old Town, harbor and food, Bandon gave us a completely different experience from the other places we visited in Southern Oregon.
Driving Highway 101 to the California Redwoods
As if the ocean views in Bandon weren't beautiful enough, the next morning we headed south along Highway 101, following the Oregon Coast toward Northern California and a place that had been on my bucket list for years—the Redwoods.
What I hadn't anticipated was just how memorable the drive itself would be.
Highway 101 winds along the coast through some incredible scenery. There were dramatic cliffside views, beautiful stretches of beach, winding roads and clouds settling into the mountainsides. Around almost every turn, there seemed to be another reason to look out the window. This was definitely one of those times when the journey was every bit as much a part of the experience as the destination.
Huckleberry Pancakes Along the Way
After crossing into California, we stopped for brunch at the historic Hiouchi Café before heading to the Redwoods.
This was also where I got my first taste of huckleberry pancakes. I hadn't ordered them myself, but after tasting them, I immediately wished I had. They were so good that I spent the rest of the trip looking for something huckleberry to bring home.
A few days later, on our way to Crater Lake, I finally found huckleberry jam and huckleberry honey at Union Creek Resort. Mission accomplished.
Then it was time for the reason we had driven all this way.
Walking Among the Redwoods at Stout Grove
We headed to Stout Grove, where we set out on foot beneath some of the tallest and most incredible trees I had ever seen.
Seeing the Redwoods had been a bucket-list experience for me, but standing beneath them was completely different from seeing them in photographs. Their sheer size is difficult to comprehend until you're walking among them, looking up and trying to see where they end.
We spent our time hiking through the grove, stopping again and again just to take it all in.
And then we came across something completely unexpected—a wedding about to begin among the Redwoods. What an incredible backdrop for such a special day.
I had wanted to see the Redwoods for years, but before this trip, I hadn't realized how easily we could incorporate them into our time in Southern Oregon.
By the time we headed back toward Oregon, I felt like we had experienced three completely different parts of the day—the dramatic Pacific coastline, a classic roadside brunch and the quiet grandeur of standing beneath the Redwoods.
Crater Lake & Rogue River Gorge
Crater Lake was one of those places I had heard about for years and always hoped to see someday. I had seen photographs and knew it was beautiful, but I wasn't prepared for just how spectacular it would be in person.
And as it turned out, Crater Lake wasn't the only highlight of our day. Our stop at Rogue River Gorge was an unexpected surprise.
Our home base for the week was Medford, and even the drive to Crater Lake was beautiful. The roads wound through the forest, with tall trees lining both sides for much of the way.
Before reaching Crater Lake, we stopped at Rogue River Gorge, and all I can say is the pictures do not do it justice! The landscape was rugged, lush and incredibly green, with the Rogue River rushing through the narrow gorge, tumbling over large rocks and around fallen trees that almost looked like art. We followed a couple of the paths down for a closer look, stopping at different viewpoints along the way.
Crater Lake may have been our main destination that day, but Rogue River Gorge was a reminder of why it's worth leaving room for the places you discover along the way.
Seeing Crater Lake for the First Time
And then we arrived at Crater Lake National Park.
I had seen photographs of Crater Lake and knew it looked beautiful. But photographs don't really prepare you for that first view.
I had never seen a lake so blue—or so still. The deep blue water, with the surrounding trees reflected across its surface, was breathtaking.
I also hadn't known much about the history of the lake before our visit. Crater Lake formed in the caldera left behind after the collapse of Mount Mazama following a massive volcanic eruption thousands of years ago. Today, at approximately 1,943 feet deep, it is the deepest lake in the United States.
The lake is also home to two distinctive islands—Wizard Island, a volcanic cinder cone, and Phantom Ship, a much smaller rock formation that resembles a sailing ship from certain viewpoints.
One of the things I found interesting was learning that visitors have traditionally been able to hike the Cleetwood Cove Trail down to the lakeshore and take boat tours on Crater Lake. That isn't currently possible. The National Park Service is completing a major rehabilitation of the trail and marina, and the Cleetwood Cove Trail will remain closed throughout the 2026, 2027 and 2028 seasons. Public boat tours will also be unavailable during those three summers.
But don't let that stop you from visiting.
There is still so much to experience throughout the park, including taking in the lake from its overlooks and exploring the surrounding landscape. For us, one of the best parts was standing along the rim, looking out over that incredibly still blue water and trying to take in the sheer size and beauty of the lake.
We finished our visit with lunch at Crater Lake Lodge, the beautiful rustic lodge overlooking the lake. Sitting down to a wonderful meal with Crater Lake just outside the windows was a pretty perfect way to end our time there.
I had expected Crater Lake to be beautiful. What I hadn't expected was how much I would enjoy everything surrounding it—the drive, the forests, Rogue River Gorge. This area should definately be on your list to visit.
An Evening in Ashland
After a week filled with wine country, mountains, the Oregon Coast and so many unexpected experiences along the way, we spent our final evening in Ashland—and it turned out to be the perfect ending to our trip.
We started with dinner at Hearsay Restaurant, Lounge & Garden, where the food was incredible and I highly recommend if you are in the area.
From there, we headed to the Oregon Shakespeare Festival to see Come From Away.
Despite its name, the Oregon Shakespeare Festival isn't limited to Shakespeare. Its season includes a variety of productions, and Come From Away was being performed during our visit.
The musical tells the true story of what happened in Gander, Newfoundland, after U.S. airspace closed following the September 11 attacks. Thousands of passengers aboard diverted flights suddenly found themselves in a small Canadian community, where local residents opened their homes and their lives to complete strangers for several days.
Given the events behind the story, I expected parts of the performance to feel heavy—and they did. But what stayed with me most was its message about kindness, humanity and the way people can come together during times of crisis.
The cast was incredible, and the performance was moving, funny at times and ultimately uplifting. I walked away thinking less about the tragedy at the center of the story and more about the extraordinary way people responded to it.
After everything we had experienced during our week in Southern Oregon, there was something especially meaningful about ending our trip with a story centered around people opening their doors to others.
Southern Oregon: More Than I Expected
When I first started planning this trip, I knew Southern Oregon would be beautiful. What I didn't know was how much variety we would experience in just one week—or how many of my favorite memories would come from places and moments I hadn't expected.
I'll remember seeing the deep blue water of Crater Lake for the first time and standing beneath the towering Redwoods. But I'll also remember listening to music as the sun went down over a vineyard, learning about winemaking from someone who genuinely loved sharing what he did, watching longtime employees carefully pack pears during harvest, walking along the Pacific, meeting people along the way and even spending an evening working on a puzzle with a glass of wine and the ocean just outside.
That's what I loved most about Southern Oregon. There were certainly incredible places to see, but some of the best parts of the trip happened between the places we had planned to visit.
If Southern Oregon isn't already on your travel list, I hope this gives you a reason to consider it—and perhaps a few ideas for creating your own trip.
More Southern Oregon Guides Coming Soon
There is so much more from this trip that I couldn't fit into one article. I'll be sharing more about the Southern Oregon wineries we visited, along with additional tips and recommendations from our time in the region.
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