Doesn’t get much better than tiny house living!

I’ve really enjoyed getting to know the Southern part of Oregon this year. I’ve had so much fun exploring “Oregon’s secret wine country”, hiking waterfalls, visiting beautiful Crater Lake and enjoying new rivers and lakes. This Thanksgiving we did something a little unconventional and packed up in our Jeep Wrangler to drive to Roseburg and spend two nights tucked into the Oak filled forest hills.

The most peaceful vibe, Thanksgiving lost in the woods of Southern Oregon.

This was a family trip that was arranged by Travel Southern Oregon as an opportunity to share more about Douglas County with visitors and locals alike. It comes on the heels of another media trip to an area close by, also in Southern Oregon, but unique and beautiful all on its own.

Growing up my best friend would spend every Holiday in Roseburg visiting her grandparents, I had no idea how magical this sweet burg really is. We took our time meandering from Sunriver to Roseburg, traveling over a foggy Willamette Pass to Eugene and then South to the “Timber Capital of The Nation”.

Highway 58- Willamette Pass in late November.

As dusk settles in we arrived at 5k Ranch, an 160 acre farm that features an adorable and cozy Tiny House as well as two small cabins for nightly rentals. Our host and I share a first name- Renee’- and had checked in the prior evening to provide directions and recommendations for not only our stay but great places to stop along the way. She suggested Highway 138 “The Highway of Waterfalls!

The Highway of Waterfalls: Rogue Umpqua Scenic Byway or 138

Also known as the Rogue-Umpqua Scenic Byway. This 172-mile route winds through the Umpqua National Forest, connecting Roseburg to Crater Lake National Park. Along the way, travelers encounter over a dozen stunning waterfalls, including Toketee Falls, Watson Falls, and Clearwater Falls, each surrounded by lush forests and dramatic basalt cliffs. The highway offers ample opportunities for hiking, picnicking, and photography, with many waterfalls accessible via short, well-maintained trails. This breathtaking drive showcases the Pacific Northwest's natural beauty and is a must-see for nature enthusiasts.

Watson Falls on a “Green Friday” in 2022. Black Friday in Oregon means State Parks have free entry.

Checking into the Tiny House was super easy- just a ride up a gravel driveway and the whole 160 acre wood to ourselves!

I’ve found each Tiny House has its own individual layout and vibe. Maybe I’ve just revealed myself to be a Tiny House connoisseur, the truth is I lived in one for a while and fell in love with the charm and ease of ‘tiny life’.

The perfect Oregon hideaway, a relaxing evening settling into the tiny house in the woods.

I was excited to see that this particular tiny had a double loft and sitting area perfect for each of us (My husband, myself, and our 15 year old) to each have a spot to sleep and store our things. We used the sitting area to hang out, eat snacks, play games, and read. The kitchen area was ample and well appointed. The bathroom featured a composting toilet- if you have not used one before they can take a little getting used to. Everyone must sit to pee and solids require a scoop of sawdust to “flush”. Other than that- it’s life as usual.

The setting was so beautiful! Silence, stars, and cute lighting to boot!

Ambiance here was A-1! You can’t really beat the relaxation and restoration of a few nights in the woods, shut down from the hustle and bustle of everyday life. The stars were absolutely phenomenal and even though it was late November the trees were full of life- with fall colors and evergreens.

The next morning we packed up and hit the road to track down one of Oregon’s treasures- Covered Bridges! I love these types of adventures- connecting to the ways things used to be and learning more about our state.

We spent Thanksgiving morning exploring covered bridges of Douglas County.

“Covered Bridge of Douglas County” sounds like a movie, right? Douglas County boasts six charming covered bridges, each accessible via scenic routes.

Neal Lane Covered Bridge: the shortest covered bridge in Oregon in fall colors.

Neal Lane Covered Bridge: Built in 1929 and renovated in 2015, this is Oregon's shortest covered bridge (43 feet) and the only one using a kingpost truss. Directions: From I-5, take exit 108 to Myrtle Creek, then south on Old Hwy 99. Turn left onto Riverside Drive and right on Days Creek Cutoff Road. The bridge is on the left.

Horse Creek Covered Bridge: Originally built in 1930 over Horse Creek and relocated to Myrtle Creek’s Millsite Park in 1990, this pedestrian bridge spans 110 feet. Directions: From I-5, exit 108 to Myrtle Creek. Continue on Old Hwy 99 for a mile. The bridge is west in Millsite Park.

Cavitt Creek Bridge: Built for log trucks with Tudor-style arches, it spans Little River and was listed on the National Register in 1979. Directions: From Roseburg, take Hwy 138 east to Glide, turn right on Little River Road, drive 7 miles, and turn right on Cavitt Creek Road.

Milo Academy Covered Bridge: Oregon’s only steel bridge housed in wood, located at the Seventh Day Adventist Academy near Milo. Directions: From I-5, exit 98, follow Canyonville-Riddle Road, Main Street, and 3rd Street, then turn onto Milo Drive.

Pass Creek Bridge: Likely built in the 1870s, this bridge was relocated in 1987 for preservation. Directions: From I-5, exit 150, turn right on W A Avenue, and follow the signs to the bridge.

Rochester Covered Bridge: Built in 1933, it’s known for its curved-top windows. Locals saved it from demolition in the 1950s. Directions: From I-5, exit 136 to Sutherlin, turn right on Stearns Lane, then left onto Rochester Bridge Road.

You could spend several days exploring all 6 covered bridges of Douglas County.

This day we visited The Neal Lane Bridge as well as the Horse Creek Covered Bridge.

Next it was time to head to Melrose Vineyard Winery for their fabulous Thanksgiving Dinner buffet.

Melrose Vineyard Thanksgiving day buffet-intimate setting with a gorgeous view, food was good too!

Established in 1996 on the fertile bench land along the South Umpqua River, the vineyard spans over 250 acres and grows a variety of grapes, including Pinot Noir, Baco Noir, and Viognier. Known for its charming tasting room and picturesque setting, Melrose offers a warm and inviting atmosphere for visitors to sample its award-winning wines.

The grounds here are so pretty, a popular wedding venue.

The grounds here are known for hosting fabulous events and it's no surprise why- it was so pretty I could hardly stand it- especially as dinner was served up just as the pink glow of sunset erupted across the countryside. Our dinner was slow and relaxed and excellently prepared. It did feel a little funny to not cook or CLEAN….but sometimes new traditions are worth it.

A peak of Umpqua Valley Festival of Lights from across the river! What a sight.

Our drive back to the Tiny House was just a few short miles but we did pass by The Umpqua Valley Festival of Lights- it was visible across the river and was such a surprise to see on our drive. This family-friendly event transforms River Forks Park into a dazzling winter wonderland with over 90 light displays, including the iconic 90-foot-tall "World's Largest Nutcracker."

That night we passed the time playing games and connecting, just the three of us. Life is short and I’m thankful for the quality time and peace we have together as a family, it means so much.

Waking up in the loft is so fun! I wore my Pendleton Glacier driftwood shacket for good luck….

We had brunch at Brix Grill in downtown Roseburg.

Our last morning in Roseburg was quiet and sweet, filled with pour over coffee, guitar melodies on the front porch swing and a drive downtown for lunch at a very hip spot called Brix Grill. Offering a blend of American comfort food and innovative dishes, Brix serves breakfast, lunch, and dinner, with standout options like gourmet burgers, fresh seafood, and creative pasta dishes. The restaurant also features a well-stocked bar with craft cocktails, local wines, and beers. It was very festive and very good.

The Bistro BEST: bacon, egg, spinach, tomato! So good.

Right next door is the best spot I could think of to spend “Black Friday”- Farmhouse Decor: a boutique store specializing in rustic, charming, and country-inspired home furnishings and décor. The shop offers a carefully curated selection of vintage furniture, handcrafted pieces, repurposed items, and unique accessories that embody the cozy and timeless farmhouse aesthetic. From distressed wood tables and antique-inspired wall art to soft textiles and seasonal decorations.

Vintage shopping on Black Friday in downtown Roseburg.

Such amazing treasures in Farmhouse Decor

I love thrifting and antiquing in Oregon. Always on the hunt for a little piece of history.

I was so excited to find a mid century Pendleton Glacier Park blanket! Wow, what a true Oregon find. I actually found a few items I will be wrapping up as gifts this Christmas season. I really appreciated the collection of vintage items and seasonal displays.

Look what I found! a Mid Century Pendleton Glacier Park blanket! Wearing my matching shacket really did bring me luck.

I did lose Dave to the music store across the way, which was still settling into their new space downtown. The proprietor however is no stranger as he has lived in the area for over 60 years. We had a nice chat about how this part of Roseburg was once the heart of it all- with Christmas songs playing out of a loud PA system for all to hear. He shared with me some bits about Winston (a “one stoplight” town that is worth the visit) and you could tell his heart was for Roseburg- a tiny town with so much to explore.

Someone said to me that this part of our state is really coming into its own time- with so many delicious foods and wines produced here, the landscapes, history, and fun events stacked up. I have to agree, this is my 5th time in Southern Oregon this year alone and I have enjoyed every single visit.

Travel Southern Oregon: Roseburg

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