It’s a fairly bold statement, “Why Everyone Should Visit Ashland, Oregon” but sometimes you just gotta make a big statement.  And, as long as you can back it up, why not go bold?

  • If William Shakespeare, Bob Marley and Daniel Boone were planning a vacation together, they’d probably be able to agree on Ashland, Oregon.  Arizona Central

In 2011 we said farewell to our California lives and looked to the north, to Ashland.  If I told you we knew everything there was to know about Ashland before deciding to make it our home, I’d be lying.  We knew bits and pieces, but nothing substantial except for a handful of absolutely critical tidbits that would prove to be determining factors for our relocation destination.  The Oregon Shakespeare Festival was the #1 big ticket item.   If you’re going to own/operate a B&B, you better have a guaranteed (and repeating) guest book.  The festival would almost guarantee a successful  customer base as it is the leading draw to the City of Ashland.

The Oregon Shakespeare Festival

Founded in 1935, it can be said the Oregon Shakespeare Festival is the cornerstone of Ashland.  The festival, which is actually not a festival by definition, as it lasts 9 months, draws approximately 300,000 visitors to Ashland each year.  Let that sink in.  Three hundred thousand visitors each year to a city which is home to a population of only 21,000.  During the summer months, the city boundaries swell like a balloon full of air.  What more could we have asked for as a location for a B&B?

Image result for pictures of the oregon shakespeare festival

The Bowmer Theater makes for a glorious “under the stars” evening of theater.  Photo credit:

Each season the festival presents eleven productions, approximately five classic works of Shakespeare and the rest are works by other playwrights.  All of which take place on three stages and of the three stages, the Bowmer Theater is an open air theater which makes for a glorious night of “under the stars” entertainment.

The Rogue River

The Oregon Shakespeare Festival is definitely a reason why everyone should visit Ashland, Oregon.  Theater pleases the imagination and leaves the audience basking in the story, the costumes, the music, and the engagement of live theater.

But, there is so much more. The outdoor year-round recreation that keeps people returning to the Rogue Valley year after year after year is another cornerstone of the Ashland foundation.  But, don’t just take my word for it.

  • “Ashland is the gateway to the Pacific Northwest. Home to four seasons of world-class outdoor adventures, the world-renowned Oregon Shakespeare Festival, a foodie’s paradise, a fast growing wine industry and a refreshingly modest non-snob underground beer scene. Ashland is a phenomenal vacation that caters to a plethora of tastes, styles, and ideas of what the perfect vacation might be.”  Will Volpert – Indigo Creek Outfitters.

Rafting the Rogue River is an absolute must do and there is no finer crew on the river than that of Indigo Creek Outfitters.  And, I’m not just saying that… I speak from experience.  We had the most fun we’ve ever had on a river when we climbed in to the raft and set off down (up?) the river with Will.


All kinds of fun on the Rogue River! That’s me on the right side in the back. I’m not particularly brave so if I can do it, for sure you can do it!

Pardon the Pun

We landed in Ashland at just about the same time Will launched (pardon the pun) his company and we developed a working relationship, which quickly turned in to a genuine friendship and I’m pleased to say we are still friends.  So, when I say you should paddle the river with Will, I can offer my personal assurance that you’ll enjoy a fantastic river experience.  If you want more than just an afternoon on the river, Will and his crew offer multi day camp/rafting experiences.

The Ashland B&B Experience

The B&B experience is actually synonymous with a vacation in Ashland.  If you look at TripAdvisor you might see 30+ B&B’s listed in the City of Ashland, but if you look for the true B&B properties, (no small motels, etc.) it’s actually less than that number.  And, all of the B&B’s offer lovely accommodations hosted by experienced innkeepers.


Chanticleer Inn Bed & Breakfast, Ashland, Oregon.  Photo credit:  Chanticleer Inn Bed & Breakfast Inn.

Of course I like to say we had the best B&B in town, but as you well know by now, we sold our inn just 3 1/2 years in to our lives as innkeepers.  Although we went in with a ten-year plan, the universe presented us with a life-changing opportunity and we took that leap of faith and never looked back.  When it’s right, it’s right.

B&B Stays

An average stay in Ashland is three to four nights and the B&B stay is the perfect fit for most visitors as the B&B’s in Ashland all offer similar accommodation experiences.  For example, guests at the Chanticleer Inn Bed & Breakfast start their days with a delicious and hearty breakfast, expertly prepared by their host (and our friend) Ellen – who by the way has authored two cookbooks – and then they head out for the day to explore the city and/or the surrounding Rogue Valley.  NOTE:  The Chanticleer is now under new ownership (2020).


A lovely way to start the day while enjoying the B&B experience. Most B&B’s serve a 2-course breakfast.  Photo credit:  Chanticleer Inn Bed & Breakfast.

What Could be Better?

Guests might take a long walk in Lithia Park, or a regional guided tour. Or, guests might explore the burgeoning wine region, or take a hike to the top of Table Rock Mountain.  Even better enjoy a day on the Rogue River.  With such a filling breakfast guests quite often skip lunch. They  might head back to their accommodation for late afternoon tea and cookies.  Then, it’s out to dinner and an evening theater performance.  What could be better?

The Rogue Valley

Although the average stay in Ashland is three to four nights, don’t let that stop you from booking a longer stay.  The entire Rogue Valley and surrounding region offers visitors a host of day trips.

It wasn’t often that we could break away for the better part of an afternoon.  Especially, while we were in high tourist season at our B&B, but when we did one of our absolute favorite places to visit was Lake of the Woods.  I’m not exactly sure as to why we fell in love with the lake.  The stunning surrounding forest, and the old school wooden lodge offered a place of solace. The lake spoke to us and it became our go-to respite.


Lake of the Woods – just about 45 minutes from Ashland.

Once we arrived at the lake we would sit out on the deck and order cheeseburgers and fries.  Long after finishing our lunch we’d still be on the deck. Sitting in brightly painted red Adirondack chairs with our eyes cast upon the sun shimmering across the lake water.  Or, with our eyes closed and perhaps snoozing just a bit. Either way, it was a little slice of paradise.

Destination Day Trips

Located just 15 miles north of the CA/OR border, the Rogue Valley offers some of the finest recreational opportunities in the Pacific Northwest.  Visitors to Ashland can head in just about any direction and within an hour or two, they can have their choice of destination day trips.  Here are some of our favorites.  Each destination is linked to our post about our time spent at these incredible places.

Lake of the Woods

Umpqua Scenic Byway

$8 Mountain & The Illinois River

Burney Falls State Park

Crater Lake

Mountain Lakes

Upper Table Rock Mountain

Why Everyone Should Visit Ashland, Oregon

The local culture in Ashland embraces life wholeheartedly.  It’s pretty hard not to when – as a city – you’re home to a world renowned Shakespeare Festival and Southern Oregon University, and by far the best Halloween parade you could ever hope to watch pass by.  Culture and imagination flourish in Ashland.  And, I haven’t even told you about the amazing food scene.

If you’ve been fortunate enough to spend time in the Pacific Northwest or more specifically in the Rogue Valley, you well-understand the thought that Daniel Boone, Bob Marley and William Shakespeare would all agree upon Ashland as a vacation destination.   The only questions left unanswered is about you… have I convinced you that everyone should visit Ashland?


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