As a young woman, pre-kids, I remember a mentor telling me about the quaint Ashland Oregon.  She raved on about outdoor theaters, the Oregon Shakespeare Festival, the cute boutiques, and the lovely cafes lining Ashland Creek.  I dreamed of a romantic weekend getaway enjoying the town with my husband.  However, that sadly never happened.  But during our road trip in Southern Oregon, I found ourselves just a short drive from Ashland during the COVID pandemic.  Would the town live up to my image set so long ago?  And was it worth the visit during COVID and with two kids in tow? The answer is a resounding yes!  And I cannot wait to return when the theaters open.  Check out what to see and do, and how to stay safe when visiting Ashland Oregon. 

Breakfast

We visited Ashland the day we were planning to return to California, so we packed up from our hotel in Medford early, and headed to Ashland so we could have breakfast and then walk in town.  There were so many good options, it was hard to choose from.  But ultimately, we ended up at Brother’s Restaurant, thanks to its classic breakfast menu, good reviews, and having a table for four available outside.  I love a big breakfast with eggs, hash browns and a good mimosa, and Brother’s had all of that and more.  My son and I got big omelettes chock full of veggies and cheese, big servings of crispy hash browns, and a scone on the side to boot.  My husband ordered a spicy scramble with chorizo, while my daughter ordered the French toast platter.  You know the food is good when my daughter finished the clean plate club, that never happens! 

Walking in Town

After such a big meal, we needed to walk some of that off, so we started walking into town to check out the famous boutiques and theaters that I had heard about all those years ago.  Due to COVID, none of the theaters were open and there were no shows, so we did not get to experience the famous theater scene Ashland is knowns for.  But we did walk down to the theater district, looked at the map, and were able to see the famous theaters from the outside. 

A nice surprise while walking around town was finding a sculpture dedicated to the artists of the Ashland.  It was in a square right on the main road, and was beautifully done with life like carvings, extensive detail, and lots of feeling and emotion.  We also were able to see some art and famous costumes in windows for view since some of the galleries themselves were close. 

There were also so many lovely boutiques with quirky finds along the road.  I enjoyed window shopping and looking at the scarves, home décor and fashion through the windows.  We found one large shop with three levels that looked relatively empty, so we walked inside to check it out.  There we found lots of cute gifts, books, quirky signs, lovely bags, and fashion.  We managed to walk out with just a few quirky masks.  The gummy bears one has become my husband’s favorite!

Along Ashland Creek

On our way back, we decided to walk along the creek.  We found Calle Guanajuato, a pedestrian only walkway behind several restaurants.  There are several tables outside that allow the diners to eat while overlooking Ashland Creek. 

From there you can access a bridge into Calle Guanajuato Park, which has a tree-shaded path along Ashland Creek.  There you can watch the rushing water on the creek, sit on a bench under a tree to think, or enjoy nature right in the middle of the city.  Near by is Lithia Park, a famous much larger park in Ashland with several trails, a lake, and a lovely playground. 

COVID Consideration

At the time of the visit, September 2020, Oregon was allowing indoor dining at a limited capacity. However, Ashland has blocked off parts of streets to allow restaurants and cafes to expand their outdoor dining. Masks are required in all public spaces, and at tables when you are not actively eating. All the shops have hand sanitizer available for use, and are limiting the number of people allowed inside. Unfortunately, the famous theater scene is not open at time of publication.

After a couple of hours of walking, it was time to jump in the car and start the five-hour drive back home.  We dawdled on our way back to the car, soaking every minute of the picturesque town, the beautiful trees, and the memories that Southern Oregon offered us. 

Note:  The day after we left Ashland, the Almeda Fire broke out and wiped out parts of Ashland, Phoenix and South Medford.  While the downtown was spared, many people lost their homes.  This is a town that’s main industry is tourism, and its economy has already been badly hit due to the pandemic.  The people who lost their homes are truly suffering.  If you wish to help the people of Southern Oregon, please check out this page for what non-profits are helping and where to best send your donation. 

* Starred Photos taken by Atma Photography

*Disclosure: This post may contain affiliate links that allows me to earn a small commission at no cost to you. I only link to products I would or have used myself and all opinions expressed here are my own. You can read the full disclaimer here.