Ashland, Oregon in the Fall – Why You Need to Go!

The Peerless Restaurant - Ashland, Oregon - USA Travel

The Best Time to Visit Ashland, Oregon? The fall. This is why.

Although the city is stunning at anytime of the year, I personally think the best time to visit Ashland, Oregon is in the fall.

I visited the city for the first time last summer when I went to my first Oregon Shakespeare Festival production. This year, I had a chance to visit again in the early fall and I fell even more in love with Oregon’s cultural capital.

One aspect that Oregon does well is fall foliage and although Ashland is almost to the California border, it still has beautiful mild seasons and colorful leaves in the fall.

This time I didn’t have full days of trying to fit in as much as possible like I did last summer, but a more relaxed and local experience that sat well with me.

I still managed to get to another Oregon Shakespeare Festival play to my excitement and I squeezed in a pint at Caldera Brewing, but, other than that, I had a lot of new experiences that further endeared me to the city.

Although you can do most of these activities year round, I think doing them during the Ashland, Oregon fall is simply a magical experience.

The hot weather has dissipated for the most part, but it’s still sunny every day. The hoards of tourists have disappeared, and there’s a quiet elegance that allows you to just enjoy your surroundings in the best way possible.

These were some of my favorite activities I took part in with a recent visit, and why I think everyone should visit Ashland, Oregon in the autumn at least once.

Note: this post contains affiliate links, which help run this site at no extra cost to you so I can keep providing free travel advice and tips. 

Related: Top 7 things to do in Ashland, Oregon

Watching Great Expectations at OSF

Great Expectations at the Oregon Shakespeare Festival - USA Travel | Ashland Oregon Fall
Pip (Benjamin Bonenfant) and Miss Havisham (Judith-Marie Bergan). Photo by Jenny Graham

I already wrote up my experience at the Oregon Shakespeare Festival last year and how impressed I was with it. It’s easily one of my favorite Ashland, Oregon activities to do when I’m in town.

OSF is something I had wanted to experience since I was a little girl growing up in Santa Cruz and I went to my first Shakespeare Santa Cruz Production. When I had the chance to visit Ashland, Oregon again this fall, I jumped at the chance to see another OSF play before the season finished at the end of October.

And it just so turned out that they were doing a production of Great Expectations, one of my favorite books from my many English literature classes growing up.

Although it isn’t Shakespeare, Dickens is a good runner up. This year was the first time that the book had been adapted to a play in this manner, so it was a world premiere adaptation.

Great Expectations is not the easiest book to make into a theatrical production, but OSF somehow did it in a captivating and unique way. I enjoyed the energy of the two musicals I saw last year a bit more, but I think that’s just because I’m a musical type of gal.

This upcoming summer/fall season they’ll be doing a production of Beauty & the Beast and Shakespeare in Love, which both sound amazing. Too bad I won’t be stateside for awhile, but if any of you happen to be in Ashland at that time, send me reviews!

Wine Tasting at Grizzly Peak

Grizzly Peak Winery in Ashland, Oregon - USA Travel | Ashland Oregon tourism

My wine tasting experience in southern Oregon was top notch. I drank more than my fair share of wine over the course of 3 days and had a lot of tasty local cuisine. One of my favorite wineries that I visited was Grizzly Peak, just a few minutes from downtown Ashland.

Grizzly Peak Winery was started in 2006 by a couple who came up from Berkeley, California. Walking around the property, you couldn’t help but feel inspired and relaxed. Everything was new, clean, and beautiful.

They have a large indoor events area that’s in the shape of a barrel for the many live acts and private events they host. The winery itself was one of the most picturesque wineries I visited during my time in southern Oregon.

It helped that I ate lunch out in the midst of the vineyards on a sunny day. It’s hard to beat that!

Related: The Complete Guide to Wine Tasting in Southern Oregon

Touring Branson’s Chocolates

Branson's Chocolates in Ashland, Oregon - USA Travel | visit Ashland Oregon

As much as I love chocolate, I’d never actually toured a chocolate shop or factory before. This all changed when I walked into Branson’s Chocolates near downtown Ashland, Oregon and met with the owner, Deena Branson.

You can tell Deena’s passion for chocolate as soon as she starts talking about her company. She has been a part of the chocolate business for over two decades now, first starting out as a manager for another popular chocolate store and then opening up her own store when that one closed down in 2005.

As she walked us through the process of making her chocolates – everything from the molds and equipment to the packaging – you couldn’t help but be captivated by her dedication to the craft.

Everything is made by hand in her shop and the flavors from her products are proof of that. She also offers vegan and sugar-free chocolate, so all diets can enjoy her craft.

This is definitely a place to stop in for a chat with Deena and to taste some of her unique creations. My personal favorite? The truffles infused with local craft beer. Um yes, please!

Related: A Pioneer Gold Rush Town in Oregon: Jacksonville

Relaxing Under the Trees at Caldera Brewing

Caldera Tap Room - Ashland, Oregon | best time to visit Ashland Oregon

Okay, I couldn’t visit Ashland, Oregon and not go to at least one craft beer spot.

I made it to almost every brewery in town last time I was in Ashland, and I decided to go back for a chilled out afternoon at Caldera Brewing during this visit. 

Their tap room in downtown Ashland is one of the more relaxing places to sip on an ale. It’s shaded under colorful leaves in the fall and their patio somehow always seems to be the perfect temperature.

The Caldera tap room is one of those places where you could spend all day at and never want to leave. I’m glad I was able to go back for another visit to sit back and appreciate my time in Ashland on the slow side.

Related: 14 Stops to Make on an Oregon Coast Road Trip

Dinner at The Peerless

The Peerless Restaurant - Ashland, Oregon - USA Travel | Peerless Ashland

A favorite dinner of mine in southern Oregon was at the historic Peerless restaurant (one of the best restaurants in Ashland, Oregon).

It was my last dinner in the region and I was surrounded by friendly people, wine enthusiasts, and tourism board representatives. We must’ve had about 25 people at our table, yet the whole evening was relaxing and fun.

The Peerless Ashland is the place to go for fine dining in the city. They have a lovely outdoor area with lounge chairs and twinkling lights.

It’s the ideal place to take a glass of wine and sit outside to enjoy the warm fall evenings. The executive chef David Taub knows what he’s doing in the kitchen and came out with unique and flavorful dishes all night long.

The Peerless restaurant is actually a new addition to the original Peerless Hotel, that sits right next door. The Peerless Hotel is run by the same owner as the restaurant, Crissy Barnett, and is a relic from the old railroad days in southern Oregon.

Built in 1900, the hotel used to be a boarding house for Southern Pacific railroad workers and the accommodation has been restored to resemble its former glory.

It is a beautiful property that is worth taking a tour of or at least walking into, even if you’re not staying there. And Crissy is simply a lovely and knowledgeable woman to have a chat with about the history.

Related: 6 Unique Things to do in Grants Pass, Oregon

Recommended Ashland Oregon Accommodations

Whether it’s an Ashland bed and breakfast or one of the cozy boutique Ashland hotels, there are plenty of options for accommodation in Ashland, no matter your budget.


Flagship Inn of Ashland

One of the most popular budget hotels in Ashland, Oregon, Flagship Inn offers air conditioned rooms featuring floral decor and work desks. There is also a swimming pool and La Casa Del Pueblo restaurant on-site, serving up Mexican cuisine and cocktails. Only a 5 minute walk from Southern Oregon University.

Check availability & pricing here


Ashland Hills Hotels & Suites

I stayed at the Ashland Hills Hotels & Suites while I was in Ashland and was very happy with my stay. The hotel is situated a little ways outside of downtown, so best to stay at only if you have a car. Think 70’s inspired decor that is clean and modern. Also features a refreshing outdoor swimming pool, decent breakfast, and panoramic mountain views.

You can read my full review of this accommodation here.

Check availability & pricing here


Bard’s Inn

One of the most popular Ashland hotels to stay at for those who are in town for the Oregon Shakespeare Festival. Bard’s Inn is only a 6 minute walk from the Shakespeare festival, right in downtown, and offers both a pool and hot tub to soak in after shows. There is also a quality free breakfast included every morning.

Check availability & pricing here


Winchester Inn

Part hotel, part bed & breakfast, the Winchester Inn is one of the better luxury stays you can have in Ashland. Besides the comfy and spacious rooms with down feather beds that include 600 thread count sheets, there is an on-site bar and restaurant with an open patio, free parking, coffee bar, and a free 2-course gourmet breakfast in the mornings.

Check availability & pricing here

Have you made a visit to Ashland, Oregon before or experienced any of these local activities? What is your favorite area of Oregon?

Note: I was a guest of Travel Southern Oregon & the Ashland Oregon Chamber of Commerce, but all opinions, as always, are my own. 


Looking for more Oregon travel inspiration? Check out these related posts!

The Best Things to do in Florence, Oregon

Jet Boating the Rugged Rogue River

8 Things to do in Bend, Oregon in the Summer

The Perfect Day Trip from Portland


Ashland, Oregon in the Fall - Why You Need to Go!

Pin this image for future reference by clicking on the top right hand corner

Mimi McFadden
Find Me