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

The Peerless Restaurant - Ashland, Oregon - USA Travel

Ashland, Oregon is stunning at anytime of the year. 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 in love with this cultural capital again. 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 fall is simply a magical time to visit a place like Ashland. The hot weather has dissipated for the most part, but it’s still perfect and 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 to Ashland, Oregon.

Watching Great Expectations at OSF

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

I wrote up my experience at the Oregon Shakespeare Festival last year on this blog and how impressed I was with it then. 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 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 wasn’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 did enjoy 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

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!

Touring Branson’s Chocolates

Branson's Chocolates in Ashland, Oregon - USA Travel

As much as I love chocolate, I’ve never actually toured a chocolate shop or factory before. This all changed when I walked into Branson’s Chocolates in Ashland 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 that she infuses with local craft beer. Um yes, please!

Relaxing Under the Trees at Caldera Brewing

Caldera Tap Room - Ashland, Oregon

Okay, I couldn’t visit Ashland 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 downtown 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.

Dinner at The Peerless

The Peerless Restaurant - Ashland, Oregon - USA Travel

A favorite dinner of mine in southern Oregon was at the historic Peerless restaurant. 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 is the place to go for fine dining in Ashland. They have a lovely outdoor area with lounge chairs and twinkling lights. It’s the perfect place to take a glass of wine and sit outside in 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.

Have you been to Ashland before or experienced any of these local activities? What is your favorite area of Oregon?

If you’d like to check out my top 7 things to do in Ashland from last year, you can find the post here.

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

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

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Mimi McFadden
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Mimi McFadden

Travel Writer/Blogger at The Atlas Heart
Mimi founded The Atlas Heart to create a community of travelers inspired to see the world. The Atlas Heart is a space where you'll find anecdotes on slow travel, craft beer, outdoor adventures, and all the eccentric bits in between that this world has to offer.
Mimi McFadden
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