Things to do in Ashland, Oregon

ashland oregon guide

Sam had an art show recently in Ashland, Oregon. It’s a quaint town about 6 hours south of Portland (and about 6 hours north of San Francisco), near the border of Oregon and California. I wasn’t able to make it to the show (bad wife alert!), but I did promise to help haul his pieces back to Portland after the show.

So this past weekend, we rented a mini van (did I mention his art is LARGE!?) and make the trek down to Ashland. It was a lovely little trip because we made a weekend getaway out of it.

I had never been to Ashland, but it wasn’t hard to find the area’s hidden gems. Here’s a look at some of the highlights of our trip in case you’re headed through Southern Oregon anytime soon.


Lithia Park

The Central Park of Ashland, Lithia Park backs up to the heart of the town. We took a brief stroll, but it’d be easy to spend a full day wondering through the different paths.

Farmers Market 

I’m a big sucker for local farmer’s markets. Naturally when we (accidentally) stumbled upon one in Ashland, I had to stop and check it out. It wasn’t huge, but it was worth a stop, if for nothing else but the farm tools photo snapped below. Oh, and some fresh pastries. For more information on hours and locations, visit the Rogue Valley Growers and Crafters Market.

Dragonfly Cafe and Gardens

Dragonfly Cafe is a fusion of latin and asian foods – which is pretty much the sweet spot for Sam and I when it comes to dining. They also had an amazing outside dining space (hence gardens in the name). We made a stop for brunch and were really pleased we did.

Cowboy Bistro

We were told that Cowboy Bistro was a must-stop in Ashland. We were also told not to be frightened off when we first arrived. I was glad for the warning. From kitschy fake flowers to cow wall paper, Cowboy Bistro is pretty… unique. But the food was killer, and we’d definitely go back. 

Mix Bakeshop

One of the first things I noticed about Ashland was the absence of big box stores. It was totally refreshing. I love venturing into independent stores and little coffee shops – and it didn’t take long for us to stumble upon Mix. The coffee shop serves Stumptown Coffee (one of our Portland faves!) and tons of freshly baked treats. Totally a win win.


Ashland is known for its strong theatre community including the annual Oregon Shakespeare Festival, which attracts people from around the world. The town is dedicated to its theatre roots, and we found theatrical symbols – from posters to costumes – nearly everywhere we went.

We scored discounted tickets for one of their current shows – Water By The Spoonful – and I’m so glad we went. It was seriously Broadway-quality. If you don’t have a specific show in mind, and you’re frugal like I am, I highly recommend getting to the box office early to request discounted ticket prices.

Harry & David

Two words: Moose Munch. Harry & David, known for its fruit and holiday baskets, is located in Medford – just north of Ashland. Tours are only offered M-F, but we still made a dash into the gift store to stock up on some of our favorite products, plus some snacks for the drive home.

Rogue Creamery

Rogue Creamery is another must-stop just outside of Ashland. I haven’t been to such a lovely creamery since we were honeymooning in France. This is the perfect place to pick up a bottle of wine and a few pieces of cheese for a picnic in Lithia Park!

ashland mix bakeshopashland lithia parkashland farmers marketcowboy bistro ashland oregonashland theatre

rogue creameryashland rogue creamery

Harry & David 

2 Responses to "Things to do in Ashland, Oregon"

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  1. Eeeeee cheese cheese cheese!

  2. Anonymous


    Aloha Marisa: Nice post on Ashland. I love that town.


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