D A Y T R I P: Ashland, Oregon

Located 2 hours north on the 5, Ashland, Oregon is a rad little town. With a creek that runs through the heart of the historic downtown corridor, it couples a quaint, cozy vibe with a bit of a boho and hippie flair. Whether it’s shopping, food, or great coffee you’re looking for, it’s the perfect day trip to escape NorCal for a bit of an adventure.

Keep reading for our favorite stops after the jump!

We began our day by placing our car in the park. With long paved trails, live music on the weekends, and pathways to the artisan circle. Start your day here. On the weekends, follow the creek up to the street and look at the artisan fair. From woodworking to flower crowns and fine art, discover the boho vibe that this town offers. Continue up the sidewalk to various boutiques, shops, and restaurants.

Here are some of my favorites.

Small Change Children’s Store: Featuring ethically minded clothing, head here for some unique pieces for your favorite little.

The Spice and Tea Exchange of Ashland: Located in the Downtown core, this is a favorite stop. Purchase spices and teas by the ounce at an affordable price. My essentials, peach tea and dried lavender for summer and truffle salt for one of my favorite egg dishes.

Papaya Living: Featuring fair trade textiles, women’s fashion and beautiful gemstone jewelry, this is a great spot for a unique item. Head downstairs for items from Free People, Everlane, and Desigual.



After a 3 hour walk around town, we decided to was time to relax at Weisinger Family Winery. Featuring affordable tastings at $5 a flight, this winery overlooks the mountainside. With live music on the patio on the weekends and a three-tier shaded deck it offers a welcome, chill approach to the wine scene.

Case coffee. Make sure to head here for an afternoon pick me up. Featuring coffee that’s locally roasted with classic Pacific Northwest notes of chicory, they feature a simple menu with delicious brunch items. We had two iced lattes to cool off and purchased a few bags of coffee to enjoy at home.

Brickroom: With creekside dining and a rad interior, this restaurant serves variations on pub food that are killer. We opted to do a few small plates after snacking at the winery. We ordered chicken tenders and sambusek. Both were surprising in their preparation and perfectly on point.

Oregon Shakespeare Festival: While we didn’t catch a show this time, for any thespian this is a must-see, and nationally known spot for good reason. Make sure to stop by the box office in Downtown and see what is playing.

Until next time Ashland!

Leave a Comment

Your email address will not be published. Required fields are marked *