Okay, so Ashland, Oregon, right? Heard it was cute, wanted a little getaway. Here’s the lowdown on how it went down.

First off, booking. Found a sweet little Airbnb – a cottage kinda vibe. Scored it for a decent price ’cause it was mid-week. Definitely recommend checking Airbnb, some cool spots there.
Day 1: Hitting the Shakespeare Scene
- Landed in Medford (closest airport), grabbed a rental car – gotta have wheels, man.
- Drove to Ashland, checked into the Airbnb, dropped my bags. Quick change, then straight to the Oregon Shakespeare Festival.
- Caught a matinee – “Twelfth Night,” pretty good, even if I’m not a huge Shakespeare buff. The actors were into it, that’s for sure.
- Dinner: Found this pizza place downtown, Brickroom. Pretty damn good pizza and a decent beer selection. Casual, perfect after a show.
Day 2: Nature and Brews
- Morning hike: Lithia Park. It’s HUGE. Walked around, checked out the Japanese garden – super peaceful. Got some good pics.
- Afternoon: Beer time! Went to Caldera Brewing Company. Sampled a few, got a growler of my fave to take back to the Airbnb.
- Evening: Dinner at Standing Stone Brewing Company. Good food, good beer, nice atmosphere. Plus, it’s right downtown, easy to get to.
Day 3: Wineries and Waterfalls
- Wine tasting! Southern Oregon has some surprisingly good wineries. Drove out to a couple – RoxyAnn Winery was a highlight. Great views and the wine was solid.
- Drove out to see Mill Creek Falls and Barr Creek Falls. It’s a bit of a drive but worth it. The falls were beautiful, and the hike wasn’t too strenuous.
- Last dinner: Larks Home Kitchen Cuisine. A bit fancier, but the food was amazing. Splurged a little, treated myself.
Day 4: Goodbye, Ashland

- Lazy morning, packed up.
- Grabbed coffee and a pastry at Mix Bakeshop. So good.
- Drove back to Medford, dropped off the rental car, flew home.
Overall: Ashland’s a cool little town. The Shakespeare Festival is obviously a big draw, but the nature and the food scene are worth checking out too. Definitely a good spot for a relaxing getaway.
Things I’d do differently: Maybe spend an extra day. There were a couple of other hikes I wanted to do, and I could’ve hit up a few more wineries. But hey, gives me a reason to go back, right?