Things to do in & around Ashland, Oregon

Maybe you’re heading to Ashland with an agenda in hand, or maybe you’re ready to discover your new favorite hiking trail and taphouse? Either way, we know you’ll find lots to delight in during your stay.

Whether you’re an Ashland-traveling veteran or visiting for the first time, we want to share some of our local favorites. Our family loves living and playing in this sweet community, and we hope you’ll pocket some great memories while you’re here, too.


Move over, Napa! Southern Oregon gives the great wine-tasting regions of the world a run for their money. You could spend DAYS tasting your way through the Rogue Valley, Applegate Valley and Illinios Valley — all within driving distance of our homes in Ashland.

If you’d like to stay local, our favorites in Ashland are Dana Campbell (for the expansive mountain views) and Irvine Roberts (for the Pinot noir and Chardonnay!). Weisinger’s is also a great stop on your way to or from Mt. Ashland.

Outside Ashland, head to Medford for RoxyAnn Winery and neighboring Dunbar Farms (a tiny seasonal tasting room with great views of Table Rocks). From there, you can head north toward Kriselle Cellars, or west past Jacksonville to explore the Applegate Valley (about 40 minutes from Ashland). There, you’ll find creekside sipping at Red Lily Vineyards, creamery pairings at Wooldridge Creek Winery, and a really great fireplace at Schmidt Family Vineyards. This is truly just a small sampling of some of the favorites!

If you’d like to hand the reigns to a designated driver for the day (or days), we recommend Wine Hopper Tours or Bravo Outings.


Ashland has so much to offer any time of year — it’s not an exaggeration. From ScienceWorks Hands-On Museum (for the family on indoor days) to hundreds of miles of downhill bike trails, you’ll find plenty to keep your time occupied in all the best ways.

There are also some festivals in Ashland that bring a little “extra” to the Ashland stage. The Oregon Shakespeare Festival is the best-known and serves up award-winning live shows seasonally.

We also love the Oregon Chocolate Festival in March with truly EVERYTHING chocolate (spa treatments, science experiments, body care products, wine pairings…you name it).

The 4th of July Parade is always a big hit downtown, as is the annual Children’s Halloween Parade on October 31st. One of our favorites is the Festival of Lights parade the day after Thanksgiving each year. Come watch Santa make his way downtown, sing-along with the entire crowd of thousands, and then count down to an all-at-once-light-up of the buildings and trees for the holidays. Follow up with cocoa from Mix Coffeeshop and you’ve got yourself an annual family tradition.


Visit those award-winning restaurants and destinations you’ve been reading about! Ashland and Southern Oregon are home to world-reknowned fare — from coffee and wine, to restaurants and producers. Some are just a short walk away from our downtown Ashland properties, while others are a short drive. In addition to too many award-winning wineries to count, here are some of our local favorites…



One of the Best 50 Restaurants in America, New York Times



Food & Wine Magazine’s Best Coffee in Oregon, 2018 & 2022



Numerous Good Food Awards



World’s Best Cheese at World Cheese Awards

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