Road Trip: Ashland

In Ashland, it’s always a wonderful time for a bit of indulgence: world-class theater, culinary delights, restorative spa escapes or time with family. The Oregon Shakespeare Festival (OSF) runs from February through October, featuring four stages of classic Shakespearean plays, quirky musicals and innovative modern tales. All the excitement will leave you hungry for Ashland’s… More
: Photo credit: Sean Bagshaw


It’s easy to fall in love with Ashland. We don’t blame you for extending your stay.

Home to the world-famous Oregon Shakespeare Festival and ranked in the top 10 of “The 100 Best Small Art Towns in America,” Ashland is a cultural hot spot, with award-winning galleries, theaters and restaurants bursting from its seams. Nestled at the base of the Siskiyou and Cascade mountain ranges, Ashland has a reputation for great outdoor recreation in the city limits and beyond. And with the famous Mt. Ashland Ski Area nearby, fun stays in Ashland year-round.

Trip Ideas

Arts & culture around Ashland

Wine, Music and Theater in Southern Oregon
Jacksonville, Southern Oregon
Southern Oregon Arts & Bounty Electric Byway
Southern Oregon Lavender Trail
Oregon Dreamer Bill Rauch
Wine Tasting, Artisan Meals and Shakespeare
Oregon Shakespeare Festival’s Freda Casillas

Outdoor adventure around Ashland

Run Away to Southern Oregon
Appetite for Adventure in Southern Oregon
Winter Angling in Southern Oregon
Hike and Raft in Southern Oregon
Off-Season Ski Area Adventures
3 Must-Hike Trails in Ashland
Oregon’s King of the Trail: Hal Koerner
The Oregon Cyclists: Satin Sheets in Ashland

Tasty detours around Ashland

Tasty Salmon Tips for the Season
Celebrate Thanksgiving in Oregon Wine Country
McMinnville, Willamette Valley
Southern Oregon Dining Guide
Decadent December
Pedal and Sip in the Applegate Valley
Grants Pass, Southern Oregon
Tasty Road Trip: Southern Oregon
Coffee Lover’s Guide to Oregon
Portland, Oregon Coast
Southern Oregon Taster’s Tour
Jacksonville, Southern Oregon

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Ask Oregon

What Ashland activities do you recommend?

Ashland is our hometown, and we love it! I’m sure you’ll enjoy a visit. Without knowing your interests, I can tell you that we believe the Oregon Shakespeare Festival to be a must-do; this season of high quality plays and performances run nearly year-round and peak in the spring through summer. I recommend seeing at…

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