Summer is just around the corner, so get your planning started now to make the most out of the sunnier seasons. Become the hero of your family and friends this year by planning a getaway to Ashland, home to award-winning local restaurants, unbeatable nature trails, the world-famous Oregon Shakespeare Festival, and so much more.

Nestled in the heart of Southern Oregon—just a five-hour scenic drive from Portland—Ashland is a destination site that draws travelers from near and far. Doubt that? Just ask USA Today, who voted Ashland one of the “Best Small Towns” in the United States in 2023. Keep reading to learn more about the picturesque arts town and all the adventures waiting for you, on and off the stage.

Experience the Oregon Shakespeare Festival’s outdoor season

There’s nothing quite like experiencing live theatre under those unbeatable Southern Oregon stars. OSF kicks off its outdoor season in the iconic, open-air Allen Elizabethan Theatre this month with Jane Eyre, followed by Much Ado About Nothing. These two shows join this year’s captivating OSF lineup that also includes Shakespeare’s epic tragedy Macbeth, the sexy, dark comedy Born with Teeth, and the indie-rock hit musical Lizard Boy. Whether you’re a seasoned playgoer or brand new to live theatre, OSF promises to be an unforgettable experience.

Dine on first-class culinary delights outdoors

Downtown Ashland is home to some of the top (and tastiest) restaurants in the Northwest. Indulge in The New York Times’ top picks like Mäs, local favorites like LUNA Cafe + Mercantile, and downtown hot spots just minutes away from the Shakespeare Festival. Enjoy an array of seasonal and locally sourced foods in a warm and inviting setting.

Make time for wine (LOTS of wine)

If you are over 21, no trip to Southern Oregon is complete without a visit to one of the Rogue Valley’s renowned wineries. Explore the verdant vineyards and enjoy a stroll through (and generous sampling from) one of the many wineries in the surrounding area.

Discover the natural wonders of our parks

Nature enthusiasts, take advantage of the longer and warmer days. Enjoy the lush greenery and the serene Japanese Garden of Lithia Park, just steps away from the Oregon Shakespeare Festival. Or take the adventure a little further away and drive to majestic Crater Lake National Park, recently voted one of the most beautiful national parks in America by Travel Lens. And don’t miss the lesser-known—but much beloved—Lassen Volcanic National Park in northern California, just a few hours south of Ashland and rich with hiking, views, hot springs, and more.

Whether you’re drawn in by excellent live theatre, delicious dining, or the chance to explore nature, there is no shortage of adventure and entertainment. Plan your Ashland escape and discover for yourself the magic that awaits in Southern Oregon!