Explore the Best of Ashland, Oregon

Ashland is renowned for its vibrant cultural scene, particularly the Oregon Shakespeare Festival. However, there is so much more to this Southern Oregon city beyond the Bard and its friendly deer population.

Surrounded by the stunning Rogue Valley, Ashland offers breathtaking views, a variety of exceptional breweries and wineries, and an endless array of outdoor activities. Within the city limits, you can explore numerous art galleries, beautiful parks, and top-notch dining options—evidence that Ashland has much to offer beyond just what lies further north in Portland.

Here’s a curated list of the best things to experience in Ashland, Oregon.

Experience Ashland’s Thriving Theater Scene

One of the highlights of visiting Ashland is its theater scene. Since its inception in 1935, over 20 million visitors have been captivated by the Oregon Shakespeare Festival, which has transformed from a two-play event into a series of contemporary and classic productions staged in three state-of-the-art theaters from March until October each year.

Join in the fun with the free outdoor Green Show that occurs four nights a week (Wednesday to Saturday) from late May until mid-October. For those who desire a different theatrical experience, the Oregon Cabaret Theater offers a year-round dining and performance experience, while the Ashland New Plays Festival nurtures new playwrights.

Support Local Arts and Crafts

Ashland boasts over 30 art galleries and studios, supported by a vibrant local arts community. Plan your visit for the first Friday of each month to experience the First Friday Artwalk, where galleries open their doors from 5 PM to 8 PM. Don’t miss the opportunity to visit the Lithia Artisans Market on weekends from March to October, where local artisans showcase and sell their crafts.

Discover Creativity at Southern Oregon University

The Schneider Museum of Art, located at Southern Oregon University, frequently hosts monthly visual art exhibits and provides free access to its permanent collection. Additionally, the campus is home to the Oregon Center for the Arts, which presents a diverse range of live musical and theatrical performances.

Rafting and Kayaking Adventures

Ashland is a premier destination for rafting and kayaking, thanks to its proximity to the Rogue and Klamath Rivers. Various local companies offer exciting trips, from serene floats to exhilarating whitewater adventures with Class 4 rapids. For a unique experience, consider overnight packages that combine glamping accommodations with gourmet meals, accompanied by local wines and beers in a picturesque setting.

Stroll Through Lithia Park

Just a short walk from the downtown theaters and galleries lies Lithia Park, a stunning 100-acre green space featuring lush lawns, tennis and pickleball courts, picnic areas, and picturesque walking trails. Whether you prefer leisurely walks or engaging in recreational activities, this park is a lovely spot to unwind.

Hiking Trails Around Ashland

For hiking enthusiasts, Grizzly Peak Trailhead, located just 12 miles east of downtown, offers exhilarating trails with stunning views of the Rogue Valley and the Cascade Mountains. The area is further enriched by nearby hiking options in the Cascade-Siskiyou National Monument and Rogue River-Siskiyou National Forest, both of which are perfect for outdoor exploration.

A Scenic Drive to Crater Lake

Crater Lake, just a two-hour drive from Ashland, is one of the most awe-inspiring places in the world. Its astonishingly blue water, the deepest lake in the US, was formed by the collapse of Mount Mazama following a volcanic eruption. The park offers year-round activities, including hiking, snowshoeing, and summer boat tours, making it a must-visit destination all year round.

Search for Bigfoot at Applegate Lake

The scenic Applegate Lake within the Rogue River-Siskiyou National Park offers nearly 18 miles of shoreline for hiking, mountain biking, boating, fishing, and more. Undoubtedly, one of the highlights is the thrill of searching for Bigfoot along the Collings Mountain Trail, known for being home to the country’s only Bigfoot Trap.

Discover Ashland’s Culinary Delights

Ashland features diverse dining options to suit any budget. The pedestrian-friendly streets provide ample opportunities for people-watching while enjoying delicious meals. Lark’s Home Kitchen Cuisine is a standout farm-to-table restaurant that offers a menu crafted from fresh, local ingredients. For a casual outing, Harvey’s Place provides a fantastic mix of comfort food and upscale cuisine.

Taste Local Wines, Beers, and Coffees

As part of the Rogue Valley AVA, Ashland is home to some outstanding yet lesser-known wineries. Enjoy tasting sessions at scenic vineyards such as Weisinger Family Winery and Irvine and Roberts. Beer enthusiasts will appreciate places like Caldera Brewery, which incorporates local hops into its flavorful brews. For caffeine lovers, Rogue Valley Roasting Co and Case Coffee Roasters are must-visit spots to enjoy freshly roasted coffee.

Planning Tips: Accommodation in Ashland

For a pleasant stay, consider Ashland Hills Hotel and Suites, located on a hillside with stunning mountain views and ample amenities, including an outdoor pool. Alternatively, the Ashland Springs Hotel, a beautifully restored historic hotel, places you steps away from downtown attractions and local theaters, making it an ideal choice for visitors.

This article was first published Jan 2, 2020, and updated Apr 27, 2024.