10 of the best things to do in and around Ashland, Oregon

Let's start with one of Ashland's greatest hits – more than 20 million people have made their way to Ashland for the Oregon Shakespeare Festival since it was founded by Agnus Bowmer in 1935. An event once made up of two Shakespearan performances is now a series of contemporary and classic plays produced across three state-of-the-art theaters from March to October every year.

Enjoy a free outdoor Green Show four nights a week (Wednesday to Saturday) from May 31 to October 12. Or, if that isn’t enough for you, the Oregon Cabaret Theater is a year-round dinner theater and the Ashland New Plays Festival champions new playwrights.

Ashland also is home to more than 30 art galleries and studios, championed by Ashland Galleries Association. Time your visit for the first Friday of every month when galleries throw open their doors between 5 and 8pm for the First Friday Artwalk. On weekends from March through October, local craftspeople sell their wares at the outdoor Lithia Artisans Market.

Meanwhile, the Schneider Museum of Art at Ashland’s Southern Oregon University offers monthly visual arts exhibits in addition to its permanent collection at no charge to the public. The University is also the site of the Oregon Center for the Arts which produces live musical and theatrical events.

Ashland is one of the premier rafting and kayaking destinations in the world thanks to proximity to both the Rogue and Klamath Rivers. Companies like Momentum River Expeditions take you on a variety of trips courtesy, with options for mellow floats or whitewater adventures featuring Class 4 rapids. There are even overnight packages that include glamping accommodations and gourmet meals served with local wine and beer in a gorgeous, secluded base camp.

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Steps away from the theaters and galleries in the center of town and head to Lithia Park – 100-acres of verdant lawns, tennis/pickleball courts, sandy volleyball court, playground equipment, picnic areas, an ice skating rink in winter, and walking trails.

For hikers, Grizzly Peak Trailhead is just 12 miles east of downtown Ashland. The trailhead leads to intermediate treks of about 3 miles each way with 700ft of total elevation. Along the way, you’ll be treated to stunning views of the Rogue Valley, the Ashland skyline, and the Cascade Mountains.

Other outdoor playgrounds packed with hiking trails include the nearby Cascade-Siskiyou National Monument and Rogue River-Siskiyou National Forest, an hour’s drive from Ashland.

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Crater Lake is a 2-hour drive from Ashland and hand’s down one of the most breathtaking sights in the world. The water is so blue you’d swear it was digitally enhanced if you weren’t standing there in real-life. Created when a volcanic eruption blew the top off Mt Mazama and left an enormous crater that slowly filled with rain water, it’s the deepest lake in the US. Year-round activities including hiking 90 miles of trails, snowshoeing, snowmobiling, activities at the visitor centers, scenic drives to more than 30 overlooks, and boat and trolley tours in summer.

Planning tip: Roads close for the winter, usually at the start of November, and remain closed until May or later, depending on snowfall. Check online for road updates before you head off.

The 988-acre Applegate Lake, within Rogue River-Siskiyou National Park, has trails that run all the way around the lake’s nearly 18 miles of shoreline. Activities include mountain biking, boating, fishing, kayaking, paddleboarding, swimming, picnicking and camping. Most fun of all, perhaps, is to look for Sasquatch along the Collings Mountain Trail, home to the US's only Bigfoot Trap.

Ashland has fabulous options for nearly every budget and appetite. Wherever you choose to dine, ask for a table near the window. People-watching is one of the best activities in Ashland. The sidewalks are filled with families enjoying an evening stroll, outdoorsmen making their monthly visit to the Shop’n Kart before they disappear back into the woods, college students, and tourists making their way to the theater. The cross-section of humanity is as special as the city itself.

Lark’s Home Kitchen Cuisine is a fabulous farm-to-table restaurant with a made-from-scratch menu that celebrates local farmers, creameries, and wineries. It is particularly famous for its daily prepared desserts and craft cocktails. Stop by Harvey’s Place for a quick drink or linger for dinner – the menu includes everything from hamburgers and salads to upscale dishes like filet mignon.

No trip to Ashland would be complete without a stop by Sammich, which specializes in meal-sized Chicago-style sandwiches with house-prepared meats and sauces.

Ashland is part of the Rogue Valley AVA, which produces amazing, under-recognized wine. There’s no better way to sample them than surrounded by fabulous views at vineyard tasting rooms. Highlights include Weisinger Family Winery, Irvine and Roberts and Belle Fiore Winery.

If you’re looking for beer, Ashland is no slouch when it comes to Oregon's reputation for fields of budding hops and flowing rivers of fantastic beer. Stop by Caldera Brewery and Restaurant, which incorporates whole flower hops from Oregon in its brews.

For delicious, freshly roasted coffee, be sure to visit the Rogue Valley Roasting Co and Case Coffee Roasters when you need a caffeine fix.

Ashland Hills Hotel and Suites is located on the hill above town. The place has a fun, retro vibe and fabulous views of the mountains. Amenities include spacious rooms, a restaurant, outdoor swimming pool and continental breakfast.

If you prefer to stay right in the middle of things, Ashland Springs Hotel is a restored historic hotel, steps away from the downtown theaters. Be sure to book yourself an appointment next door at the Waterstone Spa for a soothing experience with biodynamically farmed, organic ingredients. You’ll never want to leave Ashland even after the curtain closes.