Ashland may be famous for the Oregon Shakespeare Festival, but there is far more to this southern Oregon city than the bard and its resident deer population, which has no fear of humans. The Rogue Valley is full of stunning views, delicious restaurants, breweries, wineries, and an endless array of diverse outdoor activities.
In other words, Ashland is a city with something for everyone – and proof there’s far more to the Beaver State than Portland to the north. Here’s our list of the best things to do in Ashland, Oregon.
Arts and culture in Ashland
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 February to October every year.
Enjoy a free outdoor green show four nights a week from June till September. 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. The first Friday of every month the Ashland Galleries Association hosts the First Friday Artwalk from 5-8pm. Weekends from March through October, local craftspeople sell their wares at the outdoor Lithia Artisans Market and they can be found indoors on various locations on select dates the rest of the year.
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.
Outdoor Activities
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.
If you’ve got a hankering for a less urban adventure, outdoor playgrounds abound in the nearby Cascade-Siskiyou National Monument and Rogue River-Siskiyou National Forest. Ashland is also 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 of a world-class guide, with options for mellow floats or whitewater adventures featuring Class 4 rapids. There are even overnight packages which include glamping accommodations and gourmet meals served with local wine and beer in their gorgeous, secluded base camp.
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 700 feet of total elevation. Along the way, you’ll be treated to stunning views of the Rogue Valley, the Ashland skyline, and the Cascade Mountains.
Applegate Lake is 988 acres within the Rogue River-Siskiyou National Park, an hour’s drive from Ashland. Trails 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. Be sure to take time to look for Sasquatch along the Collings Mountain Trail, home to the world’s only Bigfoot Trap. It’s no longer in use but you can still visit to this day.
Crater Lake is a 1.5-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 U.S. 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.
Related articles: Are National Parks visitors centers worth it? Regulars weigh in
Top 10 Oregon spots for cold weather fly fishing
Enjoy the simple life at these 10 agritourism farm stays around the world
Food
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. They are particularly famous for their daily prepared desserts and craft cocktails.
Harvey’s Place is an outstanding restaurant and bar whose menu includes everything from pub fare like hamburgers and salads to upscale dishes like Diver Scallops and Filet Mignon. It’s also a great place to grab a quick drink.
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.
Drink
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 their 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. Some of the best in Ashland include Caldera Brewery and Restuarant and Standing Stone Brewery, both of which operate on green and sustainable principles.
For delicious, freshly roasted coffee, be sure to visit the Rogue Valley Roasting Co and Case Coffee Roasters when you need a caffeine fix.
Where To Stay
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, bicycles, tennis courts, shuttle service, outdoor swimming pool/hot tub, and complimentary hot 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.
