The 9 Best Things To Do In Ashland, Oregon

Explore the Charm of Downtown Ashland

If you’re driving through the streets of Ashland, be sure to look out for deer. Sightings of the creatures are rare in other urban areas, but somewhere along the way, the deer of Ashland lost their fear of humans, and they roam through the streets, yards, and sidewalks at a leisurely, oblivious gait. 

Downtown Ashland has the laid back feeling of another era. The businesses are independently-owned and offer the unique charm you can only find on a Main Street devoid of chain stores. Be sure to check out Bloomsbury Books, and Three Penny Mercantile, a vintage clothing store full of one-of-a-kind finds. Art lovers will rejoice—more than 30 galleries and studios grace Ashland with work from local artists and beyond.

Take In a Play

The Oregon Shakespeare Festival was initially founded in 1935 by, and it’s come a long way, baby. Originally just two works of Shakespeare performed in a dilapidated building, it’s blossomed into a 9-month celebration of the arts, typically held between February and October. Shakespeare is still on the bill each year, but so are modern musicals, experimental works, comedies, dramas, first-run plays, and more. You can see them all over town in outdoor venues, church basements, and three state-of-the-art venues that rival anything you’d find in a modern city.

Get Yourself to the River

One of the best things about Ashland is its proximity to not one, but two, gorgeous rivers: the Rogue and the Upper Klamath. The Rogue is scenic and gentle and a great place for kayakers and rafters at any skill level. The Upper Klamath contains class 3 and 4 rapids, and perfect for advanced rafters or even beginners who go with a guide. 

Momentum Rafting Expeditions offers seasoned guides and all the equipment you need for either river, whether you prefer a group or private trip. Arrive hungry—they are famous for serving local gourmet food on their journeys. They also have an overnight glamping option along the Upper Klamath. 

If fishing is more your speed, be sure to stop by Ashland Fly Shop for some gear and pointers; they love talking about fishing, and they also offer classes and guided trips.

Take a Hike

If you prefer land-based activities, the Grizzly Peak Trailhead is only a 12-mile drive (or hike) from Ashland. Located within the Cascade Siskiyou National Monument, the trail is 6 miles there and back, leading you to higher elevations to soak in sweeping views of downtown Ashland, the Cascade Mountains, and the Rogue Valley. 

If you’re looking for something more relaxed, Lithia Park is a 100-acre paradise located downtown filled with lovely paved walking trails that will take you by duck ponds, Ashland Creek, rose gardens, and incredible Japanese gardens. 

The Sterling Mine Ditch Trail in nearby Jacksonville takes a name from a 26-mile-long ditch constructed in 1877 to bring water to gold miners. There are several trail systems to explore here featuring views of mountains, valleys, fields blanketed with velvet green and wildflowers, and historic mining tunnels.

Walk the Vineyards

When most people think of Oregon wine, they think of the fabulous wineries of Willamette Valley. The wines of Southern Oregon, however, are a completely different animal with its own AVAs. Their offerings are more similar in style to the bolder fruit found in Walla Walla, Washington, than to other Oregon wines, but the price point is generally far more approachable. 

Boutique, family-owned operations are the norm, as are gorgeous vistas of mountains, vineyards, and families in their tasting rooms. Standout wineries to visit in Ashland include the Weisinger Family Winery, Irvine & Roberts Vineyards with their large, welcoming patio, and Bella Fiore Winery who offers tastings from their stunning chateau.

Eat Local

The Rogue Valley is famous for its farms, and perhaps there is no place better to appreciate their efforts than in a local restaurant. Larks Home Kitchen Cuisine offers a made from scratch seasonal meal featuring ingredients from local farmers and artisans served up beside craft cocktails. Be sure to save room for dessert, even if you usually avoid sweets—their pastry chef is fantastic.  

If you’re looking for something more casual, Caldera Brewing serves up delicious soups, salads, and pizzas incorporating local ingredients alongside refreshing award-winning beer brewed their onsite. 

For a truly unique experience, you won’t want to miss Mas and their Omakase tasting menu, which focuses on local ingredients and dishes so unique and creative they often look too delicious to eat. Ignore the fact that each course looks like a work of art and eat it anyway—it’s worth it.

Explore Awe-Inspiring Parks

Crater Lake National Park is an hour and a half from Ashland but well-worth the drive. Be prepared to gasp when you come face to face with what are quite possibly the bluest waters on earth. The lake was formed was by the collapse of a volcano more than 7,700 years ago, and the stone remnants of the mountain still ring it. It’s a great place to take a hike, camp, or take a scenic drive. 

The Rogue River Siskiyou National Forest is over 628,000 acres of forest, hiking trails, lakes, rivers, and mountains. If you only have a few hours to explore, spend them at the lovely Applegate Lake, which is the perfect spot for swimming, picnicking, or taking a stroll.

Play in the Snow

Winter is a special time in Ashland. Lights are strung downtown and look like something straight out of a Christmas card. Each year in December, the city holds its annual Festival of Lights.  

It’s also a fantastic opportunity for outdoor adventure. Lithia Park has an outdoor skating rink and even non-skaters love to bundle up and watch happy people fly by on ice without a care in the world. 

Skiers love Mount Ashland with its four chairlifts and incredible panoramic views of the Rogue Valley. They offer rental equipment and lessons for beginners. There are also have dedicated trails for cross country skiing and snowshoeing.

Stay the Night (or Even Longer)

There are enough activities in Ashland to warrant a trip of several days. The Ashland Hills Hotel and Suites is a fun, colorful hotel with retro decor. The rooms are spacious, and many offer gorgeous views of the mountains. There are tennis courts, a swimming pool, and hot tub, and breakfast is included with each stay. The hotel is less than a 10-minute drive from town. 

If you’d rather stay in the heart of downtown, the Ashland Springs Hotel was built in 1925 and has been beautifully and lovingly restored. The property features a European-style outdoor courtyard draped with twinkling lights and luxury amenities like an incredible spa to relax your cares away. 

Campers love Emigrant Lake County Park for its idyllic setting and convenient location just minutes from downtown. Each site has its own fire ring and picnic table. 

One thing is for sure, no matter where you stay in Ashland, you’ll experience regret when it’s time to leave. Luckily, she’ll always be there to welcome you back.