Suppose you want to attend a Tony Award-winning theater festival, explore art galleries, stroll through vineyards, go hiking, rafting, and skiing. This usually means trips to several destinations. Or you can just head to Ashland, Oregon. This Southern Oregon city is equally big on art, culture, and adventure. Add in award-winning wineries, breweries, and restaurants, and you’ve got yourself the makings of a perfect getaway.
Although Ashland has something to offer year-round, it’s perhaps most gorgeous in winter, when the snow covers the trees in Lithia Park. Here are the best things to do in Ashland, Oregon, to help you plan your visit.
Take in a play
The Oregon Shakespeare Festival was initially founded in 1935, and it’s come a long way, baby. Initially, just two works of Shakespeare were performed in a dilapidated building, but it has blossomed into a nine-month celebration of the arts, typically held between March and October. Shakespeare is still on the bill yearly, 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 rivaling anything in a larger city.
Downtown Ashland
(Brycia James via Getty Images)
Explore The Charm of Downtown Ashland
If you’re driving through the streets of Ashland, look out for deer. Although sightings of these creatures are rare in other urban areas, somewhere along the way, the deer of Ashland lost their fear of humans and saunter through the streets, yards, and sidewalks at a leisurely, oblivious gait.
Downtown Ashland has a laid-back feel reminiscent of another era. The businesses are independently owned and offer the unique charm you can only find on Main Streets without chain stores. Be sure to check out Bloomsbury Books and Three Penny Mercantile, a vintage clothing store with unique finds. Art lovers have reason to rejoice -more than 30 galleries and studios grace Ashland, showcasing work from local artists and beyond.
Get Yourself to the River
One of the best things about Ashland is its proximity to two major rivers: the Rogue and the Upper Klamath. The Rogue is scenic and gentle, and a great place for kayakers and rafters of any skill level. The Upper Klamath contains class 3 and 4 rapids, ideal for advanced rafters or even beginners 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 gourmet local food on their trips.
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 offer classes and guided trips.
Lithia Park features miles of hiking trails right downtown
(fdastudillo via Getty Images)
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 downtown. Its lovely paved walking trails lead to duck ponds, Ashland Creek, rose gardens, and idyllic Japanese gardens.
The Sterling Mine Ditch Trail in nearby Jacksonville is named after a 26-mile-long ditch constructed in 1877 to supply water to gold miners. The trail system features views of mountains, valleys, fields blanketed with velvet green and wildflowers, and historic mining tunnels.
Ashland wineries have stellar views
(Jeff Crist)
Walk the Vineyards
When most people think of Oregon wine, they think of the wineries of Willamette Valley. Although lesser known, Southern Oregon is equally worthy of a wine trip with 170 microclimates and five AVAs.
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 Weisinger Family Winery and Irvine & Roberts Vineyards. In addition to stellar vino, both wineries boast large, welcoming patios with panoramic views of the mountains.
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 beside craft cocktails. Save room for dessert, even if you usually avoid sweets – their pastry chef is legendary.
If you’re looking for something more casual, Caldera Brewing serves delicious soups, salads, and pizzas, incorporating local ingredients alongside refreshing, award-winning beer that is brewed onsite.
Hearsay Restaurant, Lounge, and Garden is one of the most fabulous restaurants in town. The interior has the atmosphere of a jazz club or speakeasy, while the patio is a tranquil paradise of trees, plants, and twinkling lights. The menu features outstanding dishes, including perfectly cooked seared scallops, house-made bread, and braised short ribs served with creamy polenta.
For a truly unique experience, you won’t want to miss Mas and its Omakase tasting menu. Focusing on local ingredients, the menu features dishes so unique and creative that they often look too delicious to eat. Ignore that each course looks like a work of art and eat it anyway—it’s worth it.
The lush patio at Hearsay Restaurant, Lounge and Garden
(Tamara Gane)
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 encounter what is quite possibly the bluest waters on earth. The lake was formed by the collapse of a volcano more than 7,700 years ago and is ringed by the remnants of the ancient mountain. It’s a great place to 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, the outdoor skating rink at Lithia Park is so magical even non-skaters bundle up to watch happy people sail by on the ice without a care in the world.
Skiers adore Mount Ashland, with four chairlifts and incredible panoramic views of the Rogue Valley. The resort offers rental equipment and lessons for beginners. There are also dedicated trails for cross-country skiing and snowshoeing.
Winchester Inn
(Jeff Crist)
Stay the Night (Or Even Longer)
There are enough activities in Ashland to warrant a trip of several days. 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 a 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 lights and luxury amenities, including an incredible spa to relax your cares away.
Also located downtown, Winchester Inn offers boutique lodging in a beautifully renovated home dating back to 1886. The graciously decorated rooms feature amenities such as 600-thread-count sateen sheets, fresh flowers, plush robes, and luxury bath amenities. The Winchester Inn features two award-winning restaurants, and a multi-course breakfast is included with your stay.
No matter where you stay in Ashland, you may experience a pang of regret when it’s time to leave. Luckily, she’ll be there to welcome you back.