17 Best Things to Do in Ashland, OR

By VI Staff on January 2, 2020

Ashland, Oregon sits at the foothills of the noble Cascade Mountains in the Rogue Valley just north of the California border. Filled with the rich history of the indiginous Shasta people, the tales of hunters and trappers, and the travels of pioneers and prospectors, Ashland is a plethora of art and culture as well as a dichotomy of sophistication and simplicity. The painted landscape and warmth of the community make Ashland a treasure to behold.

1.Oregon Shakespeare Festival

The Oregon Shakespeare Festival has been taking the stage since 1935 when Angus Bowmer created a legendary repertory theatre. Set amongst the glorious pine forests of the mountainous region, this trio of theatres brings in an annual audience of 400,000. The season runs from February through the end of October offering performances of five to eleven plays on rotation six days a week. The season is filled with excitement off stage as well with interactive learning through classes and workshops. The Oregon Shakespeare Festival is considered to be a major festival according to the book Shakespeare Festivals Around the World.

15 S. Pioneer St. Ashland, OR 97520, Phone: 800-219-8161

2.Lithia Park

Lithia Park is the largest park in Ashland and is listed as one of the best Great American Spaces by the American Planning Association. Spread across 100-acres of lush, vibrant green landscape, the park provides visitors with family-friendly activities. Speckled around the century-old landmarks, guests will find tennis and pickleball courts, sand volleyball, playgrounds, and picnic spots. Ornate fountains, duck ponds, and a Japanese garden complement Ashland creek and all the wondrous beauty of the sycamore groves and formal rose garden. Lithia Park Trail guide will lead patrons on a self-guided tour of Ashland’s precious jewel in the middle of forested canyonland.

Ashland, OR 97520

3.Oregon Cabaret Theatre

Oregon Cabaret Theatre stands tall on the corner of First and Hargadine, an exalted landmark of Ashland. The building was originally constructed in 1911 as Ashland’s First Baptist Church until it was sold in the late 1960s and began to fall into disrepair. In 1982, Craig Hudson began painstaking restorations to bring the building back to its former glory and beyond by creating the Oregon Cabaret Theatre. Renovations included the striking crystal chandelier and theatre accoutrements Hudson rescued from a movie house in Lansdale, Pennsylvania. Oregon Cabaret Theatre now performs five shows a year with some selections from their list of 15 original productions.

241 Hargadine St, Ashland, OR 97520, Phone: 541-488-2902

4.ScienceWorks Hands-on Museum

ScienceWorks Hands-on Museum is an interactive experience for science enthusiasts of all ages. The 26,000 square foot museum teaches visitors about a multitude of sciences with activities and programs as well as hands-on exhibits, both indoors and out. Young science lovers can explore Discovery Island, exclusively for children 5 years-old and under with features like Crawlers Cove and the Thatched Hut Reading Nook. ScienceWorks is a popular field trip destination and offers camps and classes throughout the year. From the intricacies of anatomy to the fascinating laws of physics and the wonders of space, ScienceWorks brings science to life.

1500 E. Main St, Ashland, OR 97520, Phone: 541-482-6767

5.Belle Fiore Estate & Winery

Belle Fiore Estate & Winery is an enchanting Mediterranean chateau and Pavillion where guests’ palates are delighted by the savory flavors of wine and food pairings. The tasting room at the Pavillion is built of classic Italiante architecture with breathtaking views of the mountains. The Chateau Tasting Room is a graceful style of French architecture with picturesque landscape views. Visitors will be swept away by the sounds of live music nightly as they dine upon elegant cuisine and a rich selection of wines. Belle Fiore Winery’s love of art inspired their art gallery which supports the community by featuring a different local artist each month.

100 Belle Fiore Lane, Ashland, OR 97520, Phone: 541-552-4900

6.Irvine & Roberts Vineyards

Irvine & Roberts Vineyards planted their first vines in 2007 on an 80-acre highland ranch when Doug and Dionne Irvine learned they had found a utopian terroir for producing ultra-premium Pinot noir and Chardonnay. Together with Doug’s sister Kelly and her husband Duane Roberts, the family-owned Irvine & Roberts Vineyards was born. Their high-altitude location provides the grapes with extraordinary soil, choice weather conditions, and eastward slopes producing wines with exquisite flavor, intensity, and balance. Irvine & Roberts Vineyards create wines with love and compassion by practicing sustainable farming in the rich hills of the Cascade Mountains. These environmentally-friendly growing techniques will ensure the longevity of the land and the remarkable quality of their wine.

1614 Emigrant Creek Road, Ashland, OR 97520, Phone: 541-482-9383

7.Emigrant Lake

Emigrant Lake sits at the southern point of the majestic Rogue Valley just outside of Ashland. This reservoir of the Emigrant Creek was first created in 1924 with an arch damn to regulate the waters for irrigation and prevention of flooding. Emigrant Lake is a popular destination for nature lovers offering year-round camping at one of 32 RV hook-ups or experience a rugged summer of camping at any of the 40 basic campsites. The Group Campground serves up to 100 people providing picnic tables, an oversized campfire ring, and a horseshoe pit. Emigrant Lake has boat ramps available year-round for fishermen and water sport enthusiasts and beaches for swimmers and sunbathers.

5505 Highway 66, Ashland, OR 97520 Phone: 541-774-8183

8.Dana Campbell Vineyards

Dana Campbell Vineyards is tucked into the foothills of the Cascade Mountains of Southern Oregon near the community of Ashland. Following the expertise of other local vineyard managers, the first vines took root in 2006. By maximizing the fertile slopes and preparing for the effects of weather, Dana Campbell Vineyards produces a fine selection of unique wines. Meticulous preparation of the land is performed before planting expansions of the vineyard to ensure the highest-quality wine grapes. Dana Campbell Vineyards opened their tasting room in February of 2013 and continue making improvements to create the warmest welcoming experience for their valued patrons and wine connoisseurs.

1320 N Mountain Ave, Ashland, OR 97520, Phone: 541-482-3798

9.Weisinger Family Winery

Weisinger Family Winery cultivated the pioneering wine grapes of the Ashland area in 1979. John Weisinger then founded the initial winery in 1988 with a tasting room the following spring. With the help of his young family, John grew his small dream into a legacy he has handed off to his eldest child, Eric. Weisinger Family Winery continues to produce small lots of wine with fastidious management of the vineyards and allowing the terroir to create the highest-quality, locally-grown fruits. The Weisinger family believes wine is a subjective experience that no two people encounter the same way. Wine is a form of art that can leave an impression on your very being.

3150 Siskiyou Blvd, Ashland, OR 97520, Phone: 541-488-5989

10.Ashland Artisan Emporium

Ashland Artisan Emporium showcases over 200 local vendors, collectors, and craftsmen in a 17,000 square foot treasure trove of merchandise. The store came from the vision of a loving father and is now owned by his daughter Michelle who’s success keeps her father’s spirit alive. Ashland Artisan Emporium carries an eclectic mix of home furnishings, vintage clothes, crafts, antique collectables, and more. They welcome new vendors to join their growing community of scrupulous artisans. Ashland Artisan Emporium is open 7 days a week with new inventory arriving daily. Their friendly, helpful staff combined with the creative flair of each vendor’s booth has built a solid reputation as Ashland’s premier shopping hot spot.

1670 Ashland Street, Ashland, OR 97520, Phone: 541-708-0577

11.Grizzly Peak Winery

Grizzly Peak Winery was created when Al and Viginia Silbowitz discovered their passion for the craft of wine making. The Silbowitz believe great wines are meant to be shared lovingly with family and friends creating a bond and a connection only wine lovers understand. Gizzly Peak Winery is a spacious 40-acres of awe inspiring natural beauty surrounded by the mountainous landscape of Grizzly Peak and Mt. Ashland. This wonderous location is ideal for weddings, special events, or just to sit and sip with a friend. Music and entertainment await guests throughout the year including Auto Europa, Ashland’s free classic European car show.

1600 E. Nevada Street, Ashland, OR 97520, Phone: 541-482-5700

12.Gathering Glass Studio

Gathering Glass Studio forges radiant blown art glass creations by skilled artist and shop owner Keith Gabor. The studio demonstrates the various techniques required to make high quality American made works of art. Classes are available in Gathering Glass Studio’s hotshop for aspiring glasswork artists. The gallery showcases the finest caliber pieces created by Keith or one of the studio’s other brilliant glass artists. Guests can collaborate with the artists to conceive custom made orders for unique gifts, home decor, or keepsakes. Gathering Glass Studio is located in the historic Railroad District of Ashland, just steps away from Main Street.

322 N. Pioneer Street, Ashland, OR 97520, Phone: 541-488-4738

13.Schneider Museum of Art

Schneider Museum of Art was established at the Southern Oregon University in a collaborative effort by the school and the community thanks to the generosity of Bill and Florence Schneider. The museum has become an integral part of the university’s commitment to visual arts education and appreciation. Schneider Museum of Art delivers knowledge of art to both academia and the community of Ashland with bold exhibits and engaging programs. The museum is open to the public year-round with a revolvong schedule of exhibits featuring historical and contemporary aspects of art to highlight renowned artists around the globe. Admission is free with guided tours on Tuesdays, closed Sundays.

555 Indiana Street, Ashland, OR 97520, Phone: 541-552-6245

14.Long Walk Vineyard

Long Walk Vineyard began their journey in 2001 encompassing the historic Valley View Orchard in southern Oregon’s Rogue Valley. The certified organic vineyards are harvested and sorted by hand to produce exquisite Rhone-style wines crafted in the manner of old-world Southern France. Long Walk Vineyard’s Tasting House serves guests a phenominal selection of single varietals, unparalleled blends, and Province-style rosés. On-site is the Valley View Orchard, a commercial grower of fruits and a u-pick farm stand. They produce a variety of cherries, apples, peaches, apricots, and pears and are available for immediate purchase in the Valley View Orchard Farm Store.

1800 N. Valley View Road, Ashland, OR 97520, Phone: 541-552-0534

15.Peerless Hotel Restaurant & Bar

Peerless Hotel Restaurant & Bar resides in the Peerless Rooms Building originally constructed in 1904 as a rooming house for the working-class. After years of vacancy, the building was bought by Crissy Barnett Donovan in 1991. She initiated an extensive 2-year restoration including the preservation of a painted sign from 1915 containing a Coca-Cola advertisement. The Peerless Restaurant & Bar received the honor of Most Beautiful Restaurant in all of Oregon in 2017. This top-rated restaurant has sophistication and a lively atmosphere in its two dining rooms, cozy bar, and seating in the garden. Beyond the beguiling garden, the Peerless Hotel offers guests the intimacy of a boutique hotel combined with the quaintness of a bed and breakfast.

243 4th St., Ashland, OR 97520, Phone: 541-488-1082

16.Alchemy Restaurant & Bar

Alchemy Restaurant & Bar emulates the science and philosophy of alchemy by taking individual ingredients and transmutating them into the greatest amalgamated form. The chefs strive to take basic components of spices, oils, and seasonings mixed with vibrant colors of fresh produce and matched with savory meats and seafood to develop the Magnum Opus of cuisine. The refined staff takes pride in their shared passion for creating masterful works of art that represent the balance that is alchemy. The bar offers an abundant menu of attentively selected spirits and a wine list of local hidden jewels in company with famous labels.

35 S. 2nd St, Ashland, OR 97520, Phone: 541-488-1115

17.Martolli’s Hand-Tossed Pizza

Martolli’s Hand-Tossed Pizza opened in Ashland when two long time friends and pizza lovers, Mark and Brad, were enticed by the arts and culture of the area. Their passion for using fresh local ingredients and made from scratch doughs, sauces, and salad dressings reflect the ideals of the deep rooted community. Guests select from prime ingredients to mix and match the perfect pizza creation. Martolli’s serves up an everchanging selection of beers, wines, and non-alcoholic specialty drinks that will tantalize the finest palets. This family-friendly music loving restaurant offers two locations for folks to gather and enjoy a custom made hand-tossed pizza in the heart of mountainscape paradise.

38 East Main, Historic City Plaza, Ashland, OR 97520, Phone: 541-482-1918

1469 Siskiyou Boulevard, Ashland, OR 97520, Phone: 541-482-1913