23 Best & Fun Things Do in Ashland (Oregon)

Looking for the best & fun things to do in Ashland, Oregon?

Sitting at the foothills of the great Cascade Mountains in the Rogue Valley is Ashland, Oregon, just north of the California border. The city boasts of the travels of pioneers and prospectors, the rich history of the indigenous Shasta people, and the tales of trappers and hunters.

Ashland is an abundance of art and culture and also a dual blend of simplicity and sophistication. The wineries and vineyards, shopping malls, painted landscape, museums, and warmth of the community establish Ashland as a must-visit area.

For a fun vacation time in Ashland, let’s explore the best things to do in Ashland, Oregon

Things to Do in Ashland

1. Don’t miss the Oregon Shakespeare Festival

Oregon Shakespeare Festival
Credits: Oregon Shakespeare Festival / Flickr
Oregon Shakespeare Festival

In 1935, Angus Bowmer carved out a legendary repertory theatre, and since then, the Oregon Shakespeare Festival has been in the spotlight. The Oregon Shakespeare Festival is one of the top attractions of Ashland.

It is a trio combo of theatres set amongst the beautiful pine forests of a really mountainous region. Every year, these theatres record an audience of 400,000.

With a season that runs from February until the end of October, the festival offers five to eleven play performances that rotate six days a week.

Be a part of this season, as you would enjoy the off-stage excitement of interactive learning through workshops and classes. Thanks to the book Shakespeare Festivals Around the World, the Oregon Shakespeare Festival is regarded as a major festival, so don’t miss out!

Address: 15 S. Pioneer St. Ashland, OR 97520.

2. Explore the world of arts at Schneider Museum of Art

Schneider Museum of Art
Credits: Mike Linksvayer / Flickr
Schneider Museum of Art

Established at the Oregon University, the Schneider Museum of Art is a combined effort of the school and the community, which came to reality thanks to the benevolence of Bill and Florence Schneider.

Today, the museum is a core part of the university’s commitment to appreciating and learning about visual arts.

Schneider Museum of Art offers knowledge of art to the academia and, in extension, the Ashland community through striking exhibits and engaging programs.

Visitors are welcome to the museum all year round with a changing schedule of exhibits featuring contemporary and historical aspects of arts.

All these call the attention of renowned artists all over the world. Admission is free of charge, and guided tours are offered o Tuesdays.

Address: 555 Indiana Street, Ashland, OR 97520

3. See Long Walk Vineyard

Long Walk Vineyard
Credits: Rostislav_Sedlacek / Shutterstock

Long Walk Vineyard started in 2001, going through a journey that encompasses the historic Valley View Orchard situated in southern Oregon’s Rogue Valley.

They are a certified vineyard that harvests and sort their products by hand to produce superb Rhone-style wines crafted to pattern old-world Southern France.

You would also enjoy the Tasting House at Long Walk Vineyard as they serve guests an exceptional selection of single varietals, unmatched blends, and Province-style rosés.

You have will also see an on-site orchard called the Valley View Orchard. It is a commercial grower of fruits and also has a u-pick stand.

Here varieties of apples, apricots, cherries, and pears are produced and immediately place for sale in the Valley View Orchard Farm Store.

Address: 1800 N. Valley View Road, Ashland, OR 97520.

4. Exploring Lithia Park is one of the Top Things to do in Ashland

Lithia Park
Credits: Tiffany Rucker / Shutterstock
Lithia Park

Lithia Park is the biggest park in Ashland, and thanks to the American Planning Association, it is listed as one of the best Great American Spaces.

This park occupies 100 acres and spreads across a rich, active green landscape.

The park offers visitors sufficient family-friendly activities. Guests will find pickball and tennis courts mottled around the century-old landmarks, as well as playgrounds, picnic spots, and sandball and volleyball.

A Japanese garden, ornate fountains complement the Ashland creek, and duck ponds, coupled with the awesome beauty of a formal rose garden and the sycamore groves.

Lithia Park has Trail guides who lead patrons on a self-guided tour of this precious jewel in Ashland.

A visit here makes what to do in Ashland, Oregon for a fun exploration, consider an addition to your Ashland things to do list.

Ashland, OR 97520

5. Cool Off in the Rogue River

Rogue River
Credits: John Brueske / Shutterstock
Rogue River

The Rogue River offers numerous opportunities for guests to explore through the broad array of water adventures like canoeing, boating, kayaking, fishing, swimming, white water rafting, and more.

These recreational water sports allow you to experience the unbelievable Rogue valley wilderness making it a top attraction in Ashland.

The river offers exceptional views of crystalline water and the surrounding rich forests. Noah’s River Adventures, Indigo Creek Outfitters, and Momentum River Expeditions are the businesses most preferred by tourists to offer these water sports services.

You can check any of them out.

6. Enjoy a Cabaret act at Oregon Cabaret Theatre

Oregon Cabaret Theatre
Credits: WOU Theatre / Flickr
Oregon Cabaret Theatre

A visit to Oregon Cabaret Theatre is one of the best fun things to do in Ashland. This theatre stands out on the corner of a lofty Ashland landmark called First and Hargadine.

Originally constructed in 1911, this building was Ashland’s First Baptist Church before it was sold in the late 1960s.

The building started falling into disrepair, and in 1982, Craig Hudson painstakingly began restorations in a bid to bring the building back to its former glory and even more.

This move led to the creation of the Oregon Cabaret Theatre. Renovations include the theatre accouterments and crystal chandelier rescued by Hudson from a movie house in Lansdale, Pennsylvania.

Turrently, Oregon Cabaret Theatre puts up an annual performance of five shows with some selections taken from their list of fifteen original productions.

Address: 241 Hargadine St, Ashland, OR 97520.

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7. Winter activities at Mount Ashland

Mount Ashland Ski
Credits: maciej / Shutterstock
Mount Ashland Ski

One thing is special about Mount Ashland, and that’s the fact that it has the highest peak in the entire Siskiyou mountain range. So, trying something here would sure be in the good record books.

Located 20.4 miles from Ashland City, the Mt. Ashland ski area is great during the summer.

It offers awesome opportunities for skiing, mountain biking, snowboarding, snowshoeing, cross country skiing, sledding, snow hiking, and lots of winter recreation activities.

Not only that, during the summer, it becomes a popular destination for hiking, reunions, star gazing, and weddings. In all four seasons, Mt. Ashland offers magnificent views, so don’t miss out!

8. Let the kids enjoy ScienceWorks Hands-on Museum

ScienceWorks Hands on Museum
Credits: Oregon Department of Transportation / Flickr
MScienceWorks Hands on Museum/center>

Another interesting place to visit in Ashland, especially for science enthusiasts, is the ScienceWorks Hands-on Museum. It is a 26,000 square foot museum that provides an interactive experience to visitors.

ScienceWorks Hands-on Museum teaches visitors of all ages about a lot of sciences through programs and activities as well as indoor and outdoor hands-on exhibits.

They can explore Discovery Island for young science lovers, especially for kids five years old and below, with features like the Thatched Hut Reading Nook and Crawlers Cove.

ScienceWorks is a well-known field trip destination, and it organizes classes and camps all through the year. You will be exposed to the amazing laws of physics, the wonders of space, and the complexities of anatomy.

This is one of the top things to do in Ashland, Oregon, At ScienceWorks, science is brought to life.

 Address: 1500 E. Main St, Ashland, OR 97520,

9. Enjoy the North Mountain Park Nature Centre

The beautiful Bear Creek situates this North Mountain Park Nature Centre. This center has a playground, beautiful gardens, hiking trails, ponds, soccer fields, picnic areas, softball fields, and baseball fields.

You are going to have a great time, with various activities and areas available for you to enjoy. You will see ducks, fishes, turtles, and several other creatures at the creek. It is perfect for a nice summer picnic, swimming, and hiking

The nature center is open from 8.30 am to 4.30 pm, during weekdays, while the grounds are open from dawn to dusk every day.

Exploring this Nature center makes what to do in Ashland for a fun time, for some outdoor time, this should make your list of things to do in Ashland, Oregon.

Address: 620 N Mountain Ave, Ashland, OR 97520.

10. Check out the Belle Fiore Estate & Winery

Belle Fiore Estate & Winery
Credits: Ievgenii Meyer / Shutterstock

While in Ashland, it is expedient you satisfy your taste and hunger and not just the satisfaction but doing that in an engaging environment. That’s why you should try the Belle Fiore Estate & Winery.

Belle Fiore Estate & Winery is an appealing Mediterranean chateau and Pavilion that delights guests’ palates by the savory flavors of food and wine pairings they offer.

You would love the tasting room, which is built of classic Italiante architecture and offers magnificent views of the mountains.

Entering the Chateau Tasting Room would see you meet an elegant style of French architecture braced with scenic landscape views.

The sounds of live music every night would sweep you off your feet as you dine upon awesome cuisine blended with a rich wine selection.

You will love the art gallery at Belle Fiore Winery too. As proof of the love of art and community support, it features different local artists every month.

Definitely one of the unique things to do in Ashland, Oregon, a must-add to your list of Ashland Oregon activities.

Address: 100 Belle Fiore Lane, Ashland, OR 97520.

11. Crater Lake National Park is one of the Top Things to Do near Ashland, Oregon

Crater Lake National Park
Credits: Kris Wiktor / Shutterstock
Crater Lake National Park

Crater Lake National Park is located 77 miles from Ashland city, and driving to this place will take around 1½ hours.

Though not in Ashland, it is one of the most popular tourist attractions in all of southern Oregon, and it draws several visitors in their thousands each year.

This lake was created about 7800 years when a volcanic eruption caused a mountain to collapse, thereby forming a crater that was later filled by melting snow and rains.

This lake is the deepest and clearest in the entire country. It is also known for its depth and crystalline waters.

Visitors can explore a wide range of recreational activities in the area, including camping, cross country skiing, hiking, cycling, snowshoeing, and skiing. Swimming is also possible but restricted to some designated areas.

12. Learn of Irvine & Roberts Vineyards

Irvine & Roberts Vineyards
Credits: View Apart / Shutterstock

One special place in Ashland is Irvine & Roberts Vineyards. In 2007, Irvine & Roberts Vineyards planted their foundational vines on an 80-acre highland ranch.

After Doug and Dionne Irvine discovered they had found a dystopia terroir for ultra-premium Pinot Chardonnay and noir production.

The Irvine & Roberts Vineyards came into play as a family-owned business after a coalition with Doug’s sister Kelly and her husband, Duane Roberts.

Its location is of high altitude and provides the grapes with eastward slopes, choicest weather conditions, and extraordinary soil.

This causes wine to be produced with intensity, balance, and exquisite flavor. Check out the environmentally-friendly techniques applied in growing these grapes, as well as the exceptional quality of their wine.

Address: 1614 Emigrant Creek Road, Ashland, OR 97520.

13. Shop at Lithia Artisans Market

Lithia Artisans Market
Credits: Lithia Artisans Market / Facebook
Lithia Artisans Market

One of the top fun things to do in Ashland, Oregon is some shopping time at Lithia Artisans Market.

Located close to Lithia Park in downtown Ashland, Lithia Artisans Market is an outdoor artisans’ market available for you to shop on the weekend.

With over 35 stalls, you cab purchase handcrafted jewelry, glasswork, pottery, photographs, fiber art, home décor, and sketches by artists and artisans from the region.

Other features include lie sketches and live music. The market is open from March to October on Saturdays (10 am – 6 pm) and on Sundays (11 am – 5 pm).

14. See Emigrant Lake

Emigrant Lake
Credits: Ahturner / Shutterstock
Emigrant Lake

Emigrant Lake lies outside of Ashland, just at the southern point of the majestic Rogue Valley.

It was first created in 1924 as a reservoir of the Emigrant Creek with an arch dam that regulates the waters for irrigation and also the prevention of flooding.

As a well-loved destination for nature enthusiasts, Emigrant Lake offers year-round camping at one of 32 RV hook-ups. You would also love to experience their bumpy summer camp at any of the forty basic campsites.

The Group Campground accommodates 100 people offering an oversized campfire ring, a horseshoe pit, and picnic tables. There are boat ramps at Emigrant Lake available for water sports lovers and fishers all year round and beaches for sunbathers and swimmers.

Address: 5505 Highway 66, Ashland, OR 97520.

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15. Things to do in Ashland for Movie Lovers: Watch a Movie Marathon

Ashland Independent Film Festival
Credits: Al Case / Flickr
Ashland Independent Film Festival

Every year, an annual Ashland Independent Film Festival is organized in April, and it lasts for five days. This festival presents more than a hundred local and international short films, features, and documentaries.

The Historic Ashland Armory, the Ashland Street Cinemas, and the Varsity Theatre are the three venues in which the festival is hosted. This sees movie fanatics troop in their thousands every year to these theatres so as to attend this event.

Ashland has another popular film festival called Varsity World Film Week. It runs through seven days in October.

16. Enjoy fine wine at Dana Campbell Vineyards

Dana Campbell Vineyards
Credits: True life photography / Shutterstock

Nestled in the foothills of the Cascade Mountains, Dana Campbell Vineyards is one lovely feature of the Ashland community and Southern Oregon. The first vines were planted under the expertise of some local vineyard managers in 2006.

Dana Campbell Vineyards produces a nice selection of distinctive wines. The land is meticulously prepared before planting operations of the vineyard to make sure that the best-quality grapes are grown.

In February 2013, Dana Campbell Vineyards had their tasting room opened, and they continue improving so as to give their valued wine connoisseurs and patrons the warmest welcoming experience.

Address: 1320 N Mountain Ave, Ashland, OR 97520.

17. What to Do in Ashland for some Theater time: Visit Oregon Centre for the Arts

Oregon Centre for the Arts
Credits: Stokkete / Shutterstock

Oregon Centre for the Arts is a department of the Southern Oregon University. All through the year, this center organizes various artistic live performances in Ashland.

These performances include short film screenings, musical concerts, and more. They are very popular among tourists as well as natives of Ashland

18. Taste great wine at Weisinger Family Winery

Weisinger Family Winery
Credits: pilipphoto / Shutterstock

In 1979, Weisinger Family Winery cultivated their first wine grapes of the Ashland area and since then, the winery has grown to be a household name in Ashland.

Then, in 1988, John Weisinger started the inceptive winery with a tasting room the following spring. By virtue of his young family, this small dream of John was grown into a legacy that he has handed over to Eric, his eldest child.

Weisinger Family Winery is in the continuous business of producing small lots of wine with assiduous management of the vineyard leading to the creation of the best, locally-grown fruits.

For some wine time, Weisinger Family Winery is a perfect addition to your bucket list of things to do in Ashland, Oregon.

Address: 3150 Siskiyou Blvd, Ashland, OR 97520

19. Read books at Ashland Library

Carnegie Library in Ashland
Credits: Underawesternsky / Shutterstock
Carnegie Library in Ashland

The Ashland Library is a regularly visited public space in Ashland and stands out thanks to its numerous valuable resources and its aesthetic design.

This Carnegie Library has a stately courthouse design which is surrounded by landscaped grounds and a still exterior. The inside takes care of a quiet study as it has natural light, high ceilings, fast and free internet.

In addition to the books, newspapers, and magazines, there are other popular community resources like public meeting rooms, kids’ storytelling times, and computer stations.

Address: 2196, 410 Siskiyou Blvd, Ashland, Oregon.

20. Check out Ashland Artisan Emporium

Ashland Artisan Emporium
Credits: Lynn Ceteras Huerta / Flickr
Ashland Artisan Emporium

Ashland Artisan Emporium is a 17,000 sq ft cumulation of merchandise. It showcases more than local vendors, artisans, and collectors. It is one of the top things to do in Ashland, Oregon.

The store is family-owned, and while being the brain box of a loving father, it is now owned and managed by his daughter Michelle who’s accomplishment keeps the spirit her alive.

At Ashland Artisan Emporium, there is an eclectic blend of crafts, vintage clothes, antique collectibles, home furnishings, and more.

Ashland Artisan Emporium is open every day of the week and records daily new inventory arrives. New vendors are also welcomed to joining their teeming community of artisans. You would enjoy the company of the friendly staff merged with the expressive skill of each vendor’s booth.

They have gone on to build a name as the premier shopping hot spot in Ashland.

Address: 1670 Ashland Street, Ashland, OR 97520.

21. Visit Grizzly Peak Winery

Grizzly Peak Winery
Credits: Delpixel / Shutterstock

Grizzly Peak Winery was started by Al and Viginia Silbowitz to push for their passion for winemaking.

Winemaking is a craft, and the Silbowitz have the belief that great wines are meant to be shared with family and friends in love, thereby creating a bond understood only by wine lovers.

Gizzly Peak Winery is an ample 40-acres of breathtaking natural beauty. The surrounding mountainous landscape of Mt. Ashland and Grizzly Peak add to the elegance of this location. It is also ideal for weddings and other special events.

Throughout the year, guests are treated to great music and entertainment, including Auto Europa – a free classic European car show in Ashland. So, if you are looking for a place to sit and have a sip with a loved one, it should be at Grizzly Peak Winery.

Address: 1600 E. Nevada Street, Ashland, OR 97520.

22. Relax at Peerless Hotel Restaurant & Bar

The Peerless Hotel
Credits: The Peerless Hotel / Facebook
The Peerless Hotel

Originally constructed in 1904, Peerless Rooms Building was a lodging house for the working-class, and this is where the Peerless Hotel Restaurant & Bar resides.

Crissy Barnett Donovan purchased the building in 1991 after years of being vacant. She started a thorough two-year restoration, including the preservation of a 1915 painted sign involving a Coca-Cola advertisement.

And in 2007, the Peerless Restaurant & Bar was honored with the “Most Beautiful Restaurant” in all of Oregon.

This favorite restaurant has a lively atmosphere and elegance in its garden seatings, two dining rooms, and a cozy bar. Aside from the charming garden, the Peerless Hotel provides guests the affinity of a boutique hotel blended with the sweetness of bed and breakfast.

Address: 265 4th St., Ashland, OR 97520.

23. Go practical at Gathering Glass Studio

Gathering Glass Studio
Credits: Yasemin Yurtman Candemir / Shutterstock

Gathering Glass Studio is situated in the historic Railroad District of Ashland, only a few meters away from Main Street. It is one of the best places to visit in Ashland, especially for art lovers.

Established by shop owner and skilled artist Keith Gabor, Gathering Glass Studio is famous for making radiant-blown art glass creations. The studio practically demonstrates the various methods required to produce top-quality American-made works of art.

Gathering Glass Studio has available classes for aspiring glasswork artists, thereby making it a hot shop. At the gallery are displays of the finest caliber pieces created by Keith and any of the brilliant guest artists of the studio.

Visitors can collude with the artists to craft custom-made orders for home decor, keepsakes, or unique gifts.

This is one of the best things to do in Ashland, Oregon, consider an addition to your list of Ashland Oregon attractions to visit.

Address: 322 N. Pioneer Street, Ashland, OR 97520

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Plan a Trip to Ashland

Ashland, just like we’ve seen, is the artistic and cultural axis of southern Oregon. It is filled with unending greenery and natural beauty.

You will marvel at the majestic mountain ranges, breathtaking lakes, dense forests, beautiful creeks, crystalline rivers, magical waterfalls, and the many outdoor recreational activities.

So, start planning your next vacation to be in this awesome city. This piece can always serve as an aid anytime, so pin it.