15 Best Things to Do in Winston, Oregon

Winston is a small city situated in Douglas County, southwestern Oregon, approximately 180 miles south of Portland and 65 miles south of Eugene with a population of 5,700.

Its typical Mediterranean climate allows for ideal weather and the ability to explore and witness what this city has to offer.

The city was incorporated in 1912 and was named after the Vice President of the United States, Adlai Stevenson’s maternal grandfather, who was also a prominent member of the Oregon community.

While Winston itself is a small city, it is surrounded by natural beauty and outdoor recreational opportunities. The Umpqua River, nearby forests, and mountains offer opportunities for hiking, fishing, and other outdoor activities.

You will not be disappointed if you take your family here for a vacation, as it provides you with access to a safari, a brewery and so much more. 

The size can also be seen as a benefit, as it can allow you a more personal experience with the surrounding area and the residents, who are always welcoming to newcomers.

This article will discuss the best 15 things to do in Winston, OR and add them to your wishlist. These places to see will only be the tip of the iceberg, but they will be sure to get you off to a good start!

Things to Do in Winston, Oregon

1. Enjoy some local beer at the Lookingglass brewery

Enjoy a locally brewed beer at the Ascension Brewing Company

Opened in 2016 with eight beers on tap, it has now added seven more taps to bring its total to 15. From Pale Ale to IPA they have lots of assortments with great aromas like coffee or chocolate making you want more.

Lookingglass Brewery provides this intimate interaction and friendly environment where you can get a firsthand experience of mingling with the locals.

It’s also conveniently located near other attractions, where you could grab a cold one and make your way over to see what else is available to you.

Of course, drink responsibly, but make sure Lookingglass is on your list of places to attend. 

2. Go see some animals at the Wildlife Safari

Wildlife Safari

A safari is a different experience than a zoo. It’s a closer look at an animal in its natural environment, and Winstons Wildlife Safari provides you with that experience.

Established in 1972 by Frank Hart whose goal was to not only put on display animals but provide a safe haven in the Pacific Northwest for rare and endangered species.

Now the safari has been classified as an AZA-accredited non-profit park. It is now dedicated to conducting research and providing education to the general public.

Ticket prices start from $17.95 for children and $23.95 for an adult for Drive Thru Safari and one visit usually takes between 60 to 90 minutes.

If you want to see rare and exotic animals, a wildlife safari is the place to go, and it will leave you speechless about what you will be seeing. 

4. Spend one day at the Morrison Rogue wilderness adventures

Arbuckle Wilderness

Now it would not be a vacation without some form of an adventure, and it would not be an Oregon adventure if you did not do something along a river like rafting.

Morrison Rogue Wilderness adventures provide you with the rise of a lifetime as you navigate across the rogue gorge and see all the beauty the trail has to offer.

They also offer patios where you can get your hands on some lunch and take in the atmosphere. They assign you to trained professionals who give you a crash course on what to expect and keep you safe.

You will have to book your place in advance and you can do this by contacting them directly on their website.

It’s an experience for the whole family that will give you a good look at the beauty the countryside has to offer. 

5. Taste some special wine at the Abacela Winery

Abacela Winery
Image source: tripadvisor.com

Now that we got the beer-drinking out of the way, it is now time to take a more classy approach, and that can be found at Abacela Winery. Abacela is located in the Umpqua Valley of southern Oregon, just minutes off Interstate 5 at exit 119.

Established in 1995, this winery seeks to present drinks that have a fine balance between grape variety and terrier. With their fruits hand-picked and processed through a flow winery, this winery provides that special taste that makes you feel like you are living the high life. 

You have different types of activities here from vineyard tours to wine-tasting experiences or even a summer music series on the patio happening every 2nd and 4th Wednesday of each month, Abacela is an amazing place to spend your day.

The tour of the property is $85 per person, it takes about 90 minutes and includes a tasting flight within the vines and a charcuterie plate back at the Vine & Wine Center. Reservations are required at least one week in advance. You can contact them by email or phone them directly.

6. Relax outside at the On the River RV Park

People playing golf

Located nearby Winston, Oregon in Myrtle Creek just 17 minutes drive from downtown, On the River RV park was established in 1995 and is a family-owned business.

Besides the RV park, there is also a full 18-hole course and especially during the summer time this place is full of people because of its location to so many great attractions.

If you have kids they will be the most thrilled since they will have lots of green space for running and playing.

The park also provides river frontage, so you can see the beautiful river streamlines by your feet. The best part of a vacation is the ability to sit and absorb everything you just experienced.

7. Visit the Oregon Aviation Historical Society Museum

If you’re interested in aviation, visit the Oregon Aviation Historical Society Museum, showcasing a collection of aircraft and aviation artifacts.

Founded in 1983, it houses an impressive collection of vintage aircraft, aviation artifacts, photographs, and memorabilia that highlight the significant role of aviation in the region’s history.

Make sure that after your visit you make a donation at the museum. These donations help them continue the restoration work and preserve the history.

8. Learn how to ride a horse at the Fagan Farms

Horse Ride Experience Tatacoa Desert

Riding horses is a tradition that has been taking place for centuries. But now, even though riding horses isn’t the main mode of transportation anymore, it is still an enjoyable experience.

Located in Myrtle Creek as well, you can now have that experience with Fagan Farms, a seven-acre property that can be found at the bottom of Robert’s Mountain. They provide horseback riding lessons with a view, and it also acts as a farm.

Other livestock can be seen grazing around within a protected perimeter. They also act as a training facility, so if you have horses or wish to see the training process take place, they provide affordable rates for both. 

9. Be adventurous for one day with Rogue Overland Adventures

The Rogue Overland 2012 Nissan Xterra PRO-4X Build | Expedition Portal

Have you ever wanted to go on an adventure where you feel deeply connected with the earth around you, finding plants and animals and getting a close look at them? Well, that is what Rogue Overland Adventures can provide you with.

Rogue is a tour service that takes you to all of the historical and cultural elements of Winston, getting you up close and personal with all the things that have made this location popular and stand out from the rest.

Established in 2017 by a young man who always wanted to be a tourist guide. They provide you with an excellent experience for you and your family to enjoy. Most of this will be done on foot, so be aware of that. They provide overnight camping, or daylight hiking, all to show you the hidden gems of the tiny city.

10. Visit the Douglas County Museum

Douglas County Museum
Image source: nrtoday.com

What Douglas County Museum looks to do is to give you an inside look into the history of the county, which includes Winston. Being Oregon’s largest natural history museum, they provide a history lesson on how settlers came across this land and cultivated it into what it is today.

Dating back more than 10,000 years with the Umpqua tribe that still calls the land home, you will be exposed to spear points, and woven quilts, you can even find pieces of the Oregon, and California Railroad.

These 7,000 physical items are held alongside 3,000 herbal specimens. It’s a snapshot into the history of this county that can make you feel like you are right at home and even create this little bond with the community that will carry on after you are gone.

Admission for visitors ranges, but usually children between 0-4 years old have free entrance, students age 5 through 17 costs $2, adults $8, and seniors and veterans can buy a ticket for $5.

11. Enjoy a day on the Umpqua River

Ohio River

The Umpqua River, located in southern Oregon, is a popular destination for travelers seeking a combination of natural beauty and outdoor recreation opportunities.

A day trip on the Umpqua River from Winston, Oregon could include renting a kayak, canoe or raft, launching your boat, and paddling downstream to enjoy the river’s scenic beauty, occasional wildlife sightings, and sandy beaches where you can stop for a picnic lunch.

You can also explore interesting sights like rapids or historic sites along the way and fish for salmon, steelhead, and trout depending on the season.

12. Enjoy the Historic Downtown Winston

The downtown district features a mix of historic buildings that have been preserved and restored, providing a nostalgic ambiance and a sense of stepping back in time.

Walking through the streets, you’ll notice well-preserved architectural styles that reflect the town’s history. Many of the buildings date back to the late 19th and early 20th centuries when Winston was a bustling hub for the timber and railroad industries.

The architecture includes a blend of Victorian, Craftsman, and other period styles, adding character and charm to the district.

One notable building in Historic Downtown Winston is the Winston Community Center, formerly known as the Winston Grammar School. This beautiful structure, constructed in 1913, now serves as a community gathering place for various events and activities.

As you explore the area, you’ll find several quaint shops, restaurants, and boutiques housed in historic buildings.

13. Explore the Winchester Dam Fish Ladder

Winchester Fish Ladder
Image source: tripadvisor.com

Located 15 mins by car from Winston, Winchester Dam Fish Ladder is a must-visit destination for travelers who are interested in the natural wonders of southern Oregon.

As an essential component of the ecosystem of the North Umpqua River, the ladder provides a unique opportunity to witness several species of fish navigate upstream past the dam.

Guests can watch the fish swim up the ladder from an observation platform located near the dam, and learn about the different species of fish and their life cycle through interpretive signs.

14. Visit a local winery

local winery

Winston, Oregon is home to several wineries that offer a diverse range of wines to suit different preferences so make sure you check all of them in advance and pick your favourite!

One of the most popular types of wine that visitors can expect to find in Winston is Pinot Noir. This red wine variety is extensively grown in Oregon and is known for its rich, fruity flavor.

Another popular wine variety that visitors can enjoy in Winston is Chardonnay. Chardonnay is grown in many regions around the world, including Oregon, and is a popular choice for those who prefer a lighter, refreshing wine.

15. Visit the Wildlife Images Rehabilitation and Education Center

Wildlife Images Rehabilitation and Education Center
Image source: wildlifeimages.org

The center is home to a variety of native wildlife species, including bears, cougars, birds of prey, reptiles, and more. Visitors can see these animals up close through guided tours of the facility, led by knowledgeable staff members and volunteers.

Wildlife Images Rehabilitation and Education Center is a popular destination for families, nature enthusiasts, and anyone interested in wildlife conservation.

The center is open to the public throughout the year, and an admission ticket for an adult is $20. All the money collected from tours is for supporting the ongoing care and rehabilitation of animals at the facility.


Size should never confuse a person. It dates back to the old saying “the best things come in small packages”. On paper Winston, Oregon may seem like a small, meaningless town, but it is towns like this that can provide the best time of your life. It can be a welcome relief from the hustle and bustle of the urban lifestyle.

To get away from the pressures of society, soak in some fresh nature and good views. It could be the recharge that so many of us desperately need. From wineries to horseback riding or kayaking, you could have everlasting memories in this phenomenal city. 

Frequently Asked Questions

How is the cost of living in Winston compared to other cities in Oregon?

Winston’s cost of living is generally lower compared to larger cities in Oregon like Portland or Eugene. Housing, utilities, and everyday expenses tend to be more affordable in Winston.

How is the weather and climate in Winston throughout the year?

Winston’s climate is humid subtropical, experiencing four distinct seasons. Summers are hot and humid, winters are cold but not severe, and spring and fall are mild.

What is the zip code for Winston Oregon?

The zip code for Winston, Oregon is 97496.

What is Winston Oregon known for?

Winston, Oregon, is known for its timber industry and beautiful natural surroundings.

What county is Winston Oregon in?

Winston, Oregon is located in Douglas County.

How far is Winston Oregon from the beach?

Winston, Oregon is approximately 50 miles from the nearest beach along the Oregon Coast.

Recommended Articles