Blake Walsh

20 Best Things to Do in Winston, OR

  • Published 2023/03/08

Winston is a little city in Oregon’s Douglas County that makes up for its lack of size with history and leisure options.

Its characteristic climate provides excellent conditions for exploring everything it has to offer.

You may also consider the small size a plus because it allows you to have a more intimate encounter with the surrounding region and the locals, who are always kind to visitors.

If you bring your family here for a holiday, you won’t be bored since it offers breweries, restaurants, relaxing areas, and beautiful accommodations, among other things.

Come to Winston, Oregon, to create lasting experiences and see some nearby attractions.

Here are the best things to do at Winston, OR:

See Different Animals at Wildlife Safari

A giraffe at Wildlife Safari

Brittany Cable /

Wildlife Safari is a safari park in Winston where hundreds of animals roam freely across 615 acres, which visitors may drive through.

The park, which first opened in 1972, is Oregon’s first drive-through animal park.

A walking exhibit featuring some of the park’s smaller animals is also available.

Winstons Wildlife Safari allows you to observe wildlife in its natural habitat.

A person feeding two hippopotamus at Wildlife Safari

Tami Freed /

The place has worked as a world-renowned non-profit wildlife park committed to preservation, educational purposes, and animals in open areas for over 50 years.

Get an experience unlike any other and check out the world’s rarest, most endangered, and simply the most remarkable creatures in the world.

Have a once-in-a-lifetime adventure at Wildlife Safari!

A bald eagle at Wildlife Safari

Randy3475 /

Grab a Beer at Lookingglass Brewery

Lookingglass Brewery is committed to providing customers with a craft beer experience they will remember and love.

This brewery produces high-quality wine, cider, craft beer, and seltzer for the locals, tourists, and craft beer enthusiasts.

Try their blonde ale, pale ale, brown ale, porter, and raspberry red ale.

Lookingglass Brewery also produces seasonal ales for their customers.

This is the most fabulous location in Winston for beer enthusiasts.

Taste Delicious Mexican Dishes at Carlos Restaurante

Find original, natural, and passion-filled meals at Carlos Restaurante.

Carlos Restaurante opened in 1997 to provide the Winston region with authentic Mexican food.

The restaurant was named after the owner’s father, who is happy to share their family’s favorite recipes with new and returning customers.

From beef fajitas and enchiladas to Polle En Mole and specialty margaritas using their own tequila line, their menu teems with various delectable selections.

They provide authentic, savory dishes created with a lot of love.

Drop by for Taco Tuesday or bring the family to spend a weekend meal together.

It’s always exciting to switch it up, and try some delicious Mexican cuisine, so stop by Carlos Restaurante on your trip to Winston!

Relax at the S.W Massage Spa

S.W. Spa is an Asian spa that may help alleviate stress, treat chronic pain, and improve your overall quality of life.

They are pleased to provide authentic Asian treatment in Winston, Oregon.

S.W. Spa has massage therapists equipped to deliver various treatments in one location.

They provide a selection of cheap, tailored treatments to satisfy the demands of a wide range of clientele in a relaxing environment.

Their professional employees are ideal for helping you unwind after a hard day at work.

Treat yourself to a massage and spend a peaceful day at S.W. Spa!

Sip Fine Wine at Freed Estate Winery

Mike and Pam Freed have provided top-quality grapes to regional winemakers since founding Freed Estate Vineyards in 2000.

The family-owned winery crafts high-quality products and performs a wine-tasting service that exceeds all expectations.

Twelve acres of vineyards produce Cabernet Sauvignon, Viognier, Tempranillo, Syrah, and Merlot grapes.

One of the reasons people appreciate wine is its ability to help people relax a bit.

This is the place to visit if you have a sensitive wine palate.

Enjoy Pizza with Buddies at Abby’s Legendary Pizza

Who doesn’t want to enjoy pizza with their friends on a lovely afternoon?

Abby’s Legendary Pizza has happily served the Northwest for over 55 years.

This famous pizzeria offers excellent value in the form of pizza with 100% real cheese, toppings to the rim, and hand-rolled crusts.

This simple, long-running pizzeria serves a large selection of thin-crust or thick pizzas, sandwiches, and beverages.

See why Abby’s Legendary Pizza is one of the most popular hangout places for locals and tourists in Winston, Oregon.

Spend Time with Your Friends at Willee’s Cafe & Spirits

Willee’s Cafe & Spirits is a beautiful family restaurant with excellent cuisine, service, and daily specials.

This is a famous breakfast and lunch spot where most menu dishes are made from scratch.

Try the steaks, pasta, and a selection of tasty burgers.

Grab your favorite beer or cocktail at the lounge, which is open seven days a week.

Several televisions in the lounge broadcast Duck and Beaver games.

Weekends are highly crowded, so visit on the weekdays to appreciate the ambiance.

At Willee’s Cafe & Spirits, spend time with friends while watching the game and eating incredible meals.

Rest at the Safari Inn

Are you seeking a relaxing spot to spend the night?

The Safari Inn is easily accessible from Highway 42 or Highway 5, providing the finest accommodations in the area.

Check in to enjoy a 24-hour front desk, air conditioning and heating, HD televisions, wake-up call service, an ice machine, and various other amenities.

They ensure that their rooms are spotless and pleasant for their visitors.

Relax at Safari Inn after a long and exhausting day of touring.

Order Mexican at Muchas Gracias

Muchas Gracias is the top Mexican restaurant in two states, Oregon and Washington.

Rodolfo Sanchez De La Torre started the restaurant in 1996.

He had a great passion for cooking since he was a child working in a Californian restaurant.

Muchas Gracias is the place for high-quality Mexican cuisine.

Grab burritos, tacos, tortas, enchiladas, quesadillas, and many more Mexican dishes from the Muchas Gracias menu.

Their main goal is to serve excellent meals in all of their locations.

Drop by the Riverbend Skatepark

Are you seeking a place in Winston, Oregon, where you can rest or participate in various outdoor activities?

Riverbend Skatepark is Winston’s only skate park, with excellent waves, pipes, and rails for your ultimate skate excursion.

Pavilions, picnic tables, swings, ball fields, restrooms, and many more amenities are available in the park.

It’s the ideal spot for unwinding and making memories with friends and family.

Check Out the Plants at the Wildwood Nursery

Plants release the oxygen we breathe.

They help our emotions, creativity, and ability to unplug from technology.

Wildwood Nursery has a broad assortment of trees and shrubs, including a wide range of fruit and shade trees and more than 20 species of Japanese Maples.

Many of their garden stores are open and eager to assist you.

Wander the surroundings and admire the atmosphere of Wildwood Nursery.

Take a Dip at Harold and Sid Nichols Park

Harold and Sid Nichols Park is an underrated gem in Winston that lets you experience two attractive bodies of water—Lookingglass Creek and the South Umpqua River that’s directly connected to it.

A beautiful place, you’ll see some amazing flora and fauna at Nichols Park along with interesting terrain.

There’s a lot of available things to do here, such as taking a dip in the creek if you’re visiting during the hotter months.

You can also trek along their rugged trails and bring your dog with you.

Harold and Sid Nichosl Creek is a beautiful spot in Winston, find it along Southwest Douglas Boulevard.

Chow Down at Winston Diner and Drive-thru

Winston Diner and Drive-thru is one of the most popular fast food chains that has a special place in the heart of Winston locals.

Famous for their floats, burgers, and other classic American diner food, you can easily splurge at Winston Diner and Drive-thru because of their wide but affordable menu.

The food and service is good, and it’s a great way to have lunch or dinner if you want to try local chains in Oregon.

Winston Diner and Drive-thru also has a great atmosphere, as it’s a popular hangout place for family and friends.

Find this awesome diner along North East Main Street.

Take a Stroll at Civic Wayside Park

Civic Wayside Park is a great place to do some strolling, as there aren’t a lot of green spaces in the urban heart of Winston.

The park features great greenery and trees, giving you a much-needed break from checking out all the busy stores in Winston.

There’s plenty of shade and benches here, so you can even do picnics here with a small group.

Civic Wayside Park also has playgrounds and a pavilion, making it a great all-rounder.

Find this quaint park along Northwest Douglas Boulevard, near the North Main Street where all the hustle and bustle is at.

Find a Souvenir at Winston’s Now N Then Antiques Mall

Winston’s Now N Then Antiques Mall is a must-visit if you’re into finding quirky and unique items during your travels.

It’s one of the best places to either score a hidden gem or get a rare souvenir item that you won’t find in typical shopping malls.

Some of the most exciting aspects of Winston’s Now N Then Antiques Mall is that they have a dedicated section for “treasure” along with actual gems.

Besides that, it also doubles as a thrift store as you can find non-antique items here like clothing and essentials.

Winston’s Now N Then Antiques Mall is located along Northwest Douglas Boulevard, right across Civic Wayside Park.

Take a Breather at Winston Dillard County Park

If you need to recharge during your trip, one of the best places that’s close to the heart of the city is the Winston Dillard County Park.

It’s a nicely sized park that has amazing greenery and trees, making it one of the more quaint spots in Winston.

There are a lot of picnic benches here along with a well-maintained playground that offers a lot of fun for younger kids.

Winston Dillard County Park is also quite close to Riverbend Park, making it a great extension in your itinerary.

It’s located along Thompson Avenue.

Other Things to Do Nearby

Visit Spangler Vineyards

Spangler Vineyards is in Roseburg, Oregon, just about seven minutes away from Winston.

Pat Spangler, a former Chicago Mercantile Exchange floor trader, transformed a run-down Oregon vineyard into one of the greatest in the country.

His superb winemaking and meticulous attention to detail have helped build the winery’s reputation.

Spangler Vineyards produces a wide range of wines, with a particular emphasis on oversized, robust reds.

They specialize in stockpiling Bordeaux varieties such as Cabernet Sauvignon, Cabernet Franc, and Merlot, along with Rhone classics like Syrah, Petite Sirah, and Viognier.

Spangler Vineyards also produce unoaked Chardonnay.

Come to Spangler Vineyards and explore the area; it will make your weekend enjoyable.

Make an Adventurous Stop at On the River Golf & RV Resort

On the River Golf & RV Resort is an excellent spot to relax, which is in Myrtle Creek, Oregon, only about seven minutes from Winston.

Since 1995, On the River Golf & RV Facility has welcomed visitors to their campground and golf resort.

Their pet-friendly RV park has plenty of reasons for visitors to stop by and stay a while, from the quiet surroundings to their exquisite location near the seaside.

Settle into one of their clean, comfortable RV spaces and take in all the sights and sounds of the region.

You’ll never run out of activities with nearly 4,000 feet of river frontage, an on-site golf resort, a leisure center, a swimming hole, and a fishing pond.

Cast a line in their fishing pond, go swimming or kayaking, or meet friends in the rec room if you want a more active way to spend your weekend.

Learn to Ride a Horse at Fagan Farms

Fagan Farms LLC is a lovely seven-acre property near Robert’s Mountain’s foot in a peaceful valley.

Find it in Myrtle Creek, Oregon, 12 minutes from Winston.

Steven and Brittany Fagan, the business’s owners, work hard to restore it to its glory days as a horse boarding and training stable.

Fagan Farms LLC specializes in horseback riding classes and horse training.

Their gently sloping soil provides optimal drainage, ensuring virtually zero mud in the winter and plenty of lush grass in the summer.

Fagan Farms LLC should be on your list of locations to visit.

Learn History at Douglas County Museum of History and Natural History

The Douglas County Museum of History and Natural History has preserved and exhibited cultural and natural history artifacts from Douglas County, Oregon, for over fifty years.

It’s in Roseburg, Oregon, ten minutes from Winston.

The Douglas County Museum tells the epic narrative of over 10,000 years of civilization and the spectacular natural beauty of the Umpqua River Valley and the Cascade Mountains.

Find the remaining Oregon and California Railroad terminals and the family’s Oregon Trail cabin among the relics.

You’ll also see skillfully made baskets and archaic spear points.

Create lasting memories at the Douglas County Museum of History & Natural History by learning about history.

Final Thoughts

Winston, Oregon, might be a little city, but tourist destinations like these can give you the time of your life.

Create lifelong experiences in this magnificent city, from the park, spas, and vineyards to different delectable cuisines.

De-stress from modern life by taking in the fresh air and beautiful scenery at Winston, Oregon.

Book your trip today!

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