Get Travel Southern Oregon highlights delivered to your inbox

This field is for validation purposes and should be left unchanged.

There is a lot to do in Southern Oregon! Be the first to hear about local events, seasonal highlights and a get local’s perspective on the region.


Get Wild in Winston

There are bears, hippopotamuses, and elephants that are caged in, but you get to drive around to see them living and playing in their natural habitats, and you can even get up close to meet some of them in private encounters.  When you are finished driving through the safari, stop into their FREE Safari Village where you can stroll through their botanical gardens and animal exhibits that include cheetahs, alligators, cougars and more.  There is even a children’s petting zoo!  Both of our kids have grown up going to Wildlife Safari and we all love it!  But, guess what?  There is much more to do in Winston than Wildlife Safari and we want to share those ideas with you!


With a population of less than 6000, Winston has a surprisingly abundant number of few places to taste famous Umpqua Valley wines and even a beer tasting room.  Take an afternoon to visit Freed Estate Vineyards, Wild Rose Vineyard, and HV Cellars which are right in Winston. Or you can head out of town a little bit andvisit Chateau Nonchalant Vineyard, Girardet Winery, Spangler Vineyards or Abacela Winery, home to America’s first tempranillo vineyards.  Don’t forget to stop into Lookingglass Brewery  with rotating taps that include a variety of ales and ciders at any given time.



Before you start on your wine tasting adventure stop into the eclectic Harvest store where you can pack your picnic basket with artisan cheeses, meats, and all of its accompaniments.


Not only can you buy fresh produce at Brosi’s Sugartree Farm, starting in June they offer u-pick fruit like strawberries, cherries, summer squash, green beans, peaches, peppers, tomatoes and more.  If you visit in the fall they host their Fall Festival a couple of weekends in October that offers hayrides, activities, and of course pumpkin picking!


Besides Wildlife Safari, Winston has a great community park, Riverbend Park where they offer a skate park, access to the South Umpqua River, baseball fields, and a playground.   If you visit in the summer you can also attend Riverbend Live, Winston’s summer concert series. Pack a picnic and your lawn chair and hang out for a an evening of live music and sometimes even some live theater!


Lookingglass was named in 1846 by surveyor Hoy Fluornoy, who said the beautiful green grass of the valley reflected light almost as well as mirror.  It’s a cute little community worth an afternoon of exploration.

Country store with trees
Front of Lookingglass Store
Photo credit: Lookingglass Store

Lookingglass Store

The Lookingglass Store is Douglas County’s Oldest continuously functioning business since 1852.  Stop in for a bite to eat with fresh, hot lunch choices, and house roasted coffee who’s flavor changes weekly.  They also have memorabilia to purchase and a lot of history to learn about!

Lookingglass Grange Farm Market

Located right next door to the Lookingglass store is the Grange who happens to be where their Farm Market is every Thursday, April through Christmas, 230pm to 530pm.  Peruse the wares of local artisans and crafters, enjoy freshly baked treats, home made jams and jellies, and more!

Green mossy trees

Severt Iverson Memorial Park

Pack up your lunch to take to Iverson Park down by Tenmile Creek, and when you are done eating you can explore the wooded trails.  Keep in mind there are no restrooms, but there is lots of space to run around for the kids!


Wildlife Inn is located just two miles from Wildlife Safari and many Umpqua Valley vineyards.  They offer clean, comfortable rooms that even include a sweet large enough for a family!

Winston may be the gateway to the Oregon coast but it stands on its own for at least a couple of days visit.  Don’t miss the opportunity to enjoy this lovely community in southern Oregon’s wine country and get your fix of the small town life!

Kids eating watermelon with hands behind their back.
Watermelon eating contest at the Winston Melon Festival.
Photo credit: Winston Melon Festival


Winston Summer Nite Cruise

Cruise, vendors, and entertainment every year in July.

Winston Melon Festival

Winston Melon Festival – Enjoy three days of activities in September including a parade, melon eating contest, kids activities, mud volleyball, vendors, car show, live music and more!

Winston Christmas Tree Lighting and Parade

Includes visits with Santa, cookies, and hot beverages in December.