: Russ Roca

Favorite Girls Getaways in Oregon

April 27, 2018 (Updated August 6, 2019)

A getaway with friends is always great, but a trip that takes you on new adventures together is unforgettable. Fortunately in Oregon there’s no shortage of thrills, big or small, that are fit for a perfect girls getaway.

As the owner of Living Big Travel, Mary Cecchini has spent the past several years leading guided adventures around the world for families, couples, solo travelers and groups — including women-only groups. She’s an expert at helping travelers experience the best waterfalls and trails, rivers and caves, markets and culinary treats around the world.

Amid her many clients, the Portland native has loved how she’s seen women of all ages and backgrounds bond together, stretch their comfort zones and truly take time to nurture themselves. 

“The power of allowing women to see the world through the lens of another woman allows you to think more broadly,” she says of the connections women make during the trips. “It makes us more compassionate and curious. I think it does have the power to change the world.” Here are some of Cecchini’s favorite spots across the state to fit into your next outing with your favorite group of gal pals.

One of the Living Big Adventures trips involves making steamed buns at XLB. (Photo credit: Living Big Travel)

Portland Region

Cecchini is a huge fan of Forest Park — look for those less-traveled trails for some true tranquility. Treat yourself to a reward at Blue Star Donuts — their blueberry, bourbon and basil donut is legendary. Southeast Wine Collective is a great spot for people watching and mingling over a happy hour flight. You can’t go wrong having dinner nearby at any of Portland’s top restaurants on Southeast Division Street or on North Williams Avenue. Stay in the city at chic spots like the Jupiter Hotel or The Nines.

Oregon Coast

Walks on the beach are nice, but seeing the coastline on two wheels just might be better. Start fat biking with the easy Roads End Ride in Lincoln City; bike rentals are available downtown at Safari Town Surf Shop. Then stay at the retro-designed Surftides, featuring a private tennis court. If you’re ready for a bigger bike ride, consider the Otter Rock Ride in Newport with gear and shuttle service provided by Bike Newport. Plus it’s a great reason to stay at the Sylvia Beach Hotel, where each room is themed after books and authors.

Sokol Blosser Winery hosts summer wine hikes, held every Sunday morning, July through September. (Photo credit: Andréa Johnson)

Willamette Valley

Cecchini highly recommends checking out Sokol Blosser, which holds special events like wine seminars, tasting and trivia nights and chamber music. Or get a broad sampling of the world-class tasting rooms here through NW Wine Shuttle; you can buy a day pass, pick a route, jump on the shuttle at one of their designated meeting points and then hop off (and back on) at whatever stops you like. Oregon Wine Month in May is a fine time to take advantage of promotions. Cheers the day at the luxurious Atticus Hotel in McMinnville in the heart of Oregon’s wine country.

Rogue Wilderness Adventures offers raft and kayak trips on the Wild and Scenic Rogue River. (Photo credit: Kevin Wright)

Southern Oregon

It would be hard to pass up a day of exhilarating rafting on the Rogue River, or a rejuvenating spa day followed by wine tasting in Ashland or nearby Jacksonville, an artsy hub 30 minutes northwest. The Oregon Shakespeare Festival in Ashland will leave you swooning with classic plays like “As You Like it,” “Macbeth” and “All’s Well that Ends Well” running through October 2019. For a touch of class, rest your head at the Jacksonville Inn or Ashland Springs Hotel, or indulge in a soak at Lithia Springs Resort.


The glassy waters of Mirror Pond are perfect for a stand-up paddleboarding adventure.

Central Oregon

It doesn’t get much easier — or more beautiful — than stand-up paddleboarding in Bend. Rent a board from Tumalo Creek Kayak & Canoe and float on the aptly named Mirror Pond. For a bigger adventure, ride the new Crooked River Canyon Scenic Bikeway or sign up for a guided climbing trip. All that outdoor fun gets rewarded with a luxurious cabin stay at FivePine Lodge in Sisters or a night in a former classroom at McMenamins Old St. Francis School. Top it off with a beer tasting at one of the region’s many breweries.

Venture onto the Hood River County Fruit Loop to pick cherries. (Photo credit: Andréa Johnson)

Mt. Hood and the Columbia River Gorge

Venture onto the Hood River County Fruit Loop to pick cherries (from late June through early August), and explore the eastern side of the Gorge, starting at the lovely little town of Mosier, where hikes abound and you can zip through wine country on an electric bike, courtesy of MountNBarreLs guided tours. Stay in downtown Hood River at the historic Hood River Hotel, or savor the river views at the Columbia Gorge Hotel.

Eastern Oregon

Make the perfect playlist and take the ultimate road trip in Eastern Oregon. The remote southeastern corner of the state is the perfect place to recharge and reconnect with friends. When the snow melts from  Steens Mountain, explore the highest road in Oregon along the Steens Loop Tour Route, as well as a huge glacial valley and stunning vistas. Head over to the photo-worthy Alvord Desert, which is on every adventure-seeker’s bucket list. Then relax with a sunset soak at Crystal Crane Hot Springs, where you can overnight in a cozy cabin.

About The

Jen Anderson
Jen Anderson is a longtime journalist and travel writer/editor who is now Travel Oregon’s Content & Community Manager, helping to align content for visitors via social media, print and web. She’s called Oregon home for 25 years and loves finding the latest places to eat, drink and play around the state with her husband and two boys. Brewpubs, beaches and bike trails top the list.