The daily calendar at Whispering Winds Retirement Community is packed with a variety of activities including bingo, cardio drumming, birthday parties, chair volleyball, mimosas & watercolor class, bridge club, shopping trips, live music and so much more.
Whispering Winds, which opened in 2003, has 148 residents and about 60 staff members. Source readers voted it Best Senior Living Community (for the third time) and as runner-up this year for Best Place to Work (over 50 employees).
“I think a lot of it has to do with we are privately owned,” General Manager Carrie Kasch says when asked why the retirement community garnered enough votes to launch it to the top. Whispering Winds is managed by Dharma Healthcare Management, which manages five retirement communities in Oregon with locations in Bend, Eugene and Medford. Rooms range from studio to two-bedroom, with five cottages behind the main building.
“I think as soon as you walk into Whispering Winds you can feel the difference,” Angela Vanderpool, VP of Operations, adds. “Everyone’s here because they care and love the residents.”
It’s an independent living community for anyone 55 or older. There is no medical staff. The overall mission is to enjoy life with friends. “We’re going to take care of their meals, activities, socialization, driving services, housekeeping, maintenance — all the things that can allow them just to live their best life,” Vanderpool explains.
“A lot of them (residents) refer to it like being on a cruise ship, like being on vacation. They move in and everything is taken care of,” says Kasch. “I think also learning new things…One of the members was like, ‘I can’t believe I’m 90 and I’m finally learning new things.’ She was learning to do calligraphy that she’s always wanted to learn.”
The main building on NE Conners Avenue has a cozy fireside room for residents to socialize in or read a book, a gym with regular fitness programs, a hydroponic garden, a spacious dining area with a private, fancier dining room for special occasions and a courtyard with a pond. In addition, field trips are offered to places like the Tower Theater, hiking, local lakes and horse races. Sometimes longer trips are planned to locations like Hawaii or the Monterey Bay Aquarium.
But even with all that, both Kasch and Vanderpool agree, the biggest draw is the cuisine.
“The dining room is just like a restaurant here. It’s open all day long. They can come in any time,” Vanderpool says. “We have a full menu with more than 30 entrees, daily specials, a full salad bar, two soups. We are known for our food. Our food is delicious and we are all about food around here!”
“I think the hydroponic garden too is a really nice touch,” Kasch adds. “We use some of those items in our salad bar and the chef uses (it) too.”
It’s a community where everyone is invested.
“We have some very long-term staff members. I’ve been here for 23 years,” Kasch says. “We have a hospitality director who’s been here 15 years. Our office manager has been here 13.”
“I’ve been here 18 years and can’t imagine doing anything else,” Vanderpool agrees. “What makes it special is we all love it.”
Runner-up: Touchmark
Whispering Winds
2920 NE Conners Ave Ste 100, Bend
whisperingwinds.info/
541-312-9690
This article appears in Best of Central Oregon 2026 and the Source August 13, 2026.
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