Libby Rupp

Finding A Home

Libby Rupp moved to Kendal at Longwood after working at the Westtown School as a teacher and administrator for many years. When she retired from Westtown, a former student invited her to live in a home in West Chester, which Libby did for several years. When the house was being sold, Libby knew she only wanted to move once more, and Kendal-Crosslands Communities was her first choice. 

Libby had looked at many senior living communities throughout the Philadelphia area, trying to find what would be the best fit. She did have a history with Kendal-Crosslands- her parents were among the first residents when the community was built.  So she felt pretty comfortable choosing Kendal at Longwood- it was familiar and it kept her in proximity to friends and professionals like doctors and dentists.

Finding Your Community

Libby believes strongly in the  Quaker values – Community, Integrity, Diversity, Stewardship and more. The values that she appreciated so much while teaching at a Quaker-based school are present at Kendal-Crosslands as well. “While I am not a Quaker myself, the strong moral foundation and support for people in the community is the same here as it was at Westtown,” Libby said. “There was a freedom when I was teaching to help people explore ideas and reflect on what we were learning together- there was no rush to finish a chapter by Thursday. That same sense of shared values we had at Westtown is similar here. I feel very at home here and we have wonderful, deep discussions, where people really listen and respond to each other, rather than look at a conversation as a contest to see who wins.”

Community Organization for the Community

One of the great assets at Kendal-Crosslands Communities is the Resident’s Association. The Residents Association on each campus supports different committees which organize the activities on campus- and everyone participates in what interests them most. Libby volunteers with the Flower Committee, organizing the floral displays across the Community and spends some of her time in the weaving room, using the looms to work on projects, as well as participating in classes and other projects across the community.

Making Good Choices- and Taking Your Time

The divider bookcase built-in Libby Chose for her Studio creates different spaces in a small footprint

Libby’s studio home at Kendal at Longwood is cozy, not cramped- and Libby has done a great job at separating spaces so it feels like a full apartment. 

“I took my time and started out here, without bringing much other than my bed- and then added the things I wanted and needed, rather than bringing everything and feeling cramped. I had this wonderful divider and bookcase constructed which separates my bedroom from my living space, and the three-season room patio gives me an extra room I use almost all year long.” As we spoke, Libby’s two cats were soaking up the warm, fall sunshine in the three seasons room, and stretched, to start to meander into the living room, looking for some affection, and maybe a few treats. Her small dog sat on a chair beside her, curled up and as content as Libby is here at Kendal at Longwood. “I have everything everyone else here has, just in a smaller footprint, and it’s just perfect for me.”

With the divider she added, Libby’s studio feels like a full apartment, with a bedroom, living room, kitchen and bath- just more compact.  The storage and closets in the Studio are large, giving plenty of space for things.  

Libby approached the issue strategically, making sure she made good choices to maximize her space and her privacy- so she can have people over, without feeling they are in her bedroom.

“There are accommodations people make for living in a small space. I can have four people over for dinner before I have to start rearranging all the furniture.  For larger groups, we can meet up in the Center or at the library. There are lots of options.” 

Family History and Family Choices

“My parents lived at Kendal for many years and had many friends in the community. When Dad passed away, my mother had a support team to help every step of the way. There were people to answer questions, deal with insurance, paperwork, clothes- everything. My mom didn’t have to go through the trauma of selling the family home and moving- all she really needed to do was grieve for him, right alongside people who also knew him and loved him.”

“They had the type of relationship where you would expect the surviving spouse to go quickly without their other half. Mom lived another 12 years and thrived, with so many things to do, surrounded by a community that supported her every step of the way. It made it easier for the four of us, their children as well, knowing she was always among close friends and well cared for. We give Kendal full credit for making the last 12 years of her life wonderful.”

Libby continued, “It’s kind of funny, actually, since Mom was the one who resisted coming to Kendal- she said she didn’t want to live in a “fishbowl”, but Dad insisted. And as it turned out, that community “fishbowl” was what helped her most when Dad was no longer there.”

Studios Are Affordable for Many

Living in the studio cottages at Kendal is an affordable option to be part of a caring community that has served generations of families.  Click here to learn more about pricing. The residents curate the community through the Residents Association, and this creates a culture that remains true to its core values, while still evolving with the changing needs and interests of current Residents, always reflecting a sense of ‘This is great- but it can be even better’ ethos. Along with the excellent continuing care, residents here live longer, more productive lives in a community that truly cares and nurtures the spirit in each other.

You can take a virtual tour of one of our model studio cottages below.

Want to Learn More about Kendal-Crosslands Communities?


If you want to learn more about our community and how we are redefining the experience of aging, just click the button below to download a digital version of our Brochure. You’ll see what truly sets us apart from other retirement and Life Plan communities. In addition to our amazing 500 acre campus and all the amenities, you’ll find dynamic and engaged residents like Libby who truly make our community special.