Wilma (Bennett) Cipriani passed away peacefully on August 30, 2024, after a brief illness, surrounded

by her loving family. She was 90 years old. A devoted Mother, Wife, Sister, Nana, Gigi, and Friend,

she was the quiet rock for anyone who knew and loved her.

     She was born on February 2, 1934, to Wilma Ethel Little and George W. Crosby in Middletown, NY.

She graduated from Middletown High School and shortly after married her childhood sweetheart,

Leon Bennett, and began growing our wonderful and large family. She worked at Gilvan’s

Department Store in Warwick, NY as a salesperson and the best gift-wrapper they ever had! She and

Leon managed the train tours around Sterling Forest Gardens for many years. Later in life, she

reconnected with an old colleague, John J. Cipriani, they married and truly lived happily ever after

until he passed away in 1995.

     Wilma may also be remembered for her work at Horton Hospital and later Orange Regional Medical Center in Middletown, NY. She worked for the hospital for over 25 years and retired 18 years ago.

     We all have such great and varied memories of our Mom, Nana, Gigi, doing the things she loved with

and for her family and friends which meant everything to her, and we are all who we are today

because of her love and support. We loved when she made the family favorites…lasagna, big pots of

goulash, bologna salad, and breakfast for dinner, and celebrating long weekends with family at High

Point Beach, where she liked relaxing and soaking up the sun. In her earlier years she loved to

crochet afghans, as each Grandchild was born and passed that love on to some of us. She loved

riding the city bus Downtown to Woolworth’s with her Grandchildren, knowing how they loved to ring

the buzzer to get off at a stop.

     Mom looked forward to Monday nights when she would let the kids stay up late to watch Little House

on the Prairie, much later her Grandchildren turning her on to Gilmore Girls and most recently

watching reruns of the Match Game. At family get-togethers she loved watching her older

Grandchildren put together a dance routine that she would watch as long as they could keep going,

always with a big smile on her face. She enjoyed playing cards games including Skip-Bo and Rummy

or doing crossword puzzles and word search books even when at 80+ years she learned to use an

Ipad, Iphone and to play Words with Friends with some of her Grandchildren, always a worthy

opponent!

     As her Grandchildren were growing up, she got a kick out of how they loved going to her house and

looking through the big boxes of old pictures and photo albums she always had, something we all still

love to this day. She was always about making others happy, letting her Grandchildren roller-skate in

the basement in the Winter and sleigh riding down her hill in the back yard and ice skating on the

pond at the bottom of the hill. In better weather they would sit on skateboards to go down her steep

driveway, she worried but would sit and watch for as long as the kids wanted to skateboard, and ride

bikes and scooters.

     In more recent years she always wanted to stop at Twin Cone on the way home from Middletown

doctor appointments for ice cream or have her favorite afternoon snack of ice cream sandwiches,

because there’s always room for ice cream she would say!

She loved driving with her grown children to Montague, NJ to gas up her car and a trip to Perkins to

eat while WHUD was always on the radio or asking to go shopping for “1 or 2” things but always

finding things she could use….a cart full later! She was always making little memories for us along

the way. Even at 90 years young, she always remembered all the birthdays of her children, Grandchildren and

Great-Grandchildren who were so excited to receive mail with her handwriting knowing they’d be

opening a card sending lots of love and Target or Amazon gift cards!

      Wilma leaves behind beautiful memories and lots of love for her children Mark, of Kissimmee, Florida,

Kathleen Tirado and husband Joe, of Ocala, Florida, Wendy Montgomery, NY, Tim and wife, Tricia, of

Wurtsboro, NY, and Maureen Diana and fiancé John Blakeslee, of Middletown, NY. Sixteen

Grandchildren, Brian, Heather, Jessica, Kristina, Stefanie, Melanie, Jason, Brandon, Kelly, Kyle,

Kerissa, Brianna, Nina, Toni, April and Thomas. Twenty-one Great-Grandchildren, Kyra, Kramer,

Sagan, Elyssa, Emily, Ethan, Redding, Jailyn, Silas, Noah, Emma, Garner, Ella, Jasper, Adam, Tyler,

Jacob, Maddison, Charlie, Jaidia, and Amariya.

     Wilma was predeceased by her parents, sisters, Jane and Eleanor, first husband and father of her

children, Leon Bennett, beloved daughter, Shari Bennett Nelson and husband, John J. Cipriani.

Arrangements are made under the direction of Applebee-McPhillips Funeral Home., Inc.

www.applebee-mcphillips.com. Visitation will be Thursday, September 5, 2024, from 4:00-7:00 pm,

funeral services will be at Applebee-McPhillips on Friday, September 6, 2024, at 11:00 am, burial

immediately following at St. Joseph’s Cemetery, Middletown, NY.Wilma