Derek R. Tolleson, Jr.

Derek R. Tolleson, Jr. obituary, Middletown, NY

Derek R. Tolleson, Jr.

Derek Tolleson, Jr. Obituary

Published by Legacy Remembers on Jul. 9, 2024.
Middletown - Derek R. Tolleson, Jr. 43, passed away unexpectedly on June 29, 2024 in Middletown, NY. He was born July 5, 1981 in Rockland County. He was the son of Derek Tolleson, Sr. and Lucretia Callahan.

Throughout Derek's life he enjoyed many things such as his love for going to stock car races, riding his quads, dirt bikes and lately motorcycles. He also enjoyed fishing and crabbing. His younger years he enjoyed camping and most of all enjoyed spending time with his loving family and friends. Derek had a special bond with his cousin Dana VanPelt and with his family of Highland Falls, NY. Derek always expressed how Dana was like a brother to him. He also had a special bond with his aunt Dawn Spatero of Stony Point, NY. Derek was a member of the Local Carpenters Union 279 in Rock Tavern, NY in which he was a carpenter. He worked with his cousin Dana with his business Exterior Concepts and his most recent he worked for the Middletown Transit Company which he drove a school bus.

Derek leaves behind his mother Lucretia Callahan of Middletown, NY. His amazing step-mother Nancy Tolleson of Port Jervis, NY. His sisters Kelly Ann Palazzo, BillieJo Griffo and Colleen Callahan. Along with his cousins Summer VanPelt and Dana VanPelt and many nieces and nephews, along with many cousins.

He is predeceased by his father Derek Tolleson, Sr. and grandparents Diane Tolleson, Julius Wallenburgh, Harold and Elizabeth Myers.

Unfortunately, there will be no services at this time. You deserved so much more when you were with us. It gives me comfort knowing you are with your dad and grandparents.

To plant trees in memory, please visit the Sympathy Store.

Sign Derek Tolleson, Jr.'s Guest Book

Not sure what to say?

December 3, 2025

William Montanye posted to the memorial.

November 1, 2025

Beau posted to the memorial.

November 16, 2024

Beau Cricketown posted to the memorial.

William Montanye

December 3, 2025

To my Big Brother Not a day goes by that I don´t think about you and talk up to you I wish you the best and we will meet again I love you and miss you Bro !!!

Beau

November 1, 2025

Always thinking of you Brother. Miss you. Love you Always,
Beau

Beau Cricketown

November 16, 2024

Derek, We all miss you so much and constantly think of you and your Great laugh. Tee Hee

Denise B

October 1, 2024

I love you Derek forever

William Montanye

September 9, 2024

William Montanye

September 9, 2024

William Montanye

September 9, 2024

I love you brother!! I can´t believe I´m just hearing about this and that we talked right before it happened and it explains why you never got back to me ride hard Buck Braaaaaappppp !!!

Cynthia DuBois

September 4, 2024

My family had the pleasure of meeting Derek as our children's bus driver. He was such a friendly, loving guy. He truly cared for our kids and as we got to know him, we truly cared about him, back. One day, my husband made him pickles and he ate the whole jar over his lunch break, haha! Today we learned of his passing and our hearts are broken for all who knew and loved him. Our bus route will never be the same.

Edward DuBois

September 4, 2024

Thanks for being such a friendly guy and making the Bruynswick Rd kids happy on the bus. We miss you!

BillieJo Griffo

July 7, 2024

BillieJo Griffo

July 7, 2024

Beau Vricketown

July 6, 2024

Love You Brother

Showing 1 - 12 of 12 results

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Sign Derek Tolleson, Jr.'s Guest Book

Not sure what to say?

December 3, 2025

William Montanye posted to the memorial.

November 1, 2025

Beau posted to the memorial.

November 16, 2024

Beau Cricketown posted to the memorial.