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Alan F. Skelley Sr.

May 10, 1933 ~ March 16, 2023 (age 89) 89 Years Old
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Alan F. Skelley Sr. 1933 – 2023.

Al Skelley Sr., lovingly known as “Bump” to close family and friends, died Thursday afternoon, March 16, 2023 at 89 years old. Alan is predeceased by his loving wife of 60 years, Virginia Bailey Skelley. Alan was born May 10, 1933 to parents Robert H. Skelley III and Roberta Skelley in Lynn, MA.

Al matriculated from Melrose High School to Bridgton Academy in Bridgton, ME. After his graduation from Bridgton Academy, Al served in the United States Army during the Korean War.

In 1956, Alan met and married Virginia “Gina” Bailey of Wolfeboro, NH. In the early years of their marriage, Al committed to furthering his education, and earned his Bachelor of Science in 1959 from the University of New Hampshire, where Gina Skelley was also an alumna. Both Al and Gina held the University of New Hampshire close to their hearts; their eldest son, “Chip” as well as his wife Deb (Hale), their daughter Kaitlyn, and Al’s grandson Dougie are all alumnus of UNH. You could regularly see Al and Gina at field hockey, football, and hockey games year in and year out. Al held immense pride in the Gina Bailey Skelley Athletic Fund, which was spearheaded by Jere Lundholm ’53 and his wife Harriet Forkey ’54, in honor of Al’s late wife, Gina Skelley. This scholarship has been awarded to a field hockey player annually at UNH since the Fall of 2016.

Alan and Gina moved to Wolfeboro, NH in the early 1960s to raise a family and help assist with the family restaurant, “Bailey’s”, which they eventually owned and operated. They owed and managed Bailey’s Dockside Restaurant for 22 years, and Bailey’s Restaurant for 40 years; it became a place the Skelley family called home and made many wonderful memories and friendships. Al was a staple at Bailey’s and was responsible for teaching many Wolfeboro area residents that there is, in fact, a right and a wrong way to write an order ticket. His staunch attention to detail and commitment to a standard of high quality helped Bailey’s thrive and made it a cornerstone of Wolfeboro summers. Later in his life, Al could be seen working alongside his oldest son “Chip” in the kitchen at Skelley’s Market in both Wolfeboro and Moultonborough, and continued to make Bailey’s Delicious Homemade Fudge, Butterscotch, and Penuche’s sauces for Bailey’s Bubble, where the team affectionately dubbed him the “Sauce Boss.”

Alan was an integral part of the Wolfeboro community. He served as the Wolfeboro Police Commissioner from 1969-1973; was a member of the Lions Club; served on the Board of Directors of the Kingswood Trust & Savings Bank; and coached many middle school football and high school ski teams at the Kingswood Schools.

Alan shared a deep love of skiing, golf, and athletics with his wife Gina. For 20 years, Al and Gina assisted Penny Pitou on her ski trips to the Alps, which Gina shared were “some of the best times of her life.” Both Alan and Gina built a lifelong friendship with Penny and Pam during this time. Alan’s love for skiing was not restricted to the Swiss Alps, however. He was also a Professional Ski Instructor of America (PSIA), presenter for the Boston Globe Ski Shows, and part owner of Boston Hill Ski Area in Andover, MA and Mt. Whittier in Ossipee, NH. In the summers, Al and Gina played golf religiously – you could regularly find Al and Gina participating in tournaments with friends, playing a “quick” 18 holes, or simply putting and chipping in the front lawn of their home. Alan was also responsible for sharing his knowledge and deep love of the game with his grandsons Allie, Tad, and Erik – even if they never managed to hit the ball quite as straight or as far as Bump could.

One of the greatest joys in Alan’s life was his family. He is survived by his four sons, 12 grandchildren, and 8 great-grandchildren. Chip Skelley and his wife Deb (Hale) of Wolfeboro, NH, their children Allie and wife Stefanie, their sons Fitzy (Alan IV) and Wellsy (Joseph Wells), and daughter Livia – Kaitlyn and her husband Andy, their daughters Bailey and Padley – Tad and his wife Josie and their daughters Madden and Colbie. Rick Skelley, Wolfeboro, NH and his children Presleigh and her fiancé Michael Ronsivalli, Hanna and Erick. Douglas Skelley and his wife Sheila (Maddock) of Wolfeboro, NH and their children Doug and his wife Margot, and their son Maddock, and daughters Johanne, Emily and Virginia. David and his wife Heather (Kinmond) of Hamburg, NY and his children Josh and Rebecca, and Heather’s daughter Gianna Cubeddu. Al was an institution on the Kingswood sidelines, and loved nothing more than watching his grandchildren compete in their many athletic events including football games, ski races, hockey games, field hockey games, and many more. Supporting their children and grandchildren was something Al and Gina both cherished.

Alan was the third of 6 children – he is predeceased by Robert H Skelley IV, Richard Skelley, Roberta Skelley, and Roy Skelley. He is survived by Dean Skelley.

The family would like to thank the Veteran’s Administration for the loving and compassionate care for Bump throughout his later years, and for the kindhearted and benevolent care at Huggins Hospital received during his final days.

Upon Alan’s wishes, there will be calling hours at Lord Funeral Home June 2 from 6:00 – 8:00pm, and a Celebration of Life at Lakeview Cemetery at 10:00am Saturday, June 3.

The family wishes memorial contributions be made to the Gina Bailey Skelley ’52 Family Athletic Scholarship Fund at the University of New Hampshire and mailed to UNH Foundation, Elliott Alumni Center, 9 Edgewood Road, Durham, NH 03824.

To send flowers to the family or plant a tree in memory of Alan F. Skelley Sr., please visit our floral store.


June 2, 2023

6:00 PM to 8:00 PM
Lord Funeral Home, Wolfeboro, NH
Rt. 28
Wolfeboro, New Hampshire 03894
Guaranteed delivery before the Visitation begins

Graveside Service
June 3, 2023

10:00 AM
Lakeview Cemetery
North Main Street
Wolfeboro, NH, NH 03894
Guaranteed delivery before the Graveside Service begins

Online Memory & Photo Sharing Event
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In Loving Memory Of

Alan Skelley Sr.

May 10, 1933-March 16, 2023

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Online Memory & Photo Sharing Event
Online Event


In Loving Memory Of

Alan Skelley Sr.

May 10, 1933-March 16, 2023

Look inside to read what others have shared

Family and friends are coming together online to create a special keepsake. Every memory left on the online obituary will be automatically included in the book.   


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