He married Mary Ludlow. They were the parents of:

Lester Bailey 1856 - 1922
William Bailey 1858 - 1872
Ella Bailey 1860 - 1924
Mary Bailey 1866 -

1860 United States Federal Census
about Benson Bailey
Name: Benson Bailey
Age in 1860: 35
Birth Year: abt 1825
Birthplace: New York
Home in 1860: Dover, Lenawee, Michigan
Gender: Male
Post Office: Dover
Value of real estate: View Image
Household Members:
Name Age
Benson Bailey 35
Mary Bailey 36
Lester Bailey 5
William Bailey 3
Ella Bailey 3/12

1870 United States Federal Census
about Benson B Bailey
Name: Benson B Bailey
Age in 1870: 46
Birth Year: abt 1824
Birthplace: New York
Home in 1870: Jasper, Midland, Michigan
Race: White
Gender: Male
Post Office: Midland
Value of real estate: View Image
Household Members:
Name Age
Benson B Bailey 46
Mary Bailey 42
Lester Bailey 14
William Bailey 11
Ella Bailey 10
Mary Bailey 4
Allison L Bailey 66
Fredric Vibber 21
David E Welling 24
Lova S Bailey 19

1900 United States Federal Census
about Benson Briley
Name: Benson Briley
[Benson N Bailey]
Age: 76
Birth Date: Apr 1824
Birthplace: New York
Home in 1900: Jasper, Midland, Michigan
Race: White
Gender: Male
Relation to Head of House: Head
Marital Status: Widowed
Father's Birthplace: New York
Mother's Birthplace: New York
Occupation: View on Image
Neighbors: View others on page
Household Members:
Name Age
Benson Briley 76
Henry Perks 41
Ella O Perks 59
Flossi M Perks 1

1920 United States Federal Census
about Benson Bailey
Name:
Benson Bailey
Age: 95
[35]
Birth Year: abt 1825
[abt 1885]
Birthplace: New York
Home in 1920: St Louis, Gratiot, Michigan
Race: White
Gender: Male
Relation to Head of House: Father-in-law
Marital Status: Widowed
[Widow]
Father's Birthplace: New York
Mother's Birthplace: New York
Able to Read: Yes
Able to Write: Yes
Neighbors: View others on page
Household Members:
Name Age
Henry Parks 61
Ella Parks 59
Flossie Yerian 32
[33]
Benson Bailey 95
[35]