The Carrollton Ridge Community Association is incorporated within the boundaries of two old southwest Baltimore Neighorhoods: Pratt/Monroe and Bentalou/Smallwood.
- Pratt/Monroe boundaries are Frederick Ave, N. Carey Street, the B&O Railroad, Pulaski Street, and Pratt Street.
- Bentalou/Smallwood boundaries are Pulaski Street, the B & O Railroad, Catherine, Ashton, Bentalou Streets and Frederick Avenue.
Bentalou Street is named after a French calvaryman accompanying the Marquis de Lafayette to America during the revolution. Paul Bentalou settled in Baltimore as a successful shipping merchant. Smallwood Street is named after a Maryland state governor who was the southern commander of the Maryland Line during the American Revolution.
The first telephone line in Baltimore City, was installed by Mr. William Wilkens of the Wilkens Hair Factory between his plant, at the site of what is now the Westside Shopping Center, and his warehouses on Pratt Street in the late 1800s.
Guieness Book of World Records records Ohio Avenue, at the end of South Payson Street as the shortest residental street.
The 10 1/2 ft. granite obelisk monument commemorating the deeds of 5,000 Baltimoreans who served in the armed forces is the first monument in Baltimore City that was dedicated to the heroes of World War II. It was dedicated on April 25, 1943 and is located in the small triangle where Ramsay, Ashton and S. Payson Streets intersect.
Most residents worked at either one of the largest stock yards in the city located at Pratt and Payson or the Wilkens & Co hair brush factory. German-born William Wilkens, imigrated to the United States somwhere around 1833 with 18 cents to his name. He invisioned making his fortune by manufacturing hair products during the fashion-craze of false curls and chignons (false clip on hair). He worked as a trader between New Orleans and Texas to earn enough capital to invest in his enterprise; then decided on Baltimore as the plant site.
When Wilkens' plant outgrew the space he rented from the Colsen glue factory, he moved it to a 100 sq. foot site on Frederick road near the Carroll estate in a shallow valley called Snake Hollow (the current site of Westside Shopping Center). 
The location within the hollow kept down the stench of the scalding animal air laid out to dry, and the product of the vats emptied in the fields. The factory was expanded to cover 15 acres and at one time employed 700 people. The Baltimore's first telephone line was set up between the Wilkens Company plant and his warehouses on Pratt Street. There were one hundred fifty acres of surrounding acres to accomodate homes he built for his workmen. Wilkens, himself, lived in an estate house north of his plant on Frederick Avenue in the community of Shipley Hill.
The first houses were built in the fall of 1870 between Monroe and Payson streets, along Mchenry, Ramsey and Ashton. The brick of most of the houses were made from the clay extracted from the hills on either side of Wilkens Avenue. According to an article in the Baltimore Evening Sun, April 9, 1940 by Allen Will Harris, a family by the name of Sipes moved in to the second house from Monroe Street, then moved 10 years later to 1924 Wilkens Avenue. They report that there were only a dozen or so houses then. Members of the Sipes family (Henrietta, Jenny, Ella and A.R) were still living there at the time of the 1940 article. They described the "parking" or park-like median as full of flower beds with tulips and hyacinths.
Directly in front of the Snipes' house was one of the famous Wilkens statuary fountains. It was of a chubby little boy holding an umbrella over a chubby litte girl to protect her from the "rain" of the fountain. Other first families include August Steinwedel, a master mechanic for William Wilkens. His son, William A. Steinwedel, ran a drug and notions store at 2001 Wilkens Avenue in the early 1900's. The priest's house (at now St. Benedict's Church) is said to be the former home of the Steinwedel family. Dr. Norbet C. Nitsch was also still living there at the time of the article and had since 1887. He practiced medicine at 2151 Wilkens Avenue and his father was the chief buyer for the Wilkens factory.
Present day streets such as McHenry, Monroe, Bentalou and, of course, Wilkens Avenue fall within the Wilkens' land. Some of the streets were named after members of his family - Catherine (his wife), Wilhelm and McHenry (his sons). Thirty three acres of land was donated to the city by industrialist William Wilkens in 1870. It was the westside's only terraced street beyond Eutaw Place. The park like median showplaced decorated pewter urns, cupids, fountains and white maple and silver poplar trees. He wanted to name this tract of land after his son Charles to create a "fashionable Charles Street for west side workers". Unfortunately there was already a major street downtown by that name. Hence, it was named Wilkens Avenue instead.
The first section of Wilkens Avenue extended over seven blocks built eastward from Monroe street, and ran from Gilmor Street to Bentalou Street. In order to lure new companies to Baltimore, the city was persuaded to widen main arteries out of the city. Mr. Wilkens was one of the persuaders. Wilkens Avenue was designated a major cross-city highway and the park-like median was reduced to a curb.
William Wilkens was married three times and had seven children. He died in 1879 and is buried in Loudon Park Cemetary. A monument to the white horse he rode in parades, while dispensing pennies to the children, stood on Wilkens Avenue many years after his death.
Meeting the Community's Faith and Educational Needs
The Monroe Street Methodist Church, located at Monroe and Ramsay Streets, is built on land donated from the Carroll Estate. Two churches were erected to meet the needs of the growing populace along Wilkens Avenue, including a methodist church on Vincent Street. Sunday school was attended there by H. L. Mencken, the famous writer and political commentator. On a hill at Millingotn Avenue, St. Benedict's Roman Catholic Church was built. It was dedicated by Cardinal Gibbons in 1893, and a school was added later.
Blocks in Bentalou/Smallwood were predominately German before the 1900s. As late as 1980, on-sixth of the neighborhood inhabitants claimed German ancestry and a church and school were reminders of their ethnic past. St. Thomas Lutheran Church (Ramsay and Pulaski Streets) was built in 1896 to meet the faith needs of the German-speaking Lutherans. Nathaniel Ramsey opened School #96 (Ashton and Smallwood Streets) in 1895 as German-American School #6. Moses Monteiore Orthodox Jewish synagogue, named for a 19th century philanthropist, was located variously on Wilkens Avenue, Pulaski Street and Smallwood Streets from 1889 to 1957. It became part of the woodmoor Hebrew Congregation of Baltimore County. The synagogue buildings still stand on Smallwood and Pulaski Streets.