New Haven History from the Sidewalk


By Mary M. Donohue

(c) Connecticut Explored Inc., Spring 2023

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“The saga of Grand Avenue is a tapestry of stories, compelling stories that intersect with other stories, layered on and woven into yet other stories, sometimes in the history of a single unassuming building.”

  • Aaron Goode, project historian and committee member, speaking at the Grand Avenue tour book launch, as quoted by Paul Bass in the New Haven Independent on May 9, 2002

The Ethnic Heritage Center (EHC) of New Haven’s four published walking tour guides take the user on a trip through more than 300 years of the city’s development. As a preservationist, I always believed that if you knew the history of a place, it would make you care more about it. And if you uncovered the history, you’d feel inspired by the stories of the people who came before you. The Walk New Haven project of the EHC was honored as a Connecticut History Game Changer by Connecticut Explored in Fall 2022.

Streetscapes change over time, with each generation leaving its mark. Beginning with the publication of the EHC’s first book about downtown and downtown north in 2016, each volume reveals a neighborhood’s social history and architectural character with well-illustrated entries. Pooling their resources, the city’s five ethnic historical societies—Jewish, African American, Italian, Ukrainian, and Irish—have built complex narratives for each neighborhood that show the diversity present in the city from the beginning. The histories of these ethnic and racial groups are intertwined with those of the buildings. Historic photographs sourced from

museum collections, private collectors, and city residents show neighborhoods across decades and add personality to the entries. Users can also find interactive maps and entries on the website.

The information below is taken from the tour guides.


Grand Avenue (State Street to East Street, 1830-1970)

The Grand Avenue area has often been seen as an appendage of other areas, most often Wooster Square. But it has had its own identity since the 1830s. First-generation free Blacks in a subsection called New Liberia, Eastern European Jews, Irish and Italian immigrants, and first-generation Puerto Rican transplants settled there to build homes, places of worship, and businesses. Much was torn down by the Urban Renewal program in the 1960s and 1970s  to make room for a highway.

Although the buildings are no longer standing, the history of the Artizan Street School and Lillian’s Paradise celebrate the contributions of Black women. The Artizan Street School was one of several segregated New Haven grammar schools for African Americans in the mid-1800s, led by teacher Sarah Wilson, an African American woman giving instruction in her home to students of various ages. The classes were often overcrowded. According to school records, in 1861 Wilson had only 93 spaces available in her makeshift “classroom” but taught 120 students, tutoring them in shifts because of the limited space.

Almost 100 years later, in 1946, Lillian Benford Lumpkin, a Black woman from Alabama who came to the city during the Great Migration, opened a restaurant and nightclub. In its heyday Lillian’s Paradise was dubbed “Connecticut’s Smartest Night Club” and listed in the Green Book, a road guide for African American motorists that let people of color know the club was a safe place for them to visit. Many jazz greats from the 1940s and 1950s performed there.

Italian bakeries and meat markets provided a taste of home for New Haven’s Italian community. Lucibello’s Pastry Shop at 935 Grand Avenue continues to make life sweet for its customers.

Jacob Heller and Louis Mandelbaum were first cousins who arrived together in the United States in 1837 from Bavaria in southern Germany. Around 1840 they started a family business, a small dry goods store at the northeast corner of Grand and State streets. The Heller and Mandelbaum store was a modest operation, and probably less well known than the building’s second-floor occupant. Above the dry goods store in 1840 Congregation Mishkan Israel, the first Jewish religious society in Connecticut and the oldest continuous synagogue congregation in New England, was established.

Downtown and Downtown North

The first site in the Downtown New Haven tour is the New Haven Green, established in 1640 as the central green in New Haven’s unusual nine-square city plan. The city’s role as a retail hub can be seen in the entries for the region’s grand department stores, some of which have been demolished, such as Shartenberg’s, Howowitz Brothers, and Mendel & Freedman. New Haven’s outsized entertainment history is evident in the Shubert Theater, built in 1914 and used as a theater of choice to try out new Broadway productions, including almost all of the Rodgers & Hammerstein musicals.  For another type of entertainment, New Haven is home to the sixth longest-running St. Patrick’s Day parade in the United States.

Downtown North is home to links to New Haven’s earliest Jewish community. The William Pinto House belonged to the son of Jacob Pinto, a Sephardic-descent Jew who arrived in New Haven in 1758. William served in the American Revolutionary War as an officers’ secretary. The high-style homes of scientists Stephen J. Maher, an expert on tuberculosis, and Lafayette Mendel, one of the discoverers of the nutritive value of vitamins, are still standing.

Lower Dixwell

The Dixwell neighborhood was home to a mixed population of German, Italian, Jewish, and African American residents. During the period of southern migration to the north during the 1910s, the African American population grew steadily and by 1930 made up 50 percent, and by 1960 75 percent, of the neighborhood. This decade saw the Italian, Jewish, and German families relocate to other areas of greater New Haven. Although the Dixwell neighborhood went through redevelopment and construction during the 1960s, it now supports a library, banks, health-care facilities, successful businesses, churches, and a resilient population.

Wooster Square

Pizza and cherry blossoms immediately come to mind when Wooster Square is mentioned. But the area was originally known as New Township, a bustling seaport area. In the 1820s and 1930s, Slineyville was an Irish area east of Wooster Square, and New Guinea, founded by African American builder William Lanson, was also here. Italians seeking a new life began to settle in Wooster Square in the 1880s, establishing a macaroni factory, five bakeries, pastry shops and specialty meat shops. Wooster Square’s world-famous pizzerias draw visitors today.

Rhoda Samuel, project coordinator, believes that success of the project “shows how important each ethnic and racial group has been to New Haven and how they have contributed to a strong community.”


The following Walk New Haven guided our books, along with interactive maps and site information, are available for purchase at

  • Downtown and Downtown North
  • Grand Avenue (State Street to East Street, 1830-1970)
  • Lower Dixwell
  • Wooster Square



Mary M. Donohue is an architectural historian and served as the assistant publisher of Connecticut Explored for a decade. She is the co-host and producer of Grating the Nutmeg, the podcast of Connecticut history.



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