In 1961, Giuffrida, a 43 year old butcher from Lawrence, Massachusetts, purchased a small bar on busy Route 1 in Saugus for $7,000 and converted it into a 125-seat steakhouse.

The Boston Globe’s Anthony Spinazzola described the Hilltop's interior decor as "old ranch modern with wooden Indians, stone fireplaces, buffalo heads, Victorian lighting fixtures, plastic flowers and color that runs to expected browns and reds".

[4] In the 1970s, the Campbell Soup Company attempted to create a chain of Hilltop-like restaurants and hired Giuffrida as a consultant.

[5] The New York Times described the Hilltop as "America's largest restaurant, both in number of customers served and sales volume" in 1987.

[10] In 1988, Giuffrida sold the corporation that owned and operated Hilltop Steak House to John Swansburg.

[13] In 1992, Hilltop Steak House Inc. filed a registration statement with the Securities Exchange Commission for an initial public offering.

[19] Hilltop's early menu was small and focused on beef and a few other meat options as well as lobster pie and a few appetizers, desserts, and kids meals.

Giuffrida and Mack principal Charles S. Magliozzi considered many Western designs, including cowboys and cattle, before settling on the cactus.

[22] In 2006, an Essex County jury found that the Hilltop's function department illegally steered tip money to managers and wrongfully terminated four waitresses after they complained.

Soon thereafter, the two sides went to court over privileges established in the original lease, which entitled the Giuffridas and their guests to free food and drink and access to the first available table for life, which were lost following the sale.

[26] In 2018, AvalonBay Communities redeveloped the 14 acre property into “Avalon at Hilltop" - a residential and commercial development that includes 280 luxury apartments, two restaurants, a dry cleaner, and a hair salon.

[26] The sign still stands today and is frequently seen on Boston TV traffic reports covering that area of Route 1.