• 1906 - Leroy J Parkhurst purchased 14 Central Square from Elizabeth Winning on May 1 (deed 390/166).

• 1910 - The residence at 14 Central Square is seen at the center of the postcard below.

• 1918 - Annie L Parkhurst acquired 14 Central Square from her husband Leroy on February 7 (deed 583/543).

• 1922 - Frederick Russell purchased 14 Central Square from Annie L Parkhurst on April 8 (deed 659/387).

• 1923 - Adam MacElroy purchased 14 Central Square from Frederick Russell on August 8 (deed 689/452).

• 1926 - Tax records show there was a bakery and dwelling at 14 Central Square.

• 1934 - Tax records show there was a barber shop and dwelling at 14 Central Square.

• 1937 - Adam MacElroy died on October 8.

• 1940 - Adam's son Grant MacElroy is operating Grant's Lunch as seen in the newspaper photo below. The house (14 Central Square) is seen behind the Coca-Cola sign, the barber shop (12 Central Square) extends in front of the house to the sidewalk, and the restaurant (11 Central Square) extends from the sidewalk along the right side of the house.

• 1945 - Robert and Raymond Ducharme started doing business in the restaurant space as Bob & Ray's in October.

• 1948 - Grant R and Ellen E MacElroy were certified as owners of 11-14 Central Square and registered a property survey on January 6 (Cerificate LD7508, Plan 19883-A).
• Hormisdas J Ducharme of Lowell purchased 11-14 Central Square from Grant and Ellen MacElroy on January 7 (Certificate LD7509).

• 1949 - John R Kydd started business in the former Bob and Ray's location as Jack's Diner in November.

• 1950 - John celebrated his Diner's first anniversary in November.

• 1952 - John R and his wife Edith L Kydd purchased 11-14 Central Square from Hormisdas J Ducharme on January 3 (Cerificate LD8534).

• 1966 - Edith L Kydd died on Janurary 12.
• John R and Robert L Kydd purchased 11-14 Central Square from John R Kydd on March 4 (Certificate LD23080).

• 1969 - John R Kydd died on July 16.

• Jun 1975 - Enzio Gentile is doing business as Jack's Diner and Pizzeria.

• 1977 - Ann Lloyd is doing business as Jack's Diner in June.

• Peter and Phyllis E Demogenes of Chelmsford purchased 11-14 Central Square from Robert L Kydd on August 5 (Certificate LD22159).

• 1978 - Jean L Kydd purchased 11-14 Central Square from Peter and Phyllis E Demogenes on December 12 (Certificate LD23080).
• Ann Lloyd continued to operate Jack's Diner.

• 1982 - John Y and Diane Morgan are doing business as Jack's Diner in July.

• 1986 - The Morgans operated with a beer and wine license for five years and applied for a full liquor license. They also planned to stay open until 1 am, and expand 250 square feet into the next door space (Bob's Coins at 12 Central Square) adding about 15 more seats. The full liquor license was granted.

• 1987 - Dave J and Mary J Mansur purchased the Jack's Diner business from the Morgans, applying for a beer and wine only license in August.

• 1989 - The Mansurs decided to sell the business on April 1st and return to their previous engineering careers.

• 1991 - Lisha Ann Furtado is doing business as jack's Diner in April.

• 2000 - Barbara Hamilton is doing business as Jack's Diner in January.

• 2003 - Jack's Diner closed, and in July the Kydd family announced plans to renovate for wheelchair access and utility improvements.

• 2004 - Jamie and Kate Campos opened the Flaky Pastry in January.

• 2008 - Former Skip's waitress Jessica Kelley opened Jessie's Place in October.

• 2012 - Robert L Kydd, Jean L Kydd, and Robert L Kydd Jr, Trustees of the Kydd Family Trust II acquired 11-14 Central Square from Jean L Kydd on May 22 (Certificate LD40932).

• 2013 - The photo below shows Jessie's Place on the near corner at 11 Central Square, with Lappy Fix next door at 12 Central Square and Artizans Salon beyond at 14 Central Square.

• 2015 - Morris 1955 LLC of Venice, FL purchased 11-14 Central Square from Robert L and Jean L Kydd on July 20 (Certificate LD42394).

• 2016 - Jessie's Place closed in March, and Paraskevas Giannakas opened Rosco's Diner on October 17.

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1. All photos labeled (colorized) are black and white images edited by Fred Merriam
2. Google Earth Pro, Street View
3. Middlesex North Registry of Deeds, as listed
4. Newspaper, "Chelmsford Independent" as credited
5. Newspaper, "Chelmsford Newsweekly" as credited
6. Photo collection, Chelmsford Public Library, Flickr Account
7. Photo collection, Chelmsford Historical Society
8. Photo collection, Fred Merriam, Chelmsford