The paper endorsed Democratic Party candidate Senator Barack Obama for President of the United States in the 2008 election cycle, and Hillary Clinton in 2016.

The Day also received NENPA's Publick Occurrences award in recognition "of outstanding journalism in 2010 for flood coverage" that included its print, photographic and web component in theday.com.

The recognition came for coverage of the flooding in late March and early April that devastated many communities in southeastern Connecticut and southern Rhode Island.

[11] In 2012, political reporter JC Reindl won the Theodore Driscoll award for an article that raised questions about Connecticut's investment in the ticket resale company TicketNetwork.

[8] In August 2018, the paper was one of 18 newspapers nationally to win grants from Poynter's Community Listening and Engagement fund.