[17] The Berkshire County Eagle, however, remained a part of the paper, as a weekly section within the Wednesday edition of the daily, until 24 June 1953.

In a 1973 Time magazine article about The Eagle, then Boston Globe editor Thomas Winship was quoted as calling The Eagle the best newspaper “of its size in the country.” The article mentions that the paper carried occasional book reviews from Berkshire County residents such as James MacGregor Burns and William L. Shirer.

)[19] Press critic Ben Bagdikian in 1972 stated that there were only three great newspapers in the world, each in its own way: The New York Times, Le Monde, and The Berkshire Eagle.

Failing to find a white knight to help them weather the fiscal storm that ensued, in 1995 the Millers sold their holdings to MediaNews Group, a company founded by William Dean Singleton of Denver, Colorado.

[25] Later under MediaNews management, as newspapers in general faced increasing financial challenges there were multiple rounds of staff reductions as various functions were consolidated into centralized locations on a regional or national basis.

[20] In April 2016, a team of local investors bought The Eagle, along with its Vermont sister newspapers the Bennington Banner, Brattleboro Reformer and Manchester Journal, from Digital First Media (DFM), the new name of MediaNews Group.

The investor team consisted of former Visa Inc. President John C. "Hans" Morris, local retired judge Fredric D. Rutberg, M&T Bank Chairman Robert G. Wilmers and Stanford Lipsey, former publisher of The Buffalo News and former owner of the Omaha Sun newspaper group of Nebraska.

By improving the quality and quantity of the content in our publications, we expect to increase our readership which will, in turn, increase our revenues, and ensure the future of these publications.”[20][30] Under the new owners, The Eagle has been able to hire additional newsroom staff, expanded its investigative team, and has launched new content including a Sunday arts-focused section called Landscapes.

They established a community advisory board including journalists Linda Greenhouse and Donald Morrison, and authors Simon Winchester and Elizabeth Kolbert, all of whom have Berkshire area connections, and representatives of many local non-profits and businesses.

[34][29] In 2019, The Eagle's owners purchased a weekly newspaper, the Southern Berkshire Shopper's Guide, based in Great Barrington, Massachusetts.

[62][63] In 2023, Eagle editorial page editor David Coffey received the Carmage Walls Commentary Prize for newspapers under 35,000 in circulation, for editorials taking to task the Springfield (Massachusetts) Roman Catholic Diocese for demanding an Eagle reporter's notes for a series of stories about sexual abuse allegations against a powerful former bishop.

These positions include a general predisposition toward free expression, as well as leaning toward progressive ideas, environmental conservation, the encouragement of innovation and entrepreneurship, and the promotion of tourism and cultural entities."