Ann “Heady Lady” Di Benedetto

Ann M. Di Benedetto was Cleveland’s unforgettable “Heady Lady,” a milliner whose passion for fashion transformed a personal love of hats into a celebrated cultural legacy. As the owner of Heady Lady Millinery, Ann curated a dazzling personal collection of more than 500 hats, each with its own story. Her designs were worn by presidents, first ladies, and fashion enthusiasts across the country, reflecting her flair for elegance and her belief that a hat was never just an accessory—it was a statement.

Crowned Mrs. Cleveland in 1967, Ann became a beloved public figure, traveling nationally to present her lively hat shows in Cleveland, Palm Beach, and Boca Raton. These events blended fashion, storytelling, and philanthropy, raising funds for causes close to her heart, including the American Red Cross and the Christ Child Society.

Our temporary exhibit celebrates Ann’s extraordinary eye for style, her decades-long influence on Cleveland’s fashion community, and the joy she brought to audiences through her unforgettable hats. Each piece on display honors her creativity, generosity, and the vibrant spirit that made her a true original.

Stop in and see what’s new at the Osborn Learning Center!

If you haven’t stopped by the Bay Village Historical Society in some time, now is the time to visit! After restabilizing the Osborn Learning Center over the winter of 2026, we’re excited to announce a new series of rotating exhibitions. This year, to celebrate our 250th anniversary as a nation, we’ve traced the history of Bay Village and Dover back to the Revolutionary War and beyond. At the new and improved Osborn Learning Center, you can meet several Revolutionary Soldiers who came to call Dover home and later Bay Village home. You can also explore Bay Village’s indigenous past through local archaeological finds and the many histories of indigenous peoples who lived in our area before European settlement. There’s always something new to see and learn about at the Osborn Learning Center, so if you’re a first-time visitor or a frequent flyer, stop by to see what’s new and happening at the Bay Village Historical Society.

2023 “Beadwork: The Beauty of Small Things”
Beadwork was the focus expressed through clothing and accessories. The library featured a
display of purses, small accessories, and various beaded items. A description can be found on
the blog: https://www.bayhistorical.com/clothing-featuring-ornamental-beadwork-at-rose-hill-
museum/
The League of Women Voters, celebrating its 75 th anniversary, was featured in the second-floor
alcove. The League first met at Rose Hill when it was a library.

2022 “A Nod To The Past” highlighted organizations and memorable moments in Bay Village.
Displays included early school memorabilia with a nod to the first graduating class at Parkside
School in 1927 and featured an early graduation dress. 1920s clothing and a poster from the
suffragette movement were focused in the Victorian Parlor. The primary display
commemorated Dover-by-the-Lake Library, the first library in Bay Village, that began at Rose
Hill in 1921. The display highlighted the last 100 years up to the opening of our new library in
the spring. A nod to the military was evident in the library with military memorabilia from WWI
and earlier.
The second floor featured two displays: one of Bay Crafters which was originally on the lower
level of Rose Hill (now BayArts), and the Lake Erie Junior Museum. The museum, which was
housed in what is now the children’s bedroom and bathroom, would become the Lake Erie
Nature and Science Center.
The last display was in the lower area where guests viewed early bathing suits from the 1910s
and 1920s along with vintage postcards.