In addition to her solo career, Winslow has been a member of four bands, including a duo with Nick Katzman and Nite Train.
While she had been teaching a full load of school and private students for over a decade,[1] her primary notability has been from touring in the eastern United States and Europe with Katzman, starting in 2006.
[7][8] As part of her family's group, The Winslows, she toured throughout the folk music festival circuit, including The Great Hudson River Revival.
[1][9][10] In December 2021, she received the degree of Doctor of Ministry, honoris causa, from Covenant of Avalon Theological Seminary.
She also played in the 1990s in concerts with Two Story Tuesday and Bojembe around upstate New York, including Glens Falls, Albany, and Colonie.
[23] This included a performance at Marietta, Ohio's River City Blues Festival in March 2009,[23][24] a show in Easton, New York, blues festivals in Denmark and Germany, and return shows at Caffe Lena and the Good Coffeehouse with Nick Katzman.
[29] Bojembe's most recent public gig was at the River Street Beat Shop in Troy, New York, for which a blogger wrote that "Winslow's roots are in the deep folk-blues tradition, (while) her work with Bojembe leans toward a decidedly funky groove with a world music spin.
As related in that article, Katzman has mentored a number of younger blues artists, including Winslow, taking her "under his wing."
In April 2006, Katzman was slated to perform at the Good Coffeehouse Music Parlor in Brooklyn, his favored venue in "the States".
[42] Instead, Winslow substituted for Green; in Katzman's own words: I was getting my e-mail and was about to zap what I thought was ... spam....
I decided to open it anyway and it turned out to be a letter from a singer/guitarist named Thomasina Winslow who said she was covering tunes from my Kicking Mule LPs on her new CD.
She said that I was a primary musical influence for her, so I've asked her to come and do a guest appearance at the gig, and she said she'd come all the way down from Albany to do it, so it looks like we'll be hosting Thomasina Winslow on that night, too.
[44] The duo played at the Stamford Arts Centre Blues and Folk Festival, and were the second-billed act for "Guitar Day" ("8.30pm Nick Katzman & Thomasina Winslow 10.00pm Jeff Lang").
"[47] Blogger Ginger Mayerson called their performances "cute" and "Oh, I just love these trips down memory lane, don't you?
They performed in Bad Sobernheim and Skarrild, Denmark at the Danish Folk, Blues, and Ragtime Guitar Festival.
Winslow recorded a music video with Marco Haber of Mudfunk in December 2007, covering "Fly Like An Eagle".
[54] She appeared as a part of a group of female musicians at a Caffe Lena show called Ladies Sing the Blues in February 2010.
[1][2] Schenectady County Community College, of which she was an alumna, has set up a scholarship fund in her name, with the first fundraising concert on August 9, 2024.