Discover 386 professional 1950s era musicians and bands available for hire in Windsor, England, United Kingdom. These vintage performers have received 1,084 reviews from real clients, maintaining an average rating of 5 out of 5.
Of the 386 suppliers listed here, 62 are based within 30 miles of Windsor. The other 324 are willing to travel there.
Also covers suppliers based in London, Guildford, Welwyn Garden City, Aldershot, Brentford, Caterham, Chalfont St Giles, Chertsey and 13 other places within 30 miles.
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Book from £360 (GBP)
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Rates for 1950s era musicians in Windsor currently range from about £100 to £1,300+, depending on group size, performance duration, and specific requirements. Most bookings average around £390, representing excellent value for professional vintage entertainment. Contact the supplier you like for an accurate quote.
Based on 79 enquiries for 1950s Era Musicians & Bands at events in and around Windsor, made through this site in the last two years. Updated 26 October 2026.
Tom Neill (Solo/Duo/Bands)
"Tom is a highly talented musician as well as being very professional when communicating and engaging with clients. We recently asked Tom to perform at an event in Cookham. The band were excellent, the client was delighted - wouldn't hesitate in recommending."
Anna Nightingale Vintage Jazz swing Singer
"Stephanie M
August 2022
5 out of 5
I booked Anna as a solo act for my Parents 50th wedding anniversary. From the moment I enquired online, Anna's communication was flawless. She made me feel very confident in all aspects, including but certainly not limited to song requests and act requirements.
Anna was kind enough to bring a card for my parents and she was respectful and mindful when I told her a few days prior to the event that a family member had passed away. Anna went out of her way to pay tribute on the night and even allowed my father to do the same. I couldn't recommend her enough - truly a great artist and even greater person.
regards
Stephanie"
Tim Payne
"Tim played at my 60th birthday party and was absolutely fantastic. He started with a brilliant acoustic set and then moved into more guitar-driven music as the evening went on. He’s a great singer, really got the party going, and is also a genuinely nice guy. I’d highly recommend him for any party or event."
Elvis tribute and rock n roll show
"Paul was a joy to deal with, he responded to quickly to any messages. Arrived early to set up and had the crowd singing and dancing all night with his sets.
Having the rock n roll show first was a great warm up to his Elvis set which we would happily book again"
Harmonica Lewinsky & The Highway Patrol
"Last night I met up with some pals down at the very hospitable Mermaid Inn to check out the latest musical venture of the great Harmonica Lewinsky.
We’ve always been highly entertained by his music hall/cockney act and indeed his 60s/70s cover material, but this was to be something of a completely different flavour – a country/ western swing experience!
Launching into ‘Glendale Train’, Lewinsky and his band, The Highway Patrol, soon had the place rocking. The sound of finger pickin’ Dzal Martin’s Telecaster was the perfect accompaniment and upright bass player Ewan Penkey’s rhythm proved that no drummer was required.
As well as rockers such as ‘Panama Red’, ‘Folsom Prison Blues’ and the brilliant tongue-twisting ‘Hot Rod Lincoln’, Lewinsky and the boys were also able to deliver truly 'hurtin' & heartbreaking' melancholy classics such as Warren Zevon’s ‘Carmelita’ and Kenny Rogers’ ‘Ruby’.
Their touching version of Commander Cody’s ‘Seeds & Stems Blues’, featuring the wonderful pedal-steel guitar playing of John Davis, (who had been impeccable all evening) had me almost crying into my pretzels.
Personality and humour has always been an important part of Harmonica Lewinsky’s act and, with his usual banter and rapport, he certainly didn’t let us down. We particularly enjoyed the tongue-in cheek ‘All My Exes Live in Texas’.
Thanks for a great night, boys – we look forward to the next time."
Lorraine And The Flames
"Lorraine and the Flames are hands down one of the best groups I've heard in a long time. We were hosting an outdoor Jazz and BBQ evening and the guys couldn't have been more amazing! The music was perfect and Lorraine's voice is sublime. They set the atmosphere and mood from the moment they started, and so many of our guests commented on how wonderful they were. Thank you so much, Lorraine and the Flames for a perfect evening. We look forward to working with you all again in the future. Freya"