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Sammy P. said “I hired Matt to come in and perform for the cocktail and dinner hours during my reception for roughly 2.5 hours. Being the bride, I unfortunately wasn't…”
Krystal K. said “The Singapore Slingers did a wonderful job at our show! They are very easy to work with and know what they're doing! They came dressed in 20's era wardrobe…”
Hannah C. said “Ron, Lizzie and everyone with them were wonderful to work with! We couldn’t have chosen a better band for our formal event. These guys are the real…”
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The Tom Daugherty Orchestra is a Nationally Touring show and dance orchestra featuring an exciting and entertaining "Las Vegas Big Band" show style. The…
Christine S. said “I booked Razzamatazz & Jazz for our company Christmas party, which was 1920's themed. The band was very punctual and easy to work with. Everyone at…”
Kristie Q. said “Andrew has played at the wine bar for many years, sometimes with other band members and solo. He is very talented and can accommodate any occasion. He…”
Rose G. said “Jazz Revolution was the perfect choice for our celebration. All of the band members were professional and very talented. The lead vocalist was absolutely…”
Offers Virtual Services
Innovative 8-string guitarist Brad Bailey performs Jazz, Pop, and Blues hits from Stevie Wonder to Sinatra and Ed Sheeran to Eric Clapton in a gentle but feel-good…
Adam S. said “This is the second time that I have had Claudia perform in my home. I would not use ANYONE ELSE. Claudia brings more than beautiful music (which make…”
In the past year, 1920s Era Entertainers have sent 2,652 quotes to event planners
1920s Era Entertainers rank #77 in popularity out of 544 categories on GigSalad
477 1920s Era Entertainer reviews on GigSalad with an average rating of 5 stars
Dinner Parties in Winchester
From request to booking, it takes 3.2 days (on average) to hire 1920s Era Entertainer
Find your best flapper dress and bust out a Gatsby-esque fedora hat and get ready to swing! Let these great bands travel you back in time to the roaring twenties. An era full of swingin' music, jazz greats, and trying to get around that pesky Prohibition. So what are you planning? A birthday party, anniversary, or themed event? Let one of these fantastic bands, musicians, or singers set the mood and get your guests a swingin'! So quit sitting there tappin' your toes and get to booking one of these great 1920s Era Entertainment acts today! Search for 1920s Era Entertainment in Winchester, Kentucky above.
Please note that these 1920s Era Entertainment may also travel to North Middletown, Mount Sterling, Mariemont, Waco, Paris, Clay City, Jeffersonville, Judy, Winston, Stanton, Irvine, and Sharpsburg.