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The Best 1920s Era Entertainers for Hire in Winchester, KY

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69 1920s Era Entertainers serving Winchester, KY
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1920s Era Entertainment Pricing

Pricing

Using data from quotes sent through GigSalad, we’ve gathered average pricing for hiring 1920s Era Entertainment in your region.

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What Winchester Users Say

5-star review

“Awesome Wedding Music!” – Kate E., reviewing Cincinnati 1920s Era Entertainer Different Hats Promotion Performance. More reviews

Background Jazz Band - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio Featured vendor banner
Background Jazz Band - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio

Background Jazz Band

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5.0 (6)
  • Map pin icon Cincinnati, OH
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester
  • Check mark icon 19 Verified Bookings

Jordan D. said “The band arrived on time. They were extremely pleasant. They were dressed appropriately. Their sound was amazing. They were a joy to have. Would 100%…”

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The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio Featured vendor banner
The Gatsby Gang Jazz Band - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio

The Gatsby Gang Jazz Band

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5.0 (3)
  • Map pin icon Cincinnati, OH
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester
  • Check mark icon 8 Verified Bookings

Karin J. said “Couldn’t be happier with these musicians! If you are looking for a traditional jazz trio feel like we were, don’t look any further. This is your group!!…”

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Matt Snow, "The Cincinnati Sinatra" - Frank Sinatra Impersonator / 1920s Era Entertainment in Cincinnati, Ohio Featured vendor banner
Matt Snow, "The Cincinnati Sinatra" - Frank Sinatra Impersonator / 1920s Era Entertainment in Cincinnati, Ohio

Matt Snow, "The Cincinnati Sinatra"

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5 (111)
  • Map pin icon Cincinnati, OH
  • Vendor category icon Frank Sinatra Impersonator / 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester

Paul R. said “What a great present for my Mother in Law. Matt was a true professional in every aspect in singing many Frankie songs and paying great attention to every…”

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Matt Tolentino - 1920s Era Entertainment in Cincinnati, Ohio

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Matt Tolentino - 1920s Era Entertainment in Cincinnati, Ohio

Matt Tolentino

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5.0 (10)
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  • Map pin icon Cincinnati, OH
  • Vendor category icon 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester
  • Check mark icon 16 Verified Bookings

Courtney W. said “Great group. Out guests loved the music. Very entertaining. I would definitely recomend booking for any event.”

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Different Hats Promotion Performance - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio
Different Hats Promotion Performance - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio

Different Hats Promotion Performance

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4.98 (11)
  • Map pin icon Cincinnati, OH
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester
  • Check mark icon 6 Verified Bookings

Ali C. said “Different Hats did an amazing job at our wedding reception. Between their live performances and DJ services, they really set the tone for the event and…”

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Wedding Jazz Inc - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio
Wedding Jazz Inc - Jazz Band / 1920s Era Entertainment in Cincinnati, Ohio

Wedding Jazz Inc

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0 (0)
  • Map pin icon Cincinnati, OH
  • Vendor category icon Jazz Band / 1920s Era Entertainment
  • Travel distance icon 79 miles from Winchester

Wedding Jazz Inc performs live jazz for your wedding or special event! We perform all the jazz standards by artists such as Miles Davis, Frank Sinatra, and more.

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The Tom Daugherty Orchestra - Big Band / 1920s Era Entertainment in Dayton, Ohio Featured vendor banner
The Tom Daugherty Orchestra - Big Band / 1920s Era Entertainment in Dayton, Ohio

The Tom Daugherty Orchestra

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0 (0)
  • Map pin icon Dayton, OH
  • Vendor category icon Big Band / 1920s Era Entertainment
  • Travel distance icon 122 miles from Winchester

The Tom Daugherty Orchestra is a Nationally Touring show and dance orchestra featuring an exciting and entertaining "Las Vegas Big Band" show style. The…

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Moonlight, Music and Mystery - Singing Telegram / 1920s Era Entertainment in Knoxville, Tennessee Featured vendor banner
Moonlight, Music and Mystery - Singing Telegram / 1920s Era Entertainment in Knoxville, Tennessee

Moonlight, Music and Mystery

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4.98 (48)
Top Performer badge
  • Map pin icon Knoxville, TN
  • Vendor category icon Singing Telegram / 1920s Era Entertainment
  • Travel distance icon 141 miles from Winchester
  • Check mark icon 77 Verified Bookings

Maria B. said “I would recommend them to everyone! They made my sisters miserable day better and she even gave her first smile in a while after watching their performance!…”

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Cherie Blondell - Burlesque Entertainment / 1920s Era Entertainment in Columbus, Ohio Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Cherie Blondell - Burlesque Entertainment / 1920s Era Entertainment in Columbus, Ohio

Cherie Blondell

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4.09 (2)
  • Map pin icon Columbus, OH
  • Vendor category icon Burlesque Entertainment / 1920s Era Entertainment
  • Travel distance icon 150 miles from Winchester
  • Check mark icon 5 Verified Bookings

Tara G. said “I hosted a repeal of prohibition party and Cherie was absolutely perfect. She was kind, professional, engaged with our guests and put on a top notch show.…”

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Quick facts
1920s Era Entertainment in Winchester, KY

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1,247 quotes sent

In the past year, 1920s Era Entertainers have sent 1,247 quotes to event planners

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117th most popular

1920s Era Entertainers rank #117 in popularity out of 545 categories on GigSalad

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5 out of 5 stars

541 1920s Era Entertainer reviews on GigSalad with an average rating of 5 stars

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2.6 days on average to book

From request to booking, it takes 2.6 days (on average) to hire 1920s Era Entertainer

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Kentucky ranks #30

for 1920s Era Entertainer requests in the United States

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1920s Era Entertainment in Winchester, KY


For black-tie affairs, large corporate events, high-class dinner parties, holiday parties, birthday parties, anniversary parties, supper clubs, or other occasions, bands playing 1920s Musical Entertainment and period music from the roaring twenties can be an excellent entertainment choice. Popular entertainers from this fun-filled decade include Josephine Baker, Al Jolson, George Gershwin, Vaudeville Performers and Harlem Jazz musicians (to name a few). Related searches include Big Bands, Swing Bands, Jazz Bands, Jazz Singers. Start your search by selecting your city above.

Some things to consider when hiring 1920s entertainment is to make sure you listen to audio and watch video clips of the performer/group. This will ensure that you truly do book the best for your next event! Next, you want to get references. Talk to people in the area about the performer and get feedback. Finally, get a contract. Many professional performers require a deposit to secure them at your next event. Make sure to read through the contract carefully before contracting their services for your party. Search for 1920s Era Entertainment in Winchester, Kentucky above.

Please note that these 1920s Era Entertainment may also travel to North Middletown, River, Mount Sterling, Judy, Paris, Clay City, Waco, Jeffersonville, Eastern, Sharpsburg, Stanton, Winston, and Moorefield.

Find 1920s Era Entertainment in nearby cities

Richmond Lexington Nicholasville Georgetown Danville Frankfort
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