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105 1920s Era Entertainers serving Portland, OR

Featured

The Apollo Trio

4.98 (68)
Top Performer
95 Verified bookings

  • Portland, OR
  • Jazz Band / 1920s Era Entertainment
  • $2000 and up

Tess D. said “The Apollo Trio was absolutely amazing at our wedding! They brought incredible energy and truly made the evening unforgettable. So many guests said it was the best wedding band they’ve ever heard.... ”
Featured

Me'lanie Talent

5.0 (10)
Top Performer
13 Verified bookings

  • Beaverton, OR
  • Corporate Entertainment / 1920s Era Entertainment
  • 6 miles from Portland
  • $200 & up

Heather C. said “This was a great experience and appreciate the clear communication and professionalism. Will definitely book again in the future =) ”
Featured

Elizabeth Wisler, Music Around the World

5.0 (32)
57 Verified bookings

  • Beaverton, OR
  • Accordion Player / 1920s Era Entertainment
  • 6 miles from Portland
  • $125 to $600

Anna L. said “Terrific with communication, Elizabeth arrived on time, seamlessly set up and played continuously for Dad's 90th birthday party. We had a much larger crowd than expected, and she monitored the... ”

UpFront Band

4.96 (43)
Top Performer
45 Verified bookings

  • Vancouver, WA
  • Jazz Band / 1920s Era Entertainment
  • 8 miles from Portland
  • Two hrs: duo=$450 up to 6-piece=$1400 (varies)

Dana D. said “We recently hosted a party and we had the pleasure to listen to Upfront 2 band members and they were amazing. We will definitely book them again and hopefully the whole band. I definitely recommend... ”

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

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Quick facts for 1920s Era Entertainment in Portland, OR

904 quotes sent

In the past year, 1920s Era Entertainment have sent 904 quotes to event planners.

153rd most popular

1920s Era Entertainment rank #153 in popularity out of 539 categories on GigSalad.

5 out of 5 stars

There are 805 1920s Era Entertainment reviews on GigSalad with an average rating of 5 stars.

1.2 days on average to book

From request to booking, it takes 1.2 days (on average) to hire a 1920s Era Entertainment.

Popular events

1920s Era Entertainment are typically hired for Retirement Community Events in Portland, OR.

Oregon ranks #19

Oregon is the 19th most popular state for 1920s Era Entertainment requests in the United States.

Past events for 1920s Era Entertainment in Portland, OR

Book Them!

1920s Era Entertainment

5.0

January 22, 2026

1.5 hour

We had a Speakeasy Event at our Senior Living Community, and they were an absolute hit! They are able to play so many different types on genres and got our residents out on the dance floor. We will definitely be booking them again for a future event.
Event total

$350

About booking 1920s Era Entertainment in Portland, OR

If you’re planning a wedding, corporate event, or birthday party with a Roaring Twenties or Great Gatsby theme, you’ll need authentic 1920s era entertainment to pull it off. Get your guests doing the Charleston with live music from a jazz band or jazz singer. Or, hire flapper dancers to show them how it’s done. You can also keep the audience in their seats with a captivating vaudeville act or magic show.

The cost of booking 1920s entertainment in Portland, OR will vary depending on the performance length, the type of performer you want, and the complexity of the show. A full show with a 1920s theme complete with multiple jazz musicians and flapper dancers in costume will charge more than a solo performer with a simpler setup. Contact the local 1920s entertainers above to get a quote customized for your event.

While browsing Portland 1920s era entertainment, look through profiles to see photos and watch videos of their performances. Then read reviews from past clients to see if they have experience with events like yours and what it will be like to work with them. When talking with performers, discuss important details like setup requirements, event schedule, and any special requests for costumes, props, or songs.

Once you find the band or performer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to hire 1920s entertainment. You can talk with performers, confirm the details of the agreement, and make a secure payment all in one place. Every GigSalad booking is protected by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and enjoy the show!

1920s Era Entertainment serving the Portland, OR area

These 1920s Era Entertainment serve the wider Portland and Multnomah county area and travel to West Haven-Sylvan, Raleigh Hills, Milwaukie, West Slope, Beaverton, Oak Grove, Cedar Hills, Lake Oswego, Oatfield, Happy Valley, Tigard, Marylhurst, McLoughlin, Vancouver, West Linn, Clackamas, Gladstone, Aloha, King City, Tualatin, Hazel Dell, Gresham, Fairview, Damascus, Oregon City, Hillsboro, Sherwood, Troutdale, Salmon Creek, and Camas.