December 8, 2021

Old Town Live – The Dukes

Jim grew up in the Boston area where he hosted an oldies radio show and started singing with a local doo wop group. He is an avid record collector, and has been in the entertain…

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December 10, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 10, 2021

Old Town Live – Eklectik Haze

The hottest new thing to hit the streets of Central Florida, Eklectik Haze is a youthful, high energy band that will get you on your feet!

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December 11, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 11, 2021

Holiday Golf Cart Street Parade

Join us right before our weekly Car Cruise as residents from Sherwood Forest RV Resort present their personal golf carts in all of their Holiday glory!   Golf carts will begin arriving at 6…

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December 11, 2021

Old Town Live – Saloonatix

Saloonatix originated in 2007 in the Central Florida area. They are a Five Piece Band consisting of Acoustic, Rhythm Guitar, Lead Guitar, Bass Guitar, Drums and Keyboards playing Southern Rock, Cur…

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December 12, 2021

Old Town Live – Will Yancy

From Elvis to George Jones to Buddy Holly, Will's smooth vocals move across the most favored musical genres to insure an unforgettable experience for all. Will spends a great deal of time traveling…

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December 12, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 15, 2021

Old Town Live – Karen Kallin

Go back in time with Karen as she sings all of your favorite Doo-Wop songs of the past!

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December 17, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 17, 2021

Old Town Live – Groove Infusion

Groove Infusion is a band made up of musicians that have one goal in mind....to make you dance!

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December 18, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 18, 2021

Old Town Live – Rocktown

Rocktown is Orlando Florida’s #1 party rock cover band. Members of Rocktown have shared the stage with many national acts including Joan Jett and the Blackhearts, Foreigner, Cindy Lauper, Puddle …

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December 19, 2021

Old Town Live – Cowboy

Sing along with Cowboy as he sings all of your favorite country hits from then and now!

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December 19, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

Read more.

December 22, 2021

Old Town Live – The Dukes

Jim grew up in the Boston area where he hosted an oldies radio show and started singing with a local doo wop group. He is an avid record collector, and has been in the entertain…

Read more.

December 24, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 24, 2021

Old Town Live – Sheila & The Sound

Sheila and The Sound is a unique cover band from Orlando, Florida playing 6 different genres of music from 6 different decades!  Dance or sing along as they perform for everyone at Old Town!

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December 25, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

Read more.

December 26, 2021

Exotic Cars & Coffee

Join us for some coffee and car talk.  The term "exotic" is used in marketing by automakers to mean "unusual or expensive," but we like to think it means "the type of vehicle that dreams are made of.…

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December 26, 2021

Import Car Show

Join us on the last Sunday of every month from 4:00pm – 9:00pm on Trophy Row for our Import Car Show. **All cars must be SHOW QUALITY and will enter off of Holiday Trail and park on Trophy Row st…

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December 26, 2021

Holidays at Old Town

Bring the entire family and watch as the holidays come alive at Old Town. This truly unforgettable event will bring back old memories and create new ones as you enjoy a classic all-American holiday ex…

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December 29, 2021

Old Town Live – Bill D. Williams

Bill D. Williams, Black Country, singing classic country, modern country, oldies, and much more.

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December 31, 2021

New Year’s Eve Celebration

End 2021 with a bang at a New Year’s Eve Celebration presented by Old Town and Fun Spot. Bring the family for a car show, live entertainment, and a free concert featuring The Rock Show. Old To…

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December 31, 2021

Old Town Live – The Rock Show

The Rock Show is a modern rockumentary based on legendary music and bands from the late 60s, 70s, and 80s, including songs from The Beatles, Led Zeppelin, Queen, Pat Benatar, Pink Floyd, Heart, Journ…

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January 1, 2022

Old Town Live – Rocktown

Rocktown is Orlando Florida’s #1 party rock cover band. Members of Rocktown have shared the stage with many national acts including Joan Jett and the Blackhearts, Foreigner, Cindy Lauper, Puddle …

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January 2, 2022

Latin Fest

Join Southern Breeze on the first Sunday of every month as they host Latin Fest at the Old Town Stage. Únase a Southern Breeze el primer domingo de cada mes, ya que organizan la Fest Latina en el …

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January 5, 2022

Old Town Live – The Dukes

Jim grew up in the Boston area where he hosted an oldies radio show and started singing with a local doo wop group. He is an avid record collector, and has been in the entertain…

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January 7, 2022

Old Town Live – Switch

SWITCH Back to the Eighties : 80's Tribute band covering all the hits that made the 80's great.

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January 8, 2022

Old Town AutoFest – Judging Car Show

Join us for Old Town AutoFest - a judged car show - featuring Muscle and Classic Cars.  Participating cars must be show quality 1964 and newer muscle and high performance cars and trucks and 1983 and…

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January 8, 2022

Old Town Live – Fast 4Ward

Fast 4 Ward is a five member country band, with a rock edge. Their cover songs consist of the latest and most popular country music heard on today's radio, along with some older traditional songs. Mus…

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January 9, 2022

Three Kings Day

The Feast of the Three Kings is an intricate part of Latin Folklore. Traditionally, it is on this day that children receive gifts from the Three Kings. This year the Kissimmee/Osceola County Chamber's…

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January 9, 2022

Old Town Live – Will Yancy

From Elvis to George Jones to Buddy Holly, Will's smooth vocals move across the most favored musical genres to insure an unforgettable experience for all. Will spends a great deal of time traveling…

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January 12, 2022

Old Town Live – Karen Kallin

Go back in time with Karen as she sings all of your favorite Doo-Wop songs of the past!

Read more.

January 14, 2022

Old Town Live – Occasional Astronauts

Occasional Astronauts is a premier Central Florida-based band specializing in performing your favorite Rock, Country, and Pop hits from the 60's to today.

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January 15, 2022

Old Town Live – MPiRE

With a polished sound and assorted mix of FIVE never-to-forget vocalists, MPiRE satisfies any and all musical appetites. Performing a broad repertoire of great songs from all genres, MPiRE delivers th…

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January 16, 2022

Old Town Live – Southbound Trio

Southbound is a top shelf country/party band from Orlando Florida, featuring an amazing line up of some of the area’s best, world-class singers and musicians! Southbound is one of Central Florida’…

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January 21, 2022

Old Town Live – Blue Stone Circle

Blue Stone Circle will leave you dancing in the streets! With their hot sound and unmatched energy, every audience will be asking for more.

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January 22, 2022

Old Town Live – Johnny Wild & The Delights

Johnny Wild and The Delights - the Southeast's number one '50s and '60s band, are your true time machine back to the style and sound of the Golden Age of Music. From the early days of Rock ’n Roll …

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January 23, 2022

Exotic Cars & Coffee

Join us for some coffee and car talk.  The term "exotic" is used in marketing by automakers to mean "unusual or expensive," but we like to think it means "the type of vehicle that dreams are made of.…

Read more.

January 23, 2022

Old Town Live – Cowboy

Sing along with Cowboy as he sings all of your favorite country hits from then and now!

Read more.

January 26, 2022

Old Town Live – The Dukes

Jim grew up in the Boston area where he hosted an oldies radio show and started singing with a local doo wop group. He is an avid record collector, and has been in the entertain…

Read more.

January 28, 2022

Old Town Live – Greg Warren Band

The Greg Warren Band is a young high energy modern country band based out of Orlando Florida. Formed in 2011, their very first show was headlining the House of Blues in Orlando with support from Jared…

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January 29, 2022

Old Town Live – Liverpool Live

Consistently voted #1 Beatles show by fans, Liverpool Live takes you through all the years of the Beatles. These guys are true entertainers. They will have you singing and clapping to all of the hits.…

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January 30, 2022

Import Car Show

Join us on the last Sunday of every month from 4:00pm – 9:00pm on Trophy Row for our Import Car Show. **All cars must be SHOW QUALITY and will enter off of Holiday Trail and park on Trophy Row st…

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February 6, 2022

Latin Fest

Join Southern Breeze on the first Sunday of every month as they host Latin Fest at the Old Town Stage. Únase a Southern Breeze el primer domingo de cada mes, ya que organizan la Fest Latina en el …

Read more.

February 27, 2022

Exotic Cars & Coffee

Join us for some coffee and car talk.  The term "exotic" is used in marketing by automakers to mean "unusual or expensive," but we like to think it means "the type of vehicle that dreams are made of.…

Read more.

February 27, 2022

Import Car Show

Join us on the last Sunday of every month from 4:00pm – 9:00pm on Trophy Row for our Import Car Show. **All cars must be SHOW QUALITY and will enter off of Holiday Trail and park on Trophy Row st…

Read more.

March 19, 2022

32nd Anniversary Classic Car Show/Cruise

Old Town celebrates the 32nd Anniversary of the Saturday Nite Classic Car Show/Cruise. It’s been 32 years since Old Town invited classic cars to drive down the brick-paved main street and the beg…

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March 27, 2022

Exotic Cars & Coffee

Join us for some coffee and car talk.  The term "exotic" is used in marketing by automakers to mean "unusual or expensive," but we like to think it means "the type of vehicle that dreams are made of.…

Read more.

March 27, 2022

Import Car Show

Join us on the last Sunday of every month from 4:00pm – 9:00pm on Trophy Row for our Import Car Show. **All cars must be SHOW QUALITY and will enter off of Holiday Trail and park on Trophy Row st…

Read more.

May 7, 2022

Old Town Live – The Hooligans

British rock from the 60s - 90s. Orlando's top musicians play The Beatles and The Stones to Oasis, The Clash and The Cure.

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July 29, 2022

Old Town Live – Eklectik Haze

The hottest new thing to hit the streets of Central Florida, Eklectik Haze is a youthful, high energy band that will get you on your feet!

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December 9, 2022

Old Town Live – Eklectik Haze

The hottest new thing to hit the streets of Central Florida, Eklectik Haze is a youthful, high energy band that will get you on your feet!

Read more.