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On Park Entertainment


We've been providing family entertainment for over 50 years, so we know what works. With a diverse programme of entertainments and activities on offer every day and night throughout the holiday season, we ensure that there is something for all the family to enjoy.

Following the latest Government announcements, we’ve reviewed what you’ll be able to use and do in our parks – and are excited to announce that this now includes some indoor and outdoor activities.



Entertainment at Waterside

Waterside Peak Season Entertainment Schedule

You’ll have plenty of fun at Waterside! From live music at The Shack to family outdoor games, kid's discos, and more!

Download our FREE Waterside Holiday Group app here


Book a Boomer Visit

Book a Boomer visit to your accommodation. 

Boomer can't wait to meet everyone and this year he'll even pop over to your accommodation to say hello! 

To book your Boomer visit just email 


Live @ The Venue

We're hoping to bring Live @ The Venue back on Saturday 15th August, subject to government guidelines.  



Friday 18th September - Jump! (Waterside's favourite party band)

Monday 21st September – TBA

Friday 25th September – Vivo (Party band)

Monday 28th September –  TBA

Saturday 3rd October - The New Pacemakers (Former backing band to Gerry Marsden)  

Monday 5th October - Paul Dumas (Comedy)  

Saturday 10th October - Shades Of Midnight (Party band) 

Monday 12th October - Richie Austin (Magic and illusion)  

Saturday 17th October - Freaky Blinders (3-piece party band)  

Friday 23rd October - Larger Than Life (A Boyband tribute) 

Saturday 24th October - The Styles (Party band)  

Sunday 25th October - TBA 

Monday 26th October - TBA 

Tuesday 27th October - TBA 

Wednesday 28th October - El Loco (A night of comedy)  

Thursday 29th October - Halloween Event & Forever Jackson (A tribute to Michael Jackson)  




Friday 30th October - Halloween Event

Saturday 31st October - Halloween Event

Saturday 7th November - Ultra 90s (Top UK 90s act)  

Tuesday 10th November - Ryan Davies (Live & Acoustic in the Sports Bar) 

Saturday 14th November - Danny Foster and The Big Soul Corporation

Tuesday 17th November - Ryan Davies (Live & Acoustic in the Sports Bar) 

Saturday 21st November - Jump (Waterside's favourite party band)  

Tuesday 24th November -Ryan Davies (Live & Acoustic in the Sports Bar) 

Saturday 28th November - Firekind (Award winning rock band) 


Live @ The Shack

Enjoy the atmosphere at our beach bar The Shack or treat yourself some tasty local food on our Southside terrace, whilst listening to our fantastic acoustic musicians

(Weather dependant)


Saturday 8th August– Caz Krelle

Sunday 9th August– Powelly

Friday 14th August – Powelly

Saturday 15th August – Caz Krelle

Sunday 16th August – Perfect Storm

Friday 21st August – Powelly



Saturday 22nd August – Ryan Davies

Sunday 23rd August – Tom Martin

Friday 28th August – Hamish

Saturday 29th August – Milk & Two

Sunday 30th August – Caz Krelle


Entertainment at Chesil Vista

Chesil Vista Peak Season Entertainment Schedule

You’ll have plenty to do during your Chesil Vista stay- with live music at Breeze, family outdoor games, kids’ discos and more!

View our off peak 2021 entertainment schedule to plan your fun filled stay.

Book a Vic Visit

Book a Vic visit to your accommodation. 

Vic the Vista Monster loves to meet you all, so this year she'll be making visits to see everyone in their accommodation. 

To book your Vic visit email 

Live @ The Venue

We're hoping to bring Live @ The Venue back on Saturday 15th August, subject to government guidelines.  


 Saturday 26th September – Vivo (Party Band) 

Tuesday 29th September - TBA 

Friday 2nd October - The New Pacemakers (Former backing band to Gerry Marsden)  

Friday 9th October - Shades Of Midnight (Party Band) 

Sunday 11th October - Richie Austin (Magic and Illusion) 

Friday 16th October - Freaky Blinders (3 piece party band) 

Friday 23rd October - The Styles (Party Band) 

Saturday 24th October - Larger Than Life (A Boyband Tribute) 

Sunday 25th October - TBA 

Monday 26th October - Jimmy Tamley (Ventriloquist)  

Wednesday 28th October - Forever Jackson (A tribute to Michael Jackson) 

Thursday 29th October - Halloween Event & Music from Northern Vibes 



Friday 30th October - Halloween Event

Saturday 31st October - Halloween Event

Monday 2nd November - Ryan Davies 

Saturday 7th November - Reggaelicious (One of the UKs finest reggae bands)

Monday 9th November - Ryan Davies 

Saturday 14th November - The 60s Explosion (Music from the 60s)

Monday 16th November - Ryan Davies 

Saturday 21st November - The Glen Leon Band (The incredible Glen Leon and his band)

Monday 23rd November - Ryan Davies 

Saturday 28th November - Jump! (Chesil's favourite party band)



Live @ Breeze

New for 2020 - Live @ Breeze.  Enjoy varied acoustic sets at the outdoor seating terrace outside Breeze Bar & Grill.

(Weather dependant)


Saturday 1st August – Milk & Two

Saturday 8th August – Perfect Storm

Saturday 15th August – Powelly

Saturday 22nd August – TBA

Saturday 29th August – Powelly


Plus acoustic sets every Thursday at 6pm!


Entertainment at Osmington

Live @ The Country Club Terrace

(Weather dependant)


Saturday 8th August – Tom Martin

Saturday 15th August – Ryan Davies

Saturday 22nd August – A Perfect Storm

Saturday 29th August – Ryan Davies


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