Due to the ongoing situation with Covid-19, the 2020 Downtown Milton Street Festival has been cancelled.

Please look for applications for the 2021 festival in December 2020.

We are looking for a wide selection of engaging, lively, and talented performers to participate in the Downtown Milton Street Festival (DMSF) on Saturday, June 6, 2020.  Performance commitments are typically 60 minutes in length (includes transition, turnover, performance, etc) and will take place on stages and performance areas located in Downtown Milton.

Event Overview

The Downtown Milton Street Festival is a family focused event that offers attractions and activities for a wide range of ages! This event showcases over 130 vendors, with returning vendors giving a 94% satisfaction rating to this event.  

Festival Goals and Objectives

  • To bring the community together
  • To provide a fun and safe family-oriented event
  • To showcase Downtown Milton
  • To showcase local talent
  • To showcase all vendors
  • To provide increased opportunities for businesses
  • To provide a diverse, inclusive and unique event experience

Target Audience

Families and people of all ages from Milton and surrounding communities

Expected Attendance: 90,000 people

By completing this application, all entertainers agree and consent to the following conditions:

  1. All performances must be suitable for a general family audience rating.  
  2. Appropriate clothing must be worn at all times.
  3. Performances may not include any high risk or unsafe elements that may put the public or the performers at risk. (eg. use of knifes, fire and other dangerous elements are not permitted).
  4. The comfort or safety of others must never be jeopardized.
  5. Drunken or lewd behaviour will not be tolerated.
  6. All entertainers must provide proof of $2 million liability insurance. The certificate of insurance must name the Corporation of the Town of Milton (mailing address: 150 Mary Street, Milton, ON L9T 6Z5) as an additional insured. If required, you may purchase insurance through the Town of Milton instead for a fee of $50.00.
  7. Payment details will be confirmed if your application is approved.
  8. Please note that DMSF has received sponsorship from a number of our partners and as such, entertainers may not seek out their own sponsorship regarding their performances.

If any of the above conditions are not met, entertainers will not receive payment.

You must apply online to be considered as an entertainer.  Please note that there are no restrictions based on past performances with DMSF.  New and returning entertainers will be considered equally.


The application deadline is FRIDAY, MARCH 6, 2020 at 5:00 p.m. ONLY selected performers will be notified via phone and/or email on or before FRIDAY, MARCH 27, 2020.

Online Entertainer Application Form

    All fields with * are required


    Cheque can be payable to the name and address provided above.Cheque to be payable to:

    WSIB InsuredLetter of Exemption received from WSIBNeither
    I have my own general liability insurance of $2 million (Please Provide Proof)I intend to purchase insurance for a cost of $50.00 through the Town of Milton (Due by 13 April 2020 upon approval)

    Thank you for your interest. ONLY selected performers will be notified via phone and/or email on or before FRIDAY, MARCH 27, 2020.

    Phone: 905-876-2773
    Email: events@downtownmilton.com
    Mailing Address:
    Downtown Milton BIA – 251 Main Street East, Suite 103, Milton, ON L9T 1P1