Come be a cycling guide with WindsorEats!
Come be a cycling guide with WindsorEats!

Love to ride your bike? Love food and drink? Have you been told you have a great personality by someone other than your mother? If so, we’ve got a job for you!

WindsorEats is currently seeking individuals for positions as Cycle Tour Guide & Storyteller for our cycling tours (Bikes & Beers, Wine Trail Ride and Friday Night Lights).

That’s right. We’ll pay you to ride your bike, have fun and make your friends jealous by having the best job ever……ever!

Our guides will be responsible for leading interactive, theme-based cycling tours and events that will provide attendees with enjoyable, engaging, and in-depth experiences of the neighbourhoods and local businesses of Windsor-Essex as well as provide attendees with in-depth knowledge about food and beverage tasting, industries and history.

Knowledge and a passion for food, beer, wine and/or liquor is a must. Experience with beverage and food pairing is a plus as well as knowledge of the industries, history and culture of the region.

Finally, we believe that our guides are the most important element of our tours, so we seek people who are personable, passionate, entertaining, fun and maybe even like to do a song and dance for people, which helps ensure that WindsorEats’ guests have the time of their lives on our tours.

Candidates must:

  • Have a positive ‘can-do’ attitude, sense of humour, and a friendly and outgoing personality.
  • Must have comprehensive knowledge of road and cycling safety, rules and regulations.
  • Must be a capable bike mechanic.
  • Must be a capable of cycling 30+ kilometres at a good pace is needed.
  • Must be knowledgeable about safe riding in both an urban and rural environment.
  • Must be engaging and converse with participants to ensure that they are having the best possible experience.
  • Demonstrate knowledge in one or more of food, beer, wine, or liquor; and one or more of the following: Tour guide experience, acting experience, public speaking experience, food industry expertise.
  • Have experience in interacting with diverse groups of people from a wide range of cultural, racial, and socio-economic backgrounds.
  • Be knowledgeable of and enthusiastic about the history, cultures, and industries of the Windsor-Essex area.
  • Be comfortable with speaking in front of groups of people in a professional manner.
  • Perform well under pressure and demonstrate good judgment and communication skills.
  • Be able to commit to giving at least two tours per month.
  • Exude awesomeness.

We’ll give bonus points to candidates who:

  • Are certified in CPR and First Aid.
  • Have special food or beverage related certifications (Sommelier, Cicerone, etc.)
  • Demonstrate verbal fluency in a language other than English (Preference will be given to French).

Please send your cover letter and resume to

Responsibilities Include:

  • We encourage the guide to bring a cell phone for emergency use.
  • Greet guests as they arrive for tours and socialize with them individually throughout the tour.
  • Provide support to the group. Throughout the ride the Guide should make his/her way up and down the trail of riders to ensure that participants are safe.
  • Be responsible for leading the group to each destination and ensuring their safety along the way.
  • Troubleshoot any issues or problems that may arise i.e. flat tires, broken chains, etc.
  • Provide a general check to ensure bikes are in good condition (i.e. tire pressure) as participants arrive.
  • Prior to each ride the Cycling Guide must go through safety tips, cycling signals and what to do in case in need of help.
  • Review hand signals with participants.
  • Inform participants to the rules of the road that must be adhered to.