The Crossing Trek 2021 is VIRTUAL

Create your own route and walk the walk to raise funds and awareness for homeless services in Waterloo Region

Thanks to everyone who participated in The Crossing Trek - Virtual 2021! We raised over $15000 for homeless services.

Check back in November 2021 for the Feb 2022 event registration details.


Trekking and Covid-19

This trek has always been about community, but this year things will look a little different. If you are walking with others, please limit it to small group. As a participant in The Crossing Trek you must follow the government's Covid-19 safety guidelines. Carry a mask at all times, so you have it on hand should you need to enter a store, restaurant, washroom facility, etc, or if you are unable to maintain a 6ft distance from others.


This is not a race, it's a journey. Since there are no rankings or competition, we allow help and support from family and friends. You MUST arrange a support contact person prior to embarking on your trek.


Due to Covid-19, we encourage you to arrange support with someone from your bubble who can get you to/from your route start and end points, and be on-call throughout your trek to bring you additional food, gear, etc. 


This year, since many of us will be taking different routes, we encourage you to use a tracking app of your preference to keep track of your route and distance. After the event, you'll be able to share your route map via social media!

Please note that tracking may drain your cell phone battery faster (as will cold temperatures), so consider bringing a portable phone charger power bank. 


This is a fundraising event, with all proceeds going towards The Working Centre, an amazing multi-faceted organization that improves the quality of life for so many people in Waterloo Region. 

Set up your fundraising page through Race Roster when you register for the trek! 





“Would like to express my appreciation to you and your Trek Crew for pulling off this amazing event. Clearly there was a mountain of detail to process from commemorative buttons to all the paperwork and everything in between. Allow me to congratulate you and your team for excellent planning and exceptional execution. It demonstrates again what can be done by a group of committed people finding the compassion to address societal needs and actualizing a plan.  It sends out inspirational ripples to the larger community. These events bring out the best in all of us.”

- Rolf and Helga Thiessen, Optimist Trekkers (completed the 24 km with a sense of joy and accomplishment and humbled by those who completed the full trek)

“The trek is one of the most challenging, fun, and rewarding experiences I have ever had in my life. You and your team were amazing and it was something I don't think any of us will ever forget!”

- Michael McCarville, Full Trekker


“thank you and your team for the fantastic leadership , vision and fortitude in bringing community together”

- Helga Thiessen, Optimist Trekker

“Thanks for your vision and determined leadership allowing us to join you in raising awareness and funds for a great cause. It even got me out hiking regularly this winter, which was another goal of mine.”

- Taylor Martin, Pioneer Trekker


“I loved the enthusiasm, the wanting and willingness of everyone to help with this cause... I loved the fact that other people felt so supported while trekking, as I did.”

- Ron Cherry, Full Trekker


“As a participant and member of our community I would like to thank you for the fine event you organised and for the thoughtfulness of you and so many of the supporters.  I am sure this will give a boost to the Working Centre. The trek was well organised with good attention to safety. I also thought that you did a good job in choosing the weather; cold enough to be cognisant of the plight of the homeless but not too cold for we wimps who are used to spending our time in warm houses”

- Joy Geiger, Pioneer Trekker

“It was an awesome trek. You can count me in if you need volunteers for next year.”

- Full Trekker


“Congratulations Tessa and crew. What an incredibly successful community event. Thx for all the good energy. See you next year!”

- Trekker

“What a community achievement! By word of mouth, press, tv and social media your event acknowledges the raised donations and the support provided to the Working Centre. Through media and personal correspondence it will draw people to your next event. The three of you have done well and I am happy to have you as part of my circle as friends and community leaders. Accept all accolades as you deserve recognition.


The pace, coordination, information, safety, check-points, checkpoint support services, sponsors, coffee, snacks, beverages and much more were essential comforts to all who walked in sub-zero temperatures. The gear listing provided great guidance and the actual gear checking made people realise that walking in winter is no small feat.


I achieved a personal best yesterday by walking to Kiwanis Park an estimated distance of 40 km. I had made lots of contact with many people. Many of those people are new members of GVTA. How can we ever thank you for supporting our association?


…and to my surprise, I was notified this morning via a text message that an old classmate of mine, Ian Decesare has made a fine contribution to the Working Centre. The donation is made from Malta. I can now claim that you event has gone international. With much love to all of you for this unprecedented event.”

- Charles Whitlock, Director of the Grand Valley Trails Association and Optimist+ Trekker


Meet The 

Trek Director

Tessa Jennison is a four-time Adventure Racing World Series athlete, one of Canada's few female adventure event directors, and participated as TAC in "World's Toughest Race: Eco-Challenge Fiji". Her love of her community spurred an interest in developing an engaging event that combines adventure endurance with philanthropy, and stirs the spirit to challenge oneself in a multitude of ways. As a graduate of University of Waterloo's School of Urban and Regional Planning, Tessa has created an event that explores our collective potential to have a positive impact on our community and on each other.