42 cycling, running, road, and other events in Milton, Ontario

The date has been set for July 11th, 2026!

We are proud to announce that this event is sanctioned by Athletics Ontario.

We are thrilled to announce that we are partnering with La Sportiva for our events this year. Not only will La Sportiva be at our races with their demo fleet of shoes to try but they will also be giving away 2 pairs of shoes!

We are also now working with a new, LOCAL, nutrition company called THN Labs. They are generously providing each runner with gels in their race kit as well as gels available at our aid stations. The gels contain only 4 ingredients: maple syrup, tahini, sea salt, and rowanberry extract. For more information on the product, click on their logo below:

A TRAIL RACE & AN ADVENTURE

We are very excited to be offering a unique trail race that is unlike any of our other events. Here are a few of the features that makes this race extra cool:

• The 50km event (actually about 51.8km) is a point-to-point race. We will bus participants from the finish line parking lot all the way to the start and then the runners will run the entirety of the Toronto Bruce Trail section. The 50km course will have a 10 hour cut-off. PLEASE NOTE: We consider this an intermediate level course. It is tough but beautiful. Although there aren't any specific qualifications, this is not recommended for runners who have not completed a 50km already (try the 27.5km event - you'll love it!). Trail shoes are necessary.

-The 25km event (actually about 27.5km) is also a point-to-point race that, although shorter, offers an incredible experience along some of the most incredible sections of the Toronto Bruce Trail. The 25km course will have an 8.5 hour cutoff. This is also a difficult course but, due to the 8.5 hour cutoff, it is manageable for runners with some trail running experience. Plan on being out at least 1 hour longer than your typical 25k race.

We will also be offering a 10km OUT-AND-BACK race. Participants will start at Kelso Conservation and run 5km (through Hilton Falls Conservation Area, across Sixth Line, and along the escarpment before turning around and heading back to Kelso Conservation Area. This will be a hilly and challenging 10km course.

• In addition to a sweet finisher's medal, runners who complete the 50km event will also earn a Toronto Bruce Trail Club End-to-End patch. The 2024 medal pictured below (all photos are from Sue Sitki, our Race Photographer)

• The entire course is run on the permanently marked Bruce Trail (all of it is on the white blazed main trail). Although we will have some great aid stations along the way, we will NOT be adding additional flagging to this course (except for the final 5km, which is being flagged for the 10km out-and-back course). Let us repeat that so that you know what you are signing up for- ONLY FINAL 5km OF THE COURSE WILL BE FLAGGED! You are going to get a true Bruce Trail adventure! You simply have to follow the white blazes the entire way. The blue blazes on the Bruce Trail indicate a side trail, which we WILL NOT be using for this event. The Bruce Trail is well marked and easy to follow. The Toronto Section of the Bruce Trail is very well maintained, heavily travelled, and very clearly marked.

-This is going to be a SMALL, grassroots, community event. We will have an absolute maximum of 200 participants total. Once the event is full, we will not be managing a waitlist.

Here is an image that helps to explain how to follow blazes:

Amongst other interesting features, this course will feature the following beautiful sites:

1. Cheltenham Badlands: These unique formations are actually just outside of the Toronto Section but this is where the race will start. These were formed at the base of an ancient sea over 450 million years ago.

2. Terra Cotta Conservation Area: In addition to some awesome trails, this conservation area boasts ponds, streams, and an important wetlands area. You will quickly find yourself in a trail runner's paradise and, since you will still be fresh, you will adore this part of the course.

3. Silver Creek Conservation Area: With over 1000 acres, this area has lush forests, great trails, and plenty of interesting rock formations. There are some tough trails in this section with lots of rocks, roots, and punchy climbs and descents. There is so much beauty surrounding you that you may be tempted to look around but keep those eyes on your feet - there are plenty of rocks and roots to trip you in this section.

4. Scotsdale Heritage Farm: Scotsdale Farm on the Niagara Escarpment is a 531 acre heritage farm bequeathed to Ontario Heritage Trust in 1982. The area includes heritage buildings and barns, rolling hay fields, ecologically sensitive forests, unique wetlands, and evidence of Indigenous settlements.

(The sections above will only be completed by the 50km participants. The sections below will be experienced by the 50km and 25km runners!)

5. Limehouse Conservation Area: The Limehouse Conservation Area includes dense, pristine forest and plays host to some of the area’s cultural heritage. Featuring twisting creeks and a small part of the famous Bruce Trail, the park preserves one of Ontario’s last old-growth forests. You can still find some remnants of the mill and old lime kilns, initially constructed in the 1840s. Perhaps the most unique section of this race course is found within the Limehouse Conservation Area where participants will find themselves WALKING through the "Hole in the Wall" and then climbing out on a wooden ladder. NO RUNNING THROUGH THIS SECTION (it is very short so take your time, look around, and take in the unique scenery around you).

6. Speyside Resource Management Area: Speyside's terrain is more rugged and seasonal weather regularly impacts large parts of this trail. During Spring, mud season can make some parts of the trail impassable however improvements have recently been made. The mature forest canopy provides a habitat for countless bird and animal species. Speyside is also known for its beautiful sprawls of wildflowers.

7. Dufferin Quarry Bridge: This bridge, which was completed in 1981 spans a large gap in the escarpment and can be seen from the highway over 3km away. This is a high bridge so if you are afraid of heights (like the Race Director is), don't look down!

8. Bruce Trail's First Blaze: participants will pass the location of the first blaze that was painted on the Bruce Trail in July of 1962 . Keep an eye out for the plaque!

As lifelong users of the Bruce Trail, we are please to help support them and we will be donating $20 from each registration directly to the Toronto Bruce Trail Club. As many of you know, the various clubs rely on these donations to help with their trail maintenance and improvements, which include building and repairing bridges, stairs, boardwalks, and stiles. The club also maintains the trail, removes fallen trees, and ensures that the trail is in excellent condition.

What does the race fee include:

-All participants will get race swag including a soft-spun t-shirt (and more!)

-Finishers will earn a finisher's medal.

-Race fee includes parking at Kelso Conservation Area

-Shuttle bus from Kelso Conservation Area (finish line) to the start line of the race (for 25k and 50k participants - 10k runners will complete an out-and-back course).

• An unforgettable adventure!

Runners will have the option to choose either a Unisex Shirt or a Women's Cut Shirt during the registration process. The title "Women's Cut" is the actual name of the cut. Any person is welcome to choose whichever option they wish. Please note, the women's cut shirts do tend to fit a bit small so you may want to size up.

50km Race Course:

The 50km race course is actually more like 51.8km. Participants will run the entirety of the Toronto Bruce Trail Club (50km) plus a little over a kilometre at the beginning and the end.

Part of what makes this course so incredible is the wide variety of terrain types on the course. Participants will experience lots of groomed trails where you can experience some magical running flow, challenging technical trails, rocks, roots, short sections of road, and plenty of short but punchy hills to climb and descend. There will be bridges, countless boardwalks, and stiles (small ladders to get over fences). The scenery will be beautiful and the course will be memorable. Did we mention rocks?

In our opinion, what makes this course challenging is not the elevation gain (about 800m for the 50km event) but rather the technical sections of the course, which will have even the most experienced trail runners walking through the most rocky sections.

Please keep in mind that participants will follow the permanently marked white blazes, which will be painted primarily on trees but also on rocks, and posts. The course is marked in a way that when you pass a blaze, you can usually see the next blaze. If you miss a blaze or can't see any blazes, don't travel more than 100m before backtracking. Please keep in mind that thousands of people follow these blazes successfully every year. If you go off course, it is usually because you are distracted or fatigued. A good rule of thumb is that the Bruce Trail marks where you SHOULD go and not where you SHOULDN'T go. By this we mean that unless you are clearly directed to turn, just stay on the trail that you are on and follow the white blazes. For the majority of the course, participants will find that there is only 1 trail to follow anyways.

We highly recommend buying and downloading the Bruce Trail app and/or downloading the following GPX file to your watch, if your watch has that capability. Here is a the data from the run that we did while mapping out the course in 2024:

FIRST BLAZE TRAIL RACE STRAVA DATA

25km Race Course:

The 25km race will actually be more like 27.5km and will start on Sixth Line between Silver Creek Conservation Area and Limehouse Conservation Area. Participants will get to experience one of the most unique trail running experiences in Ontario as they pass through the magnificent "Hole in the Wall", which will have runners travelling through a cave and then up a ladder. This section has the potential to get a little congested so please be patient and enjoy the unbelievable scenery that surrounds you.

Runners will have the opportunity to run through the Speyside section, which is beautiful but has some very rocky and rooty sections. Those of you that are trying to run fast will likely not enjoy the rocky section very much and will be cursing the Happy Trails Team, but those of you who are there to enjoy the experience and take in the scenery with some really cool people and don't mind slowing down through this part will love Speyside!

Participants will get to enjoy a wide variety of terrain types including beautiful flowing single track, countless bridges and boardwalks over and around streams and creeks, very challenging technical rocky sections, and a long stretch along the edge of the Niagara escarpments from which participants will be able to see Toronto on a clear day.

Runners will also get to run across the very high quarry bridge and will pass the site of the first blaze that was painted on the Bruce Trail.

This really is a stunning course but is also quite challenging. It will likely take longer than you expect but we are pretty sure that you are going to love this adventure!

There will be 3 aid stations along the way.

10 km Race Course:

The 10km race course will start and end at Kelso Conservation Area. There is plenty of parking (included) available for all participants.

The route will have participants running the final 5km of the 25k and 50k courses, in reverse, and then turning around and running back to the finish line. Please note, like the 25k and 50k courses, this is not your typical 10k race. It is hilly and there are some technical sections to the course.

There will be one aid station on the 10km course.

Aid Stations: There will be aid stations approximately 8-12km apart. The aid stations will be stocked with your typical trail race food (pickles, PB and J, chips, cookies, and other sweet and salty snacks), water, pop, and an electrolyte drink.

Please note that all Happy Trails Racing events are cup-less so you will need to have a collapsible cup or bottle to fill at the aid stations.

We recommend carrying at least 1L of fluids for this race.

SCHEDULE:

7:55am - The 50km race bus will depart Kelso Conservation Area. Don't miss it! The bus ride will be great; you will get to hear the RD ramble on during the pre-race briefing, you will get to hang out with other trail runners while they still smell good and, if time permits, perhaps we will even sing some camp songs!

9:00am - The 50km race will start from the Cheltenham Badlands. Let's gooooo!!!!

10:00am - Start of the 10km race from Kelso Conservation Area.

10:05am - The 25km race bus will depart Kelso Conservation Area. Similar to the 50km bus ride, the pre-race briefing will take place on the bus. The bus ride will be a little shorter but there may still be time for some camp songs. We'll see.

10:45am - The 25km race will start from Sixth Line between Silver Creek and the Limehouse Conservation Areas. Runners will cross the stile and be off on their merry way!

12:30pm- Potentially first finisher of the 25km event (estimation only).

1:40pm- Potentially first finisher of the 50km race (based on the FKT of 4:37 for the Toronto Section of the Bruce Trail- this race is 2km longer than that).

7:00pm- Race Cut-off

Refund Policy:

Happy Trails Racing has a great policy regarding race refunds/transfers: register with confidence knowing that you can take advantage of our early bird pricing and, if you need to back out, you can do so up to 30 days before the race with a 100% race credit that can go towards any future Happy Trails event. It doesn't expire. Unfortunately, we cannot accommodate cancellations within 30 days of the race. However, participants are welcome to transfer their bib to someone else without any penalty up to 5 days before the race. Please keep in mind that everything we need to order to have you at our race is done so at least 30 days out.

Welcome to the 2nd edition of the

Mudskipper SwimRun - Milton, Milton Open Water Swim, and the Inaugural

Milton Runs 7.5K and 15K Trail Run

At Area 8, Conservation Area

This event takes place in Milton, Ontario, just 1/2 hour west of Toronto, and close to many cities, including Hamilton, Guelph, Kitchener-Waterloo, Mississauga, Brampton, and Cambridge, to name a few.

NEW DATE

August 16, 2026

Mudskipper SwimRun - Milton

The 2026 Canadian Individual SwimRun Championships

This event features a 10K and 20K Individual Swimrun where participants will alternate between swimming in the Area 8 Quarry and running along the beautiful and challenging trails of Kelso Park.

Canaqua Sports is pleased to announce that the 20K distance of the Mudskipper SwimRun Milton has been named the

2026 Mudskipper Canadian Swimrun Championships,

Milton Open Water Swim

Come and join us for a swim in the beautiful Area 8 quarry, where we are anticipating water temperatures of 20 degrees.

Swimmers will do laps around our 1.5K course with distances of 1.5K, 3.0K, and 6K

NEW RACE

The Milton Runs 7.5K and 13K Trail Run

Run around the beautiful Area 8 Quarry before heading out to the Challenging backwoods of Kelso Park as you complete our 7.5K course.

The 15K race takes you through the course 2 times.

NEW TO CANAQUA SPORTS

Canaqua Sports is happy to announce that their local triathlon association is sanctioning this event and all of our Championship Series Events.

For those who are not members of a triathlon association, please register by using the Non-Members section. You will be asked to purchase a 1-day registration to participate in this event.

For Triathlon Ontario members, please enter by clicking on the event of your choice. You will be asked to provide your Triathlon membership number.

Any questions, email [email protected]

NEW FROM CANAQUA SPORTS

Save on Travel

Hotel bookings, Flights, and Car Rentals

Canaqua Sports announces a partnership with Sportsmasters Travel.

Save money when you book for your events, or even a non-sport trip.

Booking is Easy - Enjoy the Savings!

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Our Annual Charity Run in Milton,ON!

What is Run For Milton?

Mercy 4 Mankind, a subsidiary of the Ahmadiyya Muslim Youth Association (AMYA), is honoured to host a charity event to raise funds for the dedicated staff and courageous patients at Milton District Hospital. We are deeply moved by the selfless work of the doctors, nurses, and support staff who provide comfort and healing to those suffering from illness and injury.

Our charity run/walk event allows us to embrace the Milton community and provide support and encouragement to the Milton District Hospital.

We are thrilled to bring people from all backgrounds and abilities to participate in our inaugural "Run for Milton" for this worthy cause. Whether you are a competitive runner, a casual walker, or someone who simply wants to offer your presence in support, you are welcome here with open arms. Veterans, families, children and seniors - come one, come all!

Let us unite and take each step forward with empathy and compassion for our neighbours. The festive community atmosphere will remind us of our shared humanity.

We sincerely hope this charity run/walk event provides the Milton District Hospital, its care providers, and its patients with the necessary resources. Let's join hands in solidarity!

Event Details

Location - Milton Community Sports Park, 805 Santa Maria Blvd, Milton, ON L9T 2X5, Canada

Event Date - Sept 13th, 2026

Distance - 5KM Run / 1KM Fun Walk

Event Schedule

10:00 AM - Registration starts

10:30 AM - Opening Ceremony

11:00 AM - 5KM Run Start

11:15 AM - 1KM Family Fun Walk Starts

12:00 PM - Awards Ceremony

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Location

Share the Road Gran Fondo

Cycling connects us to our communities in unique and powerful ways. It’s more than just a mode of transportation—it’s freedom, joy, and independence. But today, too many cyclists face unsafe conditions on Ontario’s roads. This ride is about changing that.

By participating in the Share the Road Gran Fondo, you’re helping to create safer roads and communities for cyclists. Funds raised will directly support Share the Road Cycling Coalition's mission, from advancing safer cycling infrastructure to delivering education campaigns and advocating for meaningful change.

This event honors OPP Sergeant Greg Stobbart, whose tragic death while cycling in 2006 inspired the creation of the Share the Road Cycling Coalition. Greg’s story serves as a powerful reminder of why we ride—to create safer roads for everyone, ensuring no other families have to face such devastating loss.

On Sunday September 20th come to ride with us in Milton and the neighbouring municipalities to experience cycling in Halton Region. Our event prioritizes safety and will depart from the spacious Mattamy National Cycling Centre.

The event will feature an engaging pre ride and post ride expo and participants will have the option to chose between a 40km, 80km or 110km distance, featuring some of the best roads in Halton. The route will be full marked and will feature rest stops every 20-30km. Printed maps will be available at check-in.

Proceeds from the event support the ongoing work of the Share the Road Cycling Coalition, helping to advance cycling safety and advocacy across Ontario. Registration is $250, which includes a $125 charitable donation. Participants will receive a tax receipt for the donation portion of their registration.

Please contact greg@performancedrivenevents or [email protected] if you have questions.

🐾 Paws in Motion – Run/Walk for Rescue Dogs 🐾

MILTON ONTARIO Join Last Litter for Paws in Motion, a fun-filled community Run/Walk dedicated to giving rescue dogs a second chance at life.

Co Hosted By:

Nude Buddha Tattoo Milton

&

Murphy’s Own Dog Treats

Whether you’re an experienced runner, casual walker, dog lover, or family looking for a meaningful day out, this event is for you! Participants can run, walk, or cheer from the sidelines while helping raise funds for dogs in need of foster care, veterinary treatment, transportation, food, and supplies.

Enjoy a day filled with community spirit, adoptable dogs, local vendors, raffle prizes, family-friendly activities, and opportunities to learn more about rescue and responsible pet ownership.

Every registration, donation, and step taken helps provide hope, healing, and a brighter future for homeless and surrendered dogs waiting for their forever homes.

🐕 Bring your family, bring your friends, and bring your walking shoes!

Together, we can turn every step into a second chance.

Paws in Motion

Run With Purpose. Walk With Love. Save a Life.

We are proud to announce that this event is sanctioned by Athletics Ontario. --- We are thrilled to announce that we are partnering with La Sportiva for our events this year. Not only will La Sportiva be at our races with their demo fleet of shoes to try but they will also be giving away 2 pairs of shoes! --- PLEASE NOTE: THIS IS FOR THE 2026 EVENT This race is in support of MedVents - an amazing team that provide First Aid services at all of our events. Course Description: Come join us for one of our most popular events: The Beav. Hilton Falls Conservation Area is known to have some of the best trails around. This course is primarily made up of fast, groomed trails with some short but tougher and more technical sections thrown into the mix. The weather has been drastically different each year that we have put on the event. The first year, we had snow. The second year we had a cold day with high winds. Who could forget year three when a beaver built a dam and flooded a portion of the course

(yes, seriously). In 2022, we had a gorgeous day with sun and 15 degrees. Who knows what this year will bring? PLEASE NOTE: The course leaves Hilton Conservation area and enters Halton Region property from approximately 8k through 16k of the 25k loop. We owe a huge "THANK YOU" to the wonderful people at Halton Region for allowing us to use their trails, specifically the Britton Tract and the Robertson Tract. This section is an important part of the course and adds variety as well as some of the fastest runnable sections of the route. All participants in the 25k and 50k races will be required to sign an additional waiver, which will be given to you at race kit pick-up. --- For a map of the 25k loop that we will be using, please click here. For a GPX of the 25k loop, please click on the following: 25km Course GPX File To watch a video slideshow of the race course, please click on the link below: The 10km race is an out and back that will have participants run on the groomed trails around the

reservoir and over to the waterfall. From the waterfall, runners will then get to experience a short section of rugged and highly technical terrain on the Bruce Trail before reaching the falls. At the falls, participants in the 10km race will descend a set of stairs to the base of the fall where they will pick up a small pin with the Beav Trail Race logo on it (to prove that they went all the way to the bottom of the stairs). From here runners turn around and head back to the finish line. The 25km race will start with the same route as the 10k but instead of turning around, runners will continue on the Beaver Dam Trail, which inspired the name of the race. The remainder of the "out section" of the course is a pleasant mixture of single track and double track with some additional technical sections for runners to overcome before heading back towards the finish line. The 50km race will be the same as the 25k course but will be run twice. The 50km course will have a 9hr cutoff. Those who plan

on taking more than 8hrs should bring a headlamp or flashlight, just in case. It gets dark early at this time of year and the sun sets quickly. The timing of this race makes it perfect for runners trying to squeeze in one more race for the season or for those who want to try a new distance. Aid Stations: Although subject to change based on our permit, the aid stations are planned as follows: 10k race: Drink and S'mores Aid Station at 5k (this aid station has drinks and s'mores only) 25k race: 5k (drink/s'mores station), 8k (full aid station), 17k (full aid station), 20k (drink station) 50k race: same as 25k race but run twice with an additional aid station at 25k (start/finish area) Runners can expect the usual ultra staples- water, electrolyte drink, PB & J, sweet and salty snacks. All Happy Trails Racing events are cup-less so you will need to have a collapsible cup or bottle to fill at the aid stations. Pacers: Sorry, pacers are not permitted in any of the events. If you feel that you

will need a pacer, for safety reasons, please contact the Race Director before registering. Participants over the age of 65 can have a pacer if they wish. Race Apparel, Medals, and Prizing: Stay warm after the race with a custom hoodie that is included in the registration for the 25k and 50k events. (Please note: hoodie design is subject to change depending on supplier availability). Participants in the 10km event will receive a t-shirt with an option to upgrade to a zip-up hoodie during registration. Apparel shown is from our 2018 event. The apparel is different every year. Finishers will receive a custom finisher's medal. Prizes will be awarded to the top 3 in each race distance. Post Race Food: We understand that people have different dietary restrictions, needs, and preferences. Because of this, rather than include the cost of a post-race meal that you may or may not enjoy/ be able to eat, we do not include meals in our race registration fees. Refund Policy: Happy Trails Racing has a

great policy regarding race refunds/transfers: register with confidence knowing that you can take advantage of our early bird pricing and, if you need to back out, you can do so up to 30 days before the race with a 100% race credit that can go towards any future Happy Trails event. It doesn't expire. Unfortunately, we cannot accommodate cancellations within 30 days of the race. However, participants are welcome to transfer their bib to someone else without any penalty up to 5 days before the race. Please keep in mind that everything we need to order to have you at our race is done so at least 30 days out. Also, please note that we don't have waitlists. If spots open up they will be available on Race Roster so check back occasionally. --- RACE REPORTS: --- All photos care of Sue Sitki Photography