We each have a spot or two where we ride that we consider magical. These are the kind of places where we feel at peace, where we feel free on the bike. Riding is not only sport and transportation but also experiencing new places, about sharing the experience and better discovering oneself. 

Dede Barry is a co-owner of Mariposa Bicycles,  a 2004 Olympic  Silver medallist in cycling and currently lives in Toronto, Canada.  She rides regularly on the trails and roads around the city on her Mariposa bicycles and her cycling has taken her around the world.  Here are a few favourite places to ride in the cities where she has resided: Milwaukee, Boulder, Girona and Toronto: 

Not all of us have the luxury to ride all day every day. Most of us work to squeeze in an hour or two  Being a mom of two boys and business owner, I am now more time crunched than ever. My little loops around the city, and through its parks, in the early morning hours keep me happy and healthy. Through my life I’ve had the benefit to have ridden a bike in some wonderful places, quite often discovering some great routes.

My introduction to cycling in the late 1980s was through my Speedskating coach, former Olympic medalist and anesthesiologist, Dr. Mike Woods.  At his advice, I began riding my bike in the off-season for training and entering local races  in the summer months. He coached a group of high school kids and we all trained together.  As time crunched students who were engaging in multiple sports, the focus was to maximize fitness gains with less than 2 hours of training per day.  Nearly all of our rides were under 50K and we always rode a solid tempo. We never rode “easy” or road “junk miles”. As, we lived in the Midwest, there were no mountains to train up, but our fitness helped us on all terrain. Intervals, hill sprints, time trial efforts and paceline riding got us fit and our little team was quickly winning races at national and international levels.

After a couple of years of racing, I was offered my first professional contract and moved to Colorado. I began riding the mountains each day and doing rides consistently over 100K.  I improved with age, experience and training, but I believe that for the time crunched cyclist it is possible to reach high fitness levels with less than 50KM of riding per day and for everyone, a daily escape on the bike is good for the mind and body. Towards the end of my cycling career, when I returned to university I squeezed in a decent but short ride early in the morning before rushing off to class. Despite not riding the same number of hours in the past, I was able to race competitively at the international level.

I have moved around a lot over the years, but one commonality in all the places I have lived has been finding good cycling routes that are under 50KM.  My riding these days is no longer focused on trying to become race fit.  It’s more about taking a break from the daily routine, immersing myself in green space, clearing my mind, enjoying solitude or the company of friends.

Here’s are a few of my favorite Rides Under 50K from the places I’ve lived:

Route 1:  Milwaukee Lakefront  42.3km, 187 m elevation

Starting locally owned Collectivo Cafe, where I’ll often meet  few old friends, this loop takes me along the lakefront past Bradford Beach and then climbs up onto the bluff and passes by the beautiful historic mansions of the East Side of Milwaukee.  As the routes takes me north, through the suburbs of Whitefish Bay, Fox Point and Bayside, there are a few town signs to sprint for (something I’ll do when I ride with Michael or  one of our sons) to determine who pays for the post ride custard (Wisconsin Ice Cream).  A diversion down Beach Dr. takes to you what was known as “The Witch’s House” among the children when I was young.  It is the historic home of Milwaukee artist, Mary Nohl, whose house and yard is adorned with concrete sculptures of dinosaurs, fishes, monsters and other art.  After her death in 2001, it was made a historic site and is currently under the care of the Kohler Foundation. Her art work is remarkable and well worth seeing.

The climb back up the bluff from Mary Nohl’s house is a 7% grade, which is where I did hill sprints when I was younger.  I brought our son there last August while visiting and he managed 7 repeats–watching him thrash up the hill brought back a whole pile of memories.

At the top of the hill, a sharp left turn brings me back to Lake Drive and eventually to Collectivo Coffee. The waterfront is ideal for spinning the legs and enjoying the views.

Route 2:  Boulder, CO – Gold Hill, CO 35.8KM, 1,015 meters of climbing

Starting the iconic Trident Cafe in the centre of Boulder, this ride travels up Boulder Canyon along a gravel bike path to 4 Mile Canyon.  Although the base of 4 Mile Canyon is paved it turns to gravel near the top, when the road gets a lot steeper. Overall, the average gradient is 15% over approximately 15 Km. It’s good a challenge but well worth it for the views and the pastries, drinks and, in the winter, warm fire at the Gold Hill General Store at the top. The old mining town has a rich history and is full of interesting and eclectic citizens. The descent into Boulder is steep and fast. It is mostly paved but has some gravel sections, with some tight switchbacks and views to Boulder, Denver and the Front Range.  It’s a blast. Don’t be fooled by the short distance, your legs will be ready a cold dip in Boulder Creek and a beer when you reach Boulder.

Route 3:  Girona – Els Angles, Spain 40.3 Km, 820 m Elevation

The route starts in downtown Girona by the river in the old town at the Boira (meaning fog in Catalan) Cafe. For the decade we lived in Girona, we would meet our friends and teammates there  before we rode and fuel up with a cortado (short coffee) and a  bocata amb tortilla (egg sandwich).

The route goes up Montjuic and down the backside to Campdora on a tight, twisty paved descent and then through the towns of Celra, Sant Marti Vell (which has a lovely farmers market) and Madremanya to the base of Els Angels.  The steep 6 kilometer climb to Els Angels leads to a church and monastery where Salvador Dali married his wife Jacqueline.  With views of the Mediterranean Sea, the Costa Brava, Girona and the high Pyrenees, you will want to spend some time there exploring and have lunch or dinner at the monastery. It’s also a good stop for lunch, a drink or snack as the restaurant serves traditional Catalan breakfast, lunch and dinner.

The descent into Girona is windy and fun and drops straight into Girona.

The Onyar River, Girona, Spain.


Nearing the top of Els Angels.


The church where Salvador Dali was married.


Route 4:  Toronto Ravine Ride, 35 km, 7 hills and 330 m of elevation.

In Toronto, I start most rides at 5 am, while the city is still sleeping.  It means that roads which would not be rideable much of the day are clear. It’s an opportunity to start the day with some solitude.  This route has 7 hills and makes for a good morning workout.

Lush green and full of wild animals, the Don Valley Ravine Cycling trails are an escape from the noise and pace of the city.  The beauty of riding the Don Valley Cycling Trails on an all-road, cross or mountain bike is that there are multiple diversions you can take on dirt, single track and gravel to change up or extend this ride.

From home, I travel down the Bayview Extension to Rosedale Valley Road.  The climb Rosedale Valley Road warms you up for MacClennon Ave, Beachwood, Thorncliff, The Science Centre Hill, Sunnybrook Hospital Hill and Crestwood which lie ahead.  If you are feeling perky, you can extend the ride with repeats on Crestwood Hill.

We often end the ride on Bayview with a quick coffee and pastry at Lit, a locally owned shop.


9 thoughts on “Favourite Rides: Rides Under 50K

  1. One of the most delightful trails very close to Toronto is the Caledon Trailway. Very few seem to know of how easy it is to attain by GO train/bus at both ends, albeit some on-road cycling is necessary at each end. I’ll post GO details later, I’ve worked out a way to connect at each end just catching the last train in from Mt Pleasant to Union.

    The trail is in amazingly good shape considering many southern Ontario trails are suffering from water damage this year (the clay gets washed out and leaves unstable grit in spots, or the opposite, the grit is gone and the clay is slippery and pliable). Much of the Caledon Trailway was relaid last year with optimal crushed limestone with a binder to keep its form.

    The trail itself can easily be done in two hours, albeit longer gives more time to sight-see along the way. Stops for refreshments are available in at least three villages/towns on the route. By using GO, there and back the trip can be done from late morning (first train out is about 10:00 am from Union to catch Bolton bus at Malton Station) and bus at Georgetown to catch last train in from Mt. Pleasant is just after 3:00 pm. Being a rail-trail, grade is maximum 2%. Very easy to maintain pace, and road tires (25-28c) are optimal on the trail surface.

    Rather than trying to past in a map or more directions, Google: “Caledon Trailway”. Be advised that some of the pics that show are older, and crushed limestone is now intact from Mt Hope Rd (best way up from Bolton) and the western end of the trail.

  2. Hi Dede
    Thank you for a wonderful article.
    We now live in Collingwood and the beauty is that there are so many rides right from our door; from jail trails to steep terrain on both gravel and asphalt. Every day I can decide on a trail and pick the gravel or road bike. Getting old has drawbacks,but, being able to cycle a lot is not one of them.

  3. I remember reading in Le Metier that young Michael Barry would head out on a 50 km WARM-UP ride BEFORE a stage of the Tour de France. It beggars the imagination! I go on a 50 km ride and I sleep for an hour! Great book by the way.

    V. good description of the Don River Trails. Don’t forget Taylor Massey Creek and the Humber River Trails. You can ride 25 km from Lake Ontario to Steeles Ave. , then along the hydro corridor to the Don River and back down to the lake. That makes a great ride.
    For a west-end cyclist with a 15-km deadline, I like riding up the Lake Iroquois shoreline aka the Davenport Ridge from the Annex to St. Clair and then tootle around Prospect Cemetery and the hills west of Dufferin and Eglinton. There are some steep hills and lovely trees with very few cars.

  4. Hello Dede

    Great rides — but … have you done a 50 mile ride on a hobby horse? The photo I am trying to attach (unsuccessfully) is of 8 of the 13 riders who rode hobby horses and draisines from Nancy in France to Karlsruhe in Germany (240 km) in 5 days. In the picture – that is me in the middle wearing my Mariposa bike shorts!!

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