Team Maywood Cycling

Team Maywood offers participants group cycling rides from early May through late August.


About the Program

2024 Ride Schedule Coming Soon

View Maywood Events Calendar (for ride updates and cancellations)

Monday evening rides

Our weeknight evening rides start and end at Maywood Environmental Park in Sheboygan. Rides leave promptly at 5:30pm. Various riding levels are offered. Each level rides with a skilled volunteer trainer who provides instruction on riding skills appropriate to that level of cycling. Distances will vary from 10-20 miles, based on the riding level, weather conditions, and route selected. Monday evening rides have a no-drop policy, meaning you will ride with your group the entire time. Monday evening rides may also have prize drawings for bicycle gear and equipment.

Saturday Morning rides

Weekend rides provide the opportunity to build your endurance on longer routes. At least two ride lengths will be offered. Participants are encouraged to ride in pairs or small groups of a similar riding pace and ability. A catered rest stop is offered at the mid-way point of these longer routes and SAG service is available.

Check back for program benefits including discounts at area bike shops.

Corporate Wellness Info Coming Soon

Team Maywood is an excellent opportunity for corporate wellness programs and insurance programs that offer incentives for participating in fitness activities. Contact us for additional information on how we can work with your company to provide this opportunity to your employees.

Riding Levels

Note: If there are a large number of participants in a group, the group may be split into subgroups to allow for safer riding.

Group 1: This level is designed for the beginning cyclist or the cyclists who is looking for rides at a more relaxed pace. An emphasis is placed on safe individual riding skills and introduces safe group riding practices. An excellent choice for those looking to ride with others at a relaxed and slower pace.

Group 2: This level rides at a slight faster pace than Group 1. Cyclists in this group should have strong safe individual riding practices. Emphasis will be placed on group cycling. Drafting will be worked on with limited rotation riding.

Group 3: In Group 3, there is a greater emphasis on group riding skills such as drafting. Cyclists in this group should feel comfortable riding in closer proximity to other participants at a moderate riding pace. Rotational riding will be offered as an option.

Group 4: This level expands on the riding skills of group three. Participants should be strong in both individual riding and group riding skills.

Group 5: Riders are this level should be highly skilled in group riding and able to maintain a fast riding pace throughout the rides. Rides will include structured workout options.

Group Riding

The weeknight evening rides use a no drop policy. At times this requires faster paced riders to slow down to the pace of the group. The riding groups also stop to assist any rider in their group who may need help during the ride. Examples include fixing a flat tire, reattaching a chain, or stopping for a medical need.

Weekend rides offer cyclists the opportunity to ride individually, with a partner, or in small groups at their own pace.


2024 Ride Options and Pricing

Full Program Registration
Includes all weeknight evening and weekend rides
Maywood Association Member $165
Non-member $200


Monday Evening Rides Only
Includes all Monday evening rides
Maywood Association Member $135
Non-member $160
Add on Season-end Ride (August 23) $15


Weekend Rides Only
Includes all Saturday morning rides
Maywood Association Member $60
Non-member $90

Become a Maywood Association member to receive the discounted member rate. Membership start at $25 and cover all members of your household (at one address).

Additional Program Information

Read our Frequently Asked Questions document to learn more program specifics.

Weather Cancellations

Safety is the first priority on all our rides. We reserve the right to cancel a ride should weather conditions make riding unsafe. Examples of unsafe weather conditions include heavy rain, thunderstorms, heavy fog, extreme heat, and extreme cold. We do not reschedule or refund Monday evening rides that are cancelled due to weather. Should you choose to cycle after a ride has officially been cancelled, you are doing so on your own and without the support of the Team Maywood program.


Weather cancellation announcements are provided in several ways. After 3:30pm, we will email all participants if there is a weather cancellation. We will also post the cancellation to our website events calendar and on Facebook. If you are unable to access any of these sources, you may call the Ecology Center for an update. Please keep in mind our phone staff and volunteers leave for the day at 4pm.


Refund policy

Refunds, less a $25 processing fee, must be requested by April 22, 2024. After April 22 we do not refund any portion of the registration fee. You may transfer your registration to another individual.



Participant Expectations

As a participant of the program, there are several expectations of you:

  • Have your bicycle in good working order before each ride. We strongly recommend having your bike checked over by one of our area bike shops. While we will have basic tools for tasks like inflating tires, our volunteer trainers and staff are not able to repair your bicycle at the program.
  • Have your bicycle fit before the program begins. Area bike shops can assist you in adjusting seat height and tilt, handlebar height, and other parts of your bicycle to ensure a comfortable riding experience.
  • Wear a properly fitted helmet on all rides. Helmets are mandatory.
  • Obey all State of Wisconsin cycling laws and any safety guidelines put in place by Maywood. This includes riding no more than two abreast on all roads and not impeding the flow of traffic when group riding.
  • We strongly encourage the use of taillights on your bicycle or helmet. This greatly improves your visibility to drivers on the road.
  • Be respectful of our trainers and staff. Our trainers volunteer their time and make this program possible. If you have a concern with your riding group, please talk with your trainer or one of the program coordinators.
  • Carry emergency contact information on every ride and have a contact who can transport you if needed.
  • We rely on our participants to know their limits. If you are not feeling well, you may want to ride with a slower paced group or skip the ride.
  • Lock-up your personal belongings when out on rides. Maywood is a public park. Maywood is not responsible for your personal belongings. Do not leave personal belongings in unsecured vehicles or outside of vehicles.
  • As with all our Maywood programs, we ask that your follow COVID safety precautions. If you have symptoms of COVID or have known exposure to COVID, you may not participate in Team Maywood until the CDC recommended quarantine or isolation period has passed.

Supplies Participants Should Use or Carry on Every Team Maywood Ride

  • Wear a properly fitted helmet
  • Two filled water bottles
  • Identification and emergency contact information
  • A cell phone (unless you do not own one)
  • Medication or snacks you may need during the ride
  • A spare tube for your specific tire or patch kit and a way to inflate the tire


Additional Recommended Supplies

  • Eye protection (sunglasses, clear glasses, etc)
  • Cycling gloves
  • Tail light that attaches to your bike or helmet
  • Additional clothing layers should weather call for it
  • Plastic sandwich bag for your phone or wallet if it rains
  • Seat pack or other way of carrying supplies on your bike