Winter 2023/2024 registration is now open!

We are excited to announce that registration is now open for the 2023/2024 Chester Winter Program! While this may seem early to begin to think about skiing and snowboarding, winter will upon us soon enough and we have a lot of amazing programming planned. Please take a second to read through this email and be sure to pay attention to the info about registration and scholarships as those aspects of the program have changed this year.


You need to complete a Google form if you plan on renting ski or snowboard equipment, and/or if you are requesting a scholarship (even if the scholarship is for just a season pass). Families only need to complete this form once, so please communicate with your partners to avoid submitting multiple entries. If you are getting a season pass only, and are NOT requesting a scholarship, then you do not need to register. When you register, you will identify how many season passes, how many sets of equipment, and what equipment you will be renting. If you are requesting a scholarship, you will also do that as part of this registration and will identify your family size and income range. There is more info about scholarships below. Once you click “Submit” you are registered.

Registration is open starting Tuesday, 9/12/23 and will close Monday, October 9 at 9am. You can register any time in that window. After that point, if you miss the deadline to sign up, you will have to sign up for any available ski fitting appointments once we post it to our website starting on October 16, and your family will likely not have access to scholarship funding, as we expect that it will have all been awarded.

You can register now at this link:

Costs & Payments

The costs of this year’s program can be found by following this link:

You will notice that there are more categories this year for season passes and rentals. To determine your family’s costs, you must first find the number of season passes you are purchasing, then find the number of equipment rentals, and then you can follow the row over to find your initial cost.

There are several different payment options you may choose:

  • Credit Card/ Debit Card- this is a new option, and please note that there will be a surcharge to cover the processing fees
  • Cash
  • Check
  • Payment Plan: You must provide Chester Bowl with three pre-written checks when you check out. Your total cost will be divided into three payments. The first check is due and dated at the time of your equipment fitting. The second check will be dated and deposited on January 15, and the third payment will be dated and deposited on February 15.


The scholarship support is designed for families with lower income that are unable to afford to participate in our programs without financial support. This season, the scholarship funding is limited to $25,000. If your family is requesting a scholarship, please complete the winter program registration form before the 9 am October 9th deadline. Families will be notified of the scholarship amount they can expect before equipment fittings. Scholarships will be awarded based on need and will be awarded first to families that completed their volunteer hours last season and new families.  Families may be responsible for a portion of their rental fees even if they are requesting a full scholarship. You can see a full explanation of the changes to our scholarship program and the reasons for it here:

Equipment Fittings

We have a limited amount of gear that is rented out for the season on a first come, first served basis. Families will sign up for individual ski or snowboard fitting appointments.  On October 10 a link will be emailed out to families that completed their hours from last season or are new to the program. The link will be mailed out on October 13 to families that did not complete their volunteer hours last year. This link will let everyone watch a winter slideshow summarizing all the different programming we have planned for the winter. At the end of the presentation, there will be a link to a Signup Genius page where families can sign up for ski or snowboard fittings.

Once signed up, families will come to Chester on their scheduled fitting night in late October or November, get fit for their gear, put it in their cars, and then pay for that equipment. They then take that gear home with them, wait (patiently?) for snow, and then ski at Chester and our partner organizations all winter long!

Equipment returns are April 22-24. Please put these dates in your calendar now, because if you miss these return nights you will be in the last group to sign up for equipment fitting nights during the 2024/2025 season.

Season Pass Benefits

Our season passes come with free lift tickets and deals at our partner resorts including: Mount Ashwabay, Giants Ridge, Mont du Lac, Lutsen, Mount Ski Gull, Whitecap, and Spirit Mountain. Details on the benefits are still being confirmed for 2023/2024.

There’s a lot of info in this email and can be a lot to absorb especially if you are a new family. Please email if you have any questions. If you know of any families that would benefit from learning to ski or snowboard, please share this email with them or encourage them to visit our website. We are looking forward to having a great winter with all of you.