Winter Hill, LLC

Longwood Equestrian Programs

Longwood Riders- Team and Private Training Opportunities


Facility Fee - $1200 per semester

Includes 30 rides per semester for use in lessons, team practice, captains practice, classes at home shows, on farm clinics, and independent rides.  

*5 Team Practices included in package*

*2-4  "barn hours" per week required*

(barn hours may include feeding, cleaning, grooming, etc. and will be assigned in shifts of 2 riders).

Two (2) Longwood Equestrian Barn Captain positions available with package discount applied ($300 credit toward package). You can email a cover letter to describing why you would like this position and why you are a good candidate to have a leadership role at the barn.  All letters will be reviewed by Coach KC as well as Alumni riders, and any other advisors to barn activities.

Additional Team Practice with Facility Package OR Winter Hill Board: $25/rider

  • work as a team group
  • drills
  • position practice
  • strengthening
  • problem solving 
  • collaborating with captains and Instructor 
  • 1-3 hours depending on size of group and agenda
  • team practice required for show riders during show season and lessons (see below) may be required based on rider level, experience, or needs.

Lessons with Facility Package OR with Winter Hill Board: $45/rider

  • private, semi-private, or small group
  • time varies depending on size and agenda 1/2-2 hrs depending on size of group and agenda
  • focused training for horse and rider
  • extra help, horse show prep, etc.

Lessons/Clinic with KC outside of Facility Package on or off farm: $65/rider

*TEAM riders have the ability to fundraise reimbursement for out-of-pocket expenses.

Recruit School - $150 (new riders only, no fee for returning riders)


FRIDAY PM & SATURDAY AM   Please make sure to ask KC or a Captain to plan ahead for this requirement. 

Please contact KC via email or Facebook to be added to the Recruit page.  We look forward to hearing about your experience, goals, and questions you may have.

Recruit school is a pre-requisite to all lesson programs and will be held very early in Fall semester.  

The fee for Recruit School is $200

(This fee is only required for new riders, returning riders in good standing participate for no charge and attendance is a prerequisite for participating in a semester package).

Working Student Opportunity - $10/hr

Find out more

Show Expenses

Riders are responsible for all show expenses including entries, Coaching, Horse Use, Shipping, Stabling , etc. 

IHSA Show entries are usually about $40 per class.  Coaching is $250 per day (per team, split by riders or fundraised) for team shows and outside show coaching may vary.

Fundraising Opportunities

Longwood students have unlimited potential to fundraise to cover their out-of-pocket expenses! 

Lease Program


Leasing Considerations

Riders who aspire to show in our local, Regional, Zone, and National circuits may want to consider leasing a show-type horse in lieu of a lesson package on school horses who generally stay at home.  Leasing commitments can vary from 3xweek to a full lease with daily access.

On-Farm Lease of Winter Hill Horse

Half Lease: $750

3x week access, priority horse use at shows, no horse use fee at shows, competitive show horse in appropriate divisions.

Full Lease: $1500

Full time access, expenses of horse included (board, shoes, teeth, vaccinations, etc).

Lease riders are required to lesson weekly as well as arrange a training ride weekly if needed.

Outside Lease horse as Boarder

If a Longwood Equestrian rider would like to arrange a lease of an outside show horse to meet their needs and goals we work with trainers all over the country to provided horses for this program.  Generally an annual lease fee is negotiated to owner of the horse, and student is responsible for all horse expenses as a boarder at Winter Hill.  

Working Student



Longwood Equestrian students who are boarding or participating in a regular riding program at Winter Hill are eligible to apply for a working student position.  Work varies and students must be reliable, hard working , and willing to improve and set a great example for everyone in the barn. 


Schedule will vary depending on farm needs.  We will try to arrange work opportunities around your scheduled time at the barn. 


Working student's are paid $10 per hour via Venmo private payment.