-
About
- About the Academy
- Administration
- Annual Report
- Awards & Recognition
- Board of Trustees
- Business and Community Connections
- Calendars
- Communications
- Compliance (Policies)
- Current 8th Graders
- Directory
- History
- Mission & Vision
- Pinkerton News
- Social Studies Wing -- Building Project
- Start Time Committee Information
- Strategic Plan
- Technology
- Academics
- Admissions
- Alumni
- Athletics
- Careers
- Clubs & Activities
- Stockbridge Theatre
PROGRAM FULL - WAITLIST OPEN
Gunstock Outreach Program 2027
Join the Pinkerton Academy Ski Club for four Friday ski and snowboard trips to Gunstock Mountain Resort in Gilford, New Hampshire!
The Gunstock Outreach Program includes discounted season pass options, free ski and snowboard rentals, optional lessons, and transportation from Pinkerton.
Program Dates
January 8, 15, 22 & 29
Four Fridays in 2027
Program Cost
$350–$550
Based on pass type and registration date
Final Registration & Waitlist Deadline
November 14, 2026
No registrations or replacements
after this date
Program Capacity
150 Students
Registration available while spots remainCurrently Full - Waitlist Available
Gunstock Outreach RegistrationRegistration AvailabilityRegistration Full0 of 150 spots remaining150 registrations received150 total spots
Registration Open
Spots are available for the 2026–2027 Gunstock Outreach Program. Complete the registration form by November 14, 2026. All registrations and replacements must be finalized by that date.
Program Full - Waitlist Open
The Gunstock Outreach Program has reached its registration limit. Interested students may join the waitlist through November 14, 2026.
If a spot becomes available before the deadline, families on the waitlist may be contacted with instructions for registration and payment. Joining the waitlist does not guarantee a spot.
No registrations, waitlist submissions, or replacements will be accepted after November 14, 2026.
About the Program
Pinkerton Academy participates in Gunstock Mountain Resort's Friday night Outreach Program. Students travel by bus from Pinkerton to Gunstock for evening skiing and snowboarding.
Each participant purchases a discounted Gunstock season pass, which can also be used throughout the ski season according to the benefits and restrictions of the selected pass.
Students may bring their own equipment or use the free rental service offered through the Outreach Program. Optional ski and snowboard lessons are also available.
Beginner Disclaimer:
Although lessons are available, students
who have never skied or snowboarded
should not register for this program.
Lessons last only 50 minutes, after
which students ski or ride independently
for the remainder of the evening.
Program Dates & Schedule
| Date | Program Time |
|---|---|
| Friday, January 8, 2027 | 2:30 PM – 10:00 PM |
| Friday, January 15, 2027 | 2:30 PM – 10:00 PM |
| Friday, January 22, 2027 | 12:00 PM – 10:00 PM |
| Friday, January 29, 2027 | 2:30 PM – 10:00 PM |
| Makeup Date | To Be Determined |
Important:
January 22 has an earlier departure time
than the other three program dates.
Please plan accordingly.
Program Pricing & Pass Options
The total program cost includes two separate payments: a discounted Gunstock season pass and a $150 Pinkerton transportation fee.
Tier 1: Early Registration
Available through October 24, 2026.
| Pass Type | Gunstock Pass | Bus Fee | Total |
|---|---|---|---|
| Midweek Pass | $200 | $150 | $350 |
| Winter Prime Pass | $350 | $150 | $500 |
Tier 2: Regular Registration
Available October 25 – November 14, 2026.
| Pass Type | Gunstock Pass | Bus Fee | Total |
|---|---|---|---|
| Midweek Pass | $250 | $150 | $400 |
| Winter Prime Pass | $400 | $150 | $550 |
Midweek Pass
Valid Monday through Friday, subject to blackout dates and other pass restrictions.
This is the lower-cost option for students who primarily plan to ski during the week.
Winter Prime Pass
Provides unrestricted season access with no blackout dates.
This option offers greater flexibility for students who also plan to ski on weekends, holidays, or vacation days.
Additional Fee:
Families paying the $150 transportation
fee through MySchoolBucks will be charged
an additional $7.65 service fee.
This fee is not included in the
program totals shown above.
Registration & Waitlist Information
Registration Open
Students may register while spots remain, through November 14, 2026. Registration and all required steps must be completed by that deadline.
Registration Process
Complete the Pinkerton registration form, purchase the Gunstock pass using the instructions provided, and pay the Pinkerton transportation fee.
The Gunstock Outreach Program is Full
Students may join the waitlist through November 14, 2026. If a vacancy occurs before the deadline, families may be contacted with instructions for completing registration and payment.
No registrations, waitlist submissions, or replacements will be accepted after November 14, 2026.
Registration Process for Accepted Students
Students offered a spot from the waitlist before November 14 must complete the following registration and payment requirements.
Complete Pinkerton Registration
Complete the Pinkerton Academy registration form. Once submitted, follow the instructions you receive for purchasing your Gunstock season pass.
If your student is offered a spot from the waitlist before November 14, you will receive instructions for completing the required Pinkerton Academy registration forms and purchasing the Gunstock season pass.
Purchase Your Gunstock Pass
Follow the link provided by email to complete registration and payment directly through Gunstock.
Important Instructions- Parents must create or use their own Gunstock account.
- Students must be added to the parent's account.
- All passes must be purchased through the parent's account.
- Select either the Midweek Pass or Winter Prime Pass.
- Choose the appropriate rental package or select "No Rentals."
- Choose a lesson package or select "No Lesson."
Rentals and lessons are included at no additional cost with the Outreach Program pass.
Pay the Pinkerton Bus Fee
A separate $150 transportation fee is required for all participants. Families select their preferred payment method on the Pinkerton registration form.
Payments may be made by cash, check, or MySchoolBucks.
Final Registration & Waitlist Deadline:
November 14, 2026
All registration and waitlist submissions must be received by Saturday, November 14, 2026.
Students on the waitlist may only be offered a spot if an opening becomes available before this date.
No new students will be added to the program or waitlist after November 14, 2026.
Transportation & Bus Payments
Transportation to and from Gunstock is provided through Pinkerton Academy. The required transportation fee is $150 per student.
| Payment Method | Total Bus Payment |
|---|---|
| Cash | $150.00 |
| Check | $150.00 |
| MySchoolBucks | $157.65 Includes $7.65 service fee |
Cash & Check Instructions
Cash and check payments should be submitted to Mr. Konstant in the Senior Office (English Building).
Checks should be made payable to Pinkerton Academy. Include the following in the memo:
- Gunstock Bus Fee
- Student's Name
- Student's Pinkerton ID Number
MySchoolBucks Instructions
Families selecting MySchoolBucks will receive an email after November 14, 2026, with instructions for completing the bus payment.
Save on Service Fees:
Families who pay by cash or check
avoid the additional $7.65
MySchoolBucks service fee.
Transportation Requirement:
Students must ride the Pinkerton bus
to and from Gunstock.
Parent pickup at Gunstock may be
permitted on a case-by-case basis.
Students who do not ride the bus
to Gunstock will have their pass
disabled for that program evening.
Equipment, Lessons & Safety
Equipment Rentals
Ski and snowboard rentals are included at no additional cost with the Outreach Program pass.
Students who need rentals must select the appropriate package during Gunstock registration.
Optional Lessons
Lessons are free with the Outreach Program pass.
Lessons run from 6:30 PM to 7:20 PM. Students who register for lessons are required to attend them.
Helmet Requirement
All students are required to wear a helmet while skiing or snowboarding.
Students without a helmet will not be permitted to ski or ride. Gunstock offers helmet rentals for an additional fee.
Winter Sports Eligibility
Students participating in a Pinkerton winter sport may not participate in the Gunstock Outreach Program.
Athletic practices and games take priority over Ski Club.
Season Pass Pickup & Reuse
Students who participated in previous years must reload and reuse their existing Gunstock season passes.
Gunstock charges a $5 fee for replacement passes. Follow the registration instructions to add an existing pass to your account.
Outreach Pass Pickup Nights
Pass Pickup Night
December 2, 2026
Pass Pickup Night
December 6, 2026
During these events, students may pick up their passes, complete rental fittings, and ski.
Recommendation:
New passes should be picked up before
January 8, 2027. Students who wait
until the first program night may
experience long lines.
Once activated or reloaded, season passes may be used throughout the ski season according to the selected pass's restrictions and benefits.
Registration Materials & Resources
Review the following resources before completing registration or joining the waitlist.
Student & Family Guide Step-by-Step Registration Guide Gunstock Outreach FAQ Gunstock Ski & Ride Ability Chart Tier 1 Season Pass Benefits Tier 2 Season Pass BenefitsFrequently Asked Questions
Is the Gunstock Outreach Program appropriate for beginners?
No. Students who have never skied or snowboarded should not register. Although lessons are offered, they last only 50 minutes. Students must ski or ride independently for the remainder of the evening.
Are ski and snowboard rentals free?
Yes. Equipment rentals are included with the Outreach Program pass. Students must select the appropriate rental package during registration. Helmet rentals have an additional fee.
Are lessons included?
Yes. Optional lessons are included at no additional cost. Lessons run from 6:30 PM to 7:20 PM. Students who register for lessons must attend them.
What is the difference between Midweek and Winter Prime passes?
Midweek passes are valid Monday through Friday, subject to blackout dates. Winter Prime passes offer unrestricted access without blackout dates.
Can I use my pass outside the four Outreach Program dates?
Yes. Your Gunstock season pass can be used throughout the ski season, subject to the restrictions of your selected pass.
Do I have to pay Gunstock and Pinkerton separately?
Yes. The season pass is purchased directly through Gunstock. The $150 transportation fee is paid separately to Pinkerton Academy.
Can I pay the bus fee online?
Yes. MySchoolBucks is available for bus payments. The total online payment is $157.65, including a $7.65 service fee. Cash and check payments are $150.
Can parents pick up students directly at Gunstock?
Parent pickup may be approved on a case-by-case basis. All students are required to ride the bus to Gunstock.
Can students participating in winter sports join the program?
No. Students participating in a Pinkerton winter sport are not permitted to participate because athletic practices and games take priority.
Can I still join the Gunstock Outreach Program?
Yes. Registration is available while spots remain, through November 14, 2026. All required registration steps must be completed by that deadline.
The program has reached its registration limit. Students may join the waitlist through November 14, 2026. A spot may only be offered if one becomes available before that deadline. Waitlist placement does not guarantee participation.
Do I need to pay anything to join the waitlist?
No payment is required to join the waitlist. If your student is offered a spot before November 14, 2026, you will receive instructions for completing registration and submitting the required payments.


