Catamount's First Winter in the Bear Den Alliance: What the New AIM High Pass Means for Hillsdale Skiers

Catamount has a new ownership structure this winter, and the mountain looks much the same. The Schaefer family still runs it, the same general manager is still in charge, and the 44 trails along the New York and Massachusetts line are unchanged. The biggest change is the season pass. The adult version cost $599 when it launched in March and costs $799 today. Catamount's posted price table ends on November 30, three and a half weeks from now.

The same people at the Hillsdale end of Route 23

On March 23, 2026, Catamount and Berkshire East announced they were joining Bear Den Partners. Bear Den is an independent mountain ownership group founded by Ken Graham and Jon Schaefer. Bear Den formed in 2025, bought Vermont's Burke Mountain in April of that year, and announced an ownership transition with Smugglers' Notch Resort on February 11, 2026.

Hillsdale residents with a long history at Catamount will recognize the leadership. The Schaefer family has owned Berkshire East since 1976 and Catamount since 2018. According to Catamount's announcement, both mountains keep their existing leadership structure. General Manager Mark Smith stays at Catamount, and Melissa Roberts continues as chief financial officer for both resorts. Jon Schaefer described the move in the same release:

"This step represents an evolution for my family, not an exit."

The four mountains now operate as the Bear Den Mountain Alliance. They share resources, operating expertise and long-term capital, and each keeps its own management and identity. When MassLive asked Schaefer about the Vermont mountains in March, he promised gradual improvements, nothing drastic enough to change either mountain's character. For Smugglers' Notch he put it plainly: "It is going to be baby steps with Smuggs." At Catamount, Schaefer's February message to skiers said staff had been adding snowmaking capacity.

AIM High replaced the Summit pass and gets more expensive at each deadline

For years the Schaefers sold the Summit pass, which covered unlimited skiing at Catamount and Berkshire East, alongside cheaper night and midweek passes. Most mountains start selling next season's passes around March 1. MassLive reported that this year the owners held off while they worked out a plan, then introduced AIM High in its place. AIM stands for Authentic Independent Mountains.

The price has gone up twice since March. The launch figures come from MassLive's March 2026 report. The later tiers appear on the pass table that Berkshire East and Catamount post for the 2026-27 season.

Since March, the adult AIM High price is up $200, about a third, and the Midweek pass is up $100. Prices exclude tax. Catamount's current page lists only the "Price Until 11/30" column and does not say what comes after it. The pass has gone up at every deadline so far, and the posted table stops at November 30.

Seniors 80 and older and children 6 and under ski free on every pass. Catamount sets the age cutoff by birthday: a child counts as a "tot" if they are 6 or younger on December 1, 2026. A child who turns 7 in mid-November will need a youth pass.

Where the gap between AIM High and Midweek goes

For a Hillsdale household, the size of the AIM High price is less important than the gap between AIM High and the two cheaper passes.

The Midweek Season Pass costs $429 through November 30, which is $370 less than an adult AIM High. It works Monday through Friday, day and night, at both Catamount and Berkshire East, and not on Saturdays or Sundays. It still includes two midweek days each at Burke and Smugglers' Notch, 50% off extra days, and 25% off non-holiday lodging at both Vermont resorts.

The Night Season Pass costs $199, about a quarter of the adult AIM High price. It covers Wednesday and Thursday from 3 to 8 p.m. and Friday and Saturday from 3 to 9 p.m., at both mountains. Catamount says night skiing typically starts in late December and ends in early March. A Night pass bought in November won't be usable for about a month and covers roughly ten weeks of the season.

If you are paying for a single day instead, Catamount uses flexible pricing. Day-ticket prices depend on demand and on how many tickets remain, rise as a date sells, and can sell out. As a result, the busiest Saturdays cost the most for anyone without a pass.

How you split time between weekdays, evenings and weekends decides which pass makes sense. If your only skiing will be after work on a Friday, the $600 difference between the Night pass and an adult AIM High is a lot to pay for unlimited weekends you won't use. For a weekday afternoon session, Cook & Larder sits at 2642 NY-23 in the hamlet. The Berkshire Edge reported in May 2025 that the café and market planned to add made-to-order food, indoor seating and outdoor dining starting that summer.

The Vermont days work like a trip budget

The Bear Den partnership shows up most directly in AIM High's benefits beyond Catamount and Berkshire East. For the 2026-27 season, the pass includes:

• Two days at Burke Mountain and two days at Smugglers' Notch, plus 50% off additional days at both
• Unlimited midweek skiing at Burke in March
• 25% off non-holiday lodging at Burke Mountain Hotel and at Smugglers' Notch
• Additional mountain access and partner benefits to be announced during the season

Those benefits matter most to a household that already plans a Vermont trip. Four included days, half-price extra days and discounted lodging can cover much of a long weekend up north. A household that skis only at Catamount is paying for the unlimited access at home and at Berkshire East, and the Vermont days are a bonus.

Indy Pass visitors book ahead at Catamount

Catamount is on the 2026-27 Indy Pass, which covers more than 300 family-owned and independent resorts. Berkshire East and Catamount were among the first mountains to join the Indy Pass when it launched in 2018.

Catamount requires every Indy visitor to reserve in advance, and it says the rule is there to manage capacity. Reservations can be made up to the day of the visit, but on busy days Indy visitors who arrive without one may not get a ticket. Indy cards don't work at Catamount's RFID gates, so Indy visitors check in at the ticket window or customer service and load the visit onto a Catamount or Berkshire East RFID card. A new card costs $5.

AIM High passholders who want to ski other Indy mountains can add the Indy AddOn Pass. It gives two days at each partner resort and doesn't work at your home mountain, which your season pass already covers. For 2026-27 the AddOn is currently off sale, and Indy Pass has a waitlist in case it returns this fall. Catamount's FAQ confirms no blackout dates for Indy visitors in 2025-2026 only, so check the 2026-27 rule before planning a holiday-week visit around an Indy day.

Before the November 30 column closes

The last posted price runs through November 30, so a few things are worth settling this month.

1. Check birthdays against December 1, 2026. Catamount uses that date to decide whether a child skis free or needs a youth pass.
2. Count your weekend days. If most of your skiing happens Monday through Friday, the Midweek pass costs $370 less than an adult AIM High and still includes the Vermont days.
3. Consider when night skiing starts. The $199 Night pass works for about ten weeks, starting around late December.
4. Decide on a Vermont trip. The Burke and Smugglers' Notch days and the lodging discounts are only worth something if you plan to go north.
5. Ask about kids' programs. Catamount's snow sports school has 2026-27 seasonal programs on sale for children ages 5 to 13, grouped by ability and terrain skills.

Current prices and pass terms are on Catamount's season pass page, and its price table stops at November 30.

If you are weighing a move closer to Catamount, or wondering how a ski-season weekend house fits into your plans, the team at Beach and Bartolo Realtors is glad to talk it through over coffee in Chatham. Contact Us.