WHPA Strategic Plan, 2021-2025

Read our full Strategic Plan as a PDF here:
WHPA Strategic Plan 2020-2025


Our Mission: In order to foster habitat conservation, watershed integrity, low-impact outdoor recreation, education, and the enduring connection of people to the natural world, we acquire and provide access to lands along the Windmill Hill Ridgeline and nearby areas.


The long-term vision of the Windmill Hill Pinnacle Association is to have an interconnected network of natural and wilderness areas collectively stewarded by multiple conservation organizations connecting people to the land through education and recreation and which is sustainably balanced with the preservation of natural and wild habitat.

In order to further the mission and long-term vision of the Windmill Hill Pinnacle Association, we will focus on three central areas for the next five years: Stewardship, Succession, and Scale. This Strategic Plan will be implemented under the leadership of relevant committees and evaluated by the benchmarks listed.

This strategic plan incorporates feedback and ideas from our members, partners, funders, and stakeholders who were interviewed for our strategic planning process. Over 150 community members responded to our public survey.


By law and tradition, land trust protections are designed to be perpetual, which means forever. Good stewardship is an implicit promise we make to funders, donors, taxpayers, trail users, etc. To date, we have fulfilled that promise, but how will we meet it in 20 years? How about 50 years?

Faced with this challenge, some land trusts are beginning to shift their focus, their fundraising, and their messaging from acquisition to stewardship. Given external threats, like climate change and invasive species, land stewardship is becoming more complex and more urgent.

  • Prioritize ongoing stewardship and monitoring, including trail upkeep, structure maintenance, and invasive species management.
  • Continue to build the endowment to ensure perpetual protection and maintenance of properties, trails, and structures.
  • Emphasize climate mitigation in stewardship activities.


Action Steps:

  • Support current volunteers. Recruit and train new ones as available.
  • To fund the endowment, emphasize a planned giving program focusing on bequests and real estate/trade lands.
  • Increase opportunities to collaborate with school programs.


We continue our commitment to recruit, develop, and empower the next generation of leadership for the Pinnacle, while deepening and broadening community involvement in our work.

Vermont’s population is one of the oldest in the nation. This creates a demographic challenge for nonprofits: How do you identify and recruit younger leaders?

Furthermore, successful conservation depends on commitment from the broader community, as we ask them for volunteer hours, financial support, and advocacy for land protection. People won’t protect what they don’t love—and they won’t love the land unless they experience it. Hence the need for community conservation: helping people engage with the forest, trails, wildlife, and all the benefits of being outdoors. When we do this well, we broaden our base of future leaders and donors.


  • Design proactive leadership transitions; identify and prepare in advance.
  • Deepen community programs to bring more people to our properties, while also balancing the impacts of increased usage.


Action Steps:

  • Facilitate a workshop on board succession planning.
  • Update bylaws to be flexible and adaptive, including remote meetings and mail-in voting.
  • Create a “volunteer leadership ladder” so people who show promise and commitment can take on more responsibility. Include ad-hoc volunteers in committees to expand the depth of talent and experience.
  • Enrich and expand community outreach to new audiences by improving the website, using social media more effectively, etc.
  • Establish a digital archive for WHPA records.


To ensure the perpetual protection and enjoyment of the land we have already conserved (and might conserve in the future), we will work towards identifying the right scale—geographically and organizationally—for our work.

The WHPA has protected 2,100 acres (2,700 acres as of May 2021), created and maintained miles of trails, and provides a variety of community programs. However, funders and other stakeholders have expressed concerns about the long-term viability of a volunteer-based structure. A changing economy impacts how people volunteer and how much time they have available. Given this reality, we may need to adapt our model.

At the same time, how do we prioritize stewardship of existing properties versus acquiring more properties and adding more trail miles? How big do we want to be, geographically speaking? With the understanding that new acquisitions require perpetual oversight, what’s a reasonable goal?

  • Expand conserved areas as opportunities arise, with the understanding that not all properties require recreational access; nor do they need to be owned or managed by the Pinnacle.
  • Collaborate with adjoining property owners on land conservation projects.
  • Explore alternative leadership models, focusing on implementation on a trial basis.


Action Steps:

  • Review and re-evaluate our criteria list/ranking system for potential acquisitions.
  • Create a “ready fund” or “opportunity fund”—available cash for land deals.
  • Review and re-evaluate board and volunteer capacity.
  • Implement new leadership models on a trial, exploratory basis.
Child hugging a tree at the Pinnacle

Child hugging a tree at the Pinnacle.

Nailing up the “Entering Pinnacle Association Land” sign at the grand-opening celebration of the Athens Dome acquisition at the Lake Property in Grafton

Nailing up the “Entering Pinnacle Association Land” sign at the grand-opening celebration of the Athens Dome acquisition at the Lake Property in Grafton.

Fog and fall colors

Fog and fall colors. Photo: Ed Aplin