Connecting People to Learning, Community, and Place
Hilltown Families is a trusted community resource serving Western Massachusetts since 2005. We help families, educators, and neighbors discover how everyday life can be rich in learning, connection, and joy.
We believe learning happens everywhere—and that by engaging with our communities, we can explore interests, build relationships, and deepen our sense of place. Our content highlights events, local resources, and seasonal opportunities that support meaningful, place-based learning.
Through our free weekly eNewsletter, online calendar, and curated content, we make it easy to find ways to connect and learn across all four counties of Western Massachusetts.
Subscribe to our free eNewsletter to start discovering community-based learning near you.
Our Mission
Hilltown Families’ mission is to support the common good by strengthening a sense of place and promoting self-directed learning through community engagement. This approach, known as community-based education, is inclusive, intergenerational, and rooted in shared values and local culture.
We help families and community members recognize the learning embedded in everyday life—at events, in local resources, and through seasonal traditions. By interpreting the educational and social value of these experiences, we make community-based learning visible and accessible through our online calendar, newsletter, and communication network.
Our method, developed by founder Sienna Wildfield, is a time-tested tool that fosters a culture of intentional learning by linking shared interests and values with opportunities for meaningful engagement.
By making these learning moments explicit, Hilltown Families empowers people of all ages to be self-directed in their education and connected to where they live. Community-based education builds shared understanding, strengthens civic life, and deepens our connection to place.
Hilltown Families was honored with the Essential Agent of Change Award by the Massachusetts Department of Public Health’s Massachusetts Essentials for Childhood initiative, recognizing our role as a leading family-strengthening initiative in the region, promoting “positive parenting through the social norm of community social connectedness.”
What We Believe
At Hilltown Families, we believe:
Learning happens everywhere. Education doesn’t have to be confined to a classroom. Libraries, museums, farms, festivals, trails, and town halls all offer learning opportunities.
Everyone is a learner. Community-based education is for all ages and backgrounds. We support intergenerational learning and self-directed curiosity.
A strong sense of place builds strong communities. When people feel connected to where they live, they’re more likely to care for and contribute to it.
What We Do
Hilltown Families curates and shares community-based learning opportunities throughout Western Massachusetts. We highlight the learning potential in local events, traditions, and resources—then share them through our website, eNewsletter, and social media.
By making these opportunities easy to find and understand, we help families explore their interests, strengthen their connection to place, and learn together in meaningful ways.
Learn More: TEDx Talk by Our Founder
See this TEDx Talk, Supporting Education Through Community Engagement, where Hilltown Families founder, Sienna Wildfield, shares the story behind the vision and mission of Hilltown Families:
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The Heart Behind Hilltown Families
Meet Sienna Wildfield
Sienna Wildfield is the heart and visionary mind behind Hilltown Families.
As its founder and longtime leader, Sienna has shaped the organization into a model for community-based education rooted in curiosity, connection, and place. Her work continues to inspire families, educators, and communities across Western Massachusetts—and beyond.
Sienna Wildfield founded Hilltown Families in 2005 to support families in connecting learning with community-based educational resources, seasonal rhythms, and a strengthened sense of place. Her work has helped shape the region’s understanding of community-based education, offering pathways for self-directed learning rooted in nature, culture, and civic engagement. Her TEDx Talk, “Supporting Education Through Community Engagement,” shares the story behind this vision.
A certified field naturalist and trained mindfulness teacher (MBSR), Sienna brings decades of experience in education, environmental advocacy, and mindfulness to her work. She lives in the foothills of the Berkshire Mountains along the bank of the Westfield River. She is available nationally as a consultant and trainer to those seeking to integrate community-based learning into educational, sustainability, or wellness projects.
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