Trail Advocacy

This award is given in recognition of successful efforts to influence public policy relating to trail planning, trail protection, trail development, or maintenance.


Massachusetts: Craig Della Penna

Craig Della Penna works tirelessly to promote rail trail development, share information among different groups, and advocate for changes in policy to make rail-trail development easier and faster in Massachusetts.

His consulting firm, Northeast Greenway Solutions, specializes in getting communities to say “YES” to the idea of a rail trail by collaborative processes. Craig brings special skills to public meetings that ease tensions and make for a better public participation process. His newsletter/blog goes out to over 11,000 advocates and decision makers in 12 states.

In his real estate job, Craig specializes in antique houses and residential properties near to rail-trails or other greenways. Recently this unique niche practice was featured in a story in the National Association of Realtors Magazine’s Smart Growth section. Along with his wife Kathleen, he also operates Sugar Maple Trailside Inn, a bed & breakfast located next to southern New England’s first municipally built/operated rail trail. He is the General Manager of Central Highlands Conservancy LLC, [CHC] which preserves former railroad corridor in Massachusetts by buying corridors that are in danger of being lost or sold off to adjacent landowners or inappropriate commercial developers. CHC then protects the corridor by holding it until the local land trust can purchase it through a long-term capital fund-raising campaign.