MEET CRAIG DELLA PENNA
Railroads, history, preservation, sustainability, and real estate have all shaped Craig's career.
CRAIG’S STORY
My career has never followed the traditional path.
Long before entering real estate, I worked throughout the Northeast helping communities convert abandoned railroad corridors into rail trails. I organized local advocacy groups, worked with Rails-to-Trails Conservancy, and became one of the country's most respected voices on rail trail development.
When I became a Realtor in 2003, I brought that expertise into real estate, creating one of the first practices in America focused on homes near rail trails and historic properties.
Today, buyers and sellers benefit from decades of experience, deep local knowledge, and an appreciation for the places that make Northampton such a remarkable place to live.
AUTHOR
OF 5 BOOKS
National Association of REALTORS®
EVERGREEN AWARD
1,200
LECTURES ACROSS 21 STATES & CANADIAN PROVINCES
HGTV
HOME FEATURE
HISTORIC
PRESERVATION AWARD
roads less traveled
CRAIG’S PODCAST
HISTORIC HOME RENOVATION
LIVING THE WORK
My wife & I purchased an 1865 farmhouse just eight feet from what was once an active railroad line.
Over fourteen months, we carefully restored the property while preserving its historic character. The renovation earned a Historic Preservation Award and was later featured on HGTV's Restore America.
Today the home operates as the Sugar Maple Trailside Inn, welcoming guests from around the world—many of whom discover the Pioneer Valley for the first time through our B&B.
WHAT MY CLIENTS ARE SAYING
TESTIMONIALS
THE TEAM
KRISTIN VEVON
Raised in the Lowcountry on Folly Beach, SC, I followed the tide north to NYC for college and a real education in life. In 1982, lured by promises of paradise in the Valley (and a job with the Valley Advocate), I crossed thru the Seven Sisters range and dejavued my way back home. Completely smitten with Western Massachusetts, I stayed and earned my Realtor license in 1994. I spent most of my work life publishing Real Estate Magazines but encouraged by my friend and mentor, Craig Della Penna, we formed The Trailside Team in 2020.
I have bought and sold several homes in local towns but in 1995 I bought part of a 1700's farm and built my forever home with my husband, Scott. Since then I have tried my darndest to fill it with animals, friends, family and familiars! Give me a call if I can help in any way. Advice is free and I have plenty to give.