MEET CRAIG DELLA PENNA

Railroads, history, preservation, sustainability, and real estate have all shaped Craig's career.

100+

HISTORIC HOMES SOLD

2003

SERVING NORTHAMPTON SINCE

12k

MONTHLY READERS OF MY NEWSLETTER

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.

A two-story house with solar panels on the roof and green shutters, surrounded by lush trees and a garden, with bicycles parked outside.
Portrait of a middle-aged man with gray hair, wearing a dark green jacket, a white shirt, and a patterned tie, smiling with arms crossed against a white background.

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

Historical map illustrating the Bird's Eye view of Florence, MA from 1879, with an arrow pointing to a house at 62 Chestnut Street. Streets, houses, trees, and railroad tracks are visible in black and white.

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.

Split image showing the entrance to a neighborhood. The top half features a street corner with a stone wall, a crosswalk, and greenery. The bottom half depicts a house with a chimney, surrounded by trees and grass.

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.

A woman with long brown hair smiling, wearing a blue top and a colorful scarf, against a plain background.