NORTHAMPTON—BusinessRate recently rated the Sugar Maple Trailside Inn the number one bed and breakfast in Florence for endurance, momentum and the quality of its reviews on Google and Trip Advisor.

In mid-February, owners Craig Della Penna and Kathleen “Kathy” Della Penna received the ranking for the owner-occupied inn at 62 Chestnut St. in Florence, which sits right on the rail trail that passes through the village.

“We’re very pleased,” Craig Della Penna said. “It’s heartwarming really.”

A fierce advocate for rail trails across New England for the past 25 years, Craig Della Penna is the principal of Northeast Greenway Solutions and a Realtor and associate broker at The Murphys Realtors and holds Certified Residential Specialist certification. 

He and his wife bought the Florence property in September 2001 after a meeting in a town near Keene, New Hampshire, where Craig was proposing the conversion of a former railroad into a walking and biking trail. 

“There were always multiple objections from abutters, and they’d always end up with, ‘Besides, you don’t live near one so don’t tell us what to do,’” he said.

That night, Della Penna decided he would live along a trail. He zig-zagged through Florence neighborhoods looking for a house for sale near the trail and found 62 Chestnut St. was available. The Della Penna’s offer was accepted immediately, and they purchased the home, made extensive renovations and opened the inn in February 2003.

Sugar Maple Trailside Inn offers two rooms for guests, both of which have windows that face the trail. A bicycle strung with white bulbs lights up at dusk and becomes a welcoming beacon for arriving guests.

Della Penna said the inn has roughly 350 guests in a year, a quarter of which have a connection to Smith College. Eighty percent of guests use the trail.

After opening as a traditional bed & breakfast, Della Penna said he enjoyed going to trail meetings, where neighbors were alarmed about a proposed new trail. “I’d say, ‘I hear your fear, but I live eight feet from one of the earliest municipally built rail trails in New England—where we operate a bed & breakfast,’” he said. “‘If you are fearful of this change coming to your community, well, we’ll offer up a free weeknight stay for you. It has to be a weeknight, though, because we want you to wake up to the laughter of kids biking to school.’” 

The Sugar Maple Trailside Inn has received other accolades over the years—including the Historic Preservation Award from the city of Northampton and three times as a Valley Advocate Best in the Valley—and it has been featured on HGTV’s “Restore America” and Boston’s WCVB Channel 5’s “Chronicle” twice, and in Yankee Magazine’s 70th anniversary issue.

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