Sugar Maple Trailside Inn

62 Chestnut Street, Northampton, Massachusetts 01062
Innkeeper(s): Craig and Kathy Della Penna
  • Introduction

    Sugar Maple Trailside Inn, bikes Craig and Kathy Della Penna are both experienced bicycle tourists-who loved staying in bed & breakfasts on those journeys. They enjoyed those stays so much that they decided to open and operate their own B&B.

    Kathy is also a dedicated walker and enjoys our rail-trail both mornings and evenings. She works for the Commonwealth of Massachusetts.

    Craig is a full time Realtor® and he is one of the top realtors in the city and is nationally known for his innovative real estate practice which has been featured in two national and state realtor trade magazines and national press such as The Wall Street Journal, the Boston Globe and even United Airlines in-flight magazine Hemispheres. He is a realtor who ‘gets it’ in terms of smart growth and environmental issues.

    Several B&B guests a year love our area so much that they become real estate clients of Craig, who assists them in the search for a home in the Northampton area.

    For 20 years, he marketed rail freight and operated two of New England’s largest and most successful railroad owned, transloading facilities. From 1998-2004, he worked for Rails-to-Trails Conservancy as their New England Representative, focusing on the transportation policy end of building rail trails.

    He is the author of five books and numerous op-ed pieces/guest editorials on the value of smart growth development, real estate and rail-trails. He has given over 1,200 lectures in 19 states and is one of the country’s most in-demand motivational speakers on these subjects.

  • Insider's Info

    Travelers are always looking for memorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Craig and Kathy Della Penna for sharing their secrets with!
    Why do most travelers stay at your inn?

    50% are here because of Smith College. We are the closest B&B to Smith College—the largest women’s college in the U.S.

    What are you best known for?

    I am best known for developing rail trails throughout the northeast U.S.

    What makes your inn unique?

    Former railroad, now a bike path, is but 8 feet away. We have a tangential tie-in to Sojourner Truth and a host of pre-civil war era abolitionist history.

    What do you love most about your inn?

    The history.

    If someone has never been to your city, what is the #1 reason to come visit?

    This is the #1 Small Arts Town in the U.S. and the #1 place for retirees.

    What’s the best compliment you have ever received about the inn?

    We treated the guests like family and our house felt like home to them.

    What’s the best kept secret about the area?

    The history.

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    There are 10 world-class museums within 15 miles. There is a 25+ mile long bike path that goes right past our house. The most acclaimed downtown in the northeast is our downtown. There are more restaurants here than any other city in the northeast between NYC and Montreal.

    Is there anything within walking distance of your inn?

    We are in a pre-civil war era village center layout with big parks, shops, and safe walkable/bike-able streets.

    What is your favorite restaurant/food in the area?

    There are scores of them. Over 80 in fact.

    Any good area guides/websites that travelers could reference?

    How many rooms does your inn have?

    [Two] 2.

    Do you accept pets?

    We have a Scottish terrier named Ivan and thus we cannot accept pets. Best lodging for pets is at: .

  • About the Inn

    Sugar Maple Trailside Inn, historic photoSugar Maple Trailside Inn is located in Northampton, Massachusetts in the village of Florence.

    The Massachusetts inn is the closest bed and breakfast to Smith College, which is the largest women's college in the U.S.

    The home is a restored 1865 farmhouse style with Italianate characteristics. In 2003, the building was awarded with the City of Northampton's Historic Preservation Award. Restoration of the home was documented and featured on HGTV's "Restore America" series in November 2003. Be sure to view our episode on YouTube.

    Sugar Maple Trailside Inn offers two renovated guests rooms, both which are air-conditioned, furnished with antiques, as well as private bathrooms and views of the rail trail. Your privacy is highly respected.

    A continental breakfast is served in the morning with a great selection of fresh juices, bagels, muffins, scones, yogurts and seasonal fruit. Hot coffee and hearbal tea are available throughout the day.

    Guests are welcome to browse through our library, which houses one of the largest collection of antique railroad maps of the region. Guests can enjoy our 3-season porch or take a bike ride on the rail trail on our Raleigh Retro-Cruiser bikes.

    Visit the Sugar Maple Trailside Inn website for more information about the inn!

  • Layout of Sugar Maple Trailside Inn

    Sugar Maple Trailside Inn, map