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Sugar Maple Trailside Inn

Sugar Maple Trailside Inn

Sugar Maple Trailside Inn is a bed and breakfast that is located in Northampton, Massachusetts, which is a city in Western MA, along the Connecticut River. The two-story house, which was built in 1865, offers two guestrooms, both located on the second floor, that can be reserved year-round, except for Thanksgiving. The house, and many of the rooms, are decorated with antiques that date back to the 1800s.

In 1868, the railroad was built 8 feet from the house. Railroads are a focal point of the decor and one of the reasons the owners purchased the property. The bed and breakfast owners enjoy sharing the history of the house and the city, and they offer free bikes to people who want to spend time exploring both Northampton Proper and Florence Village, or one of the various biking trails that run adjacent to the house.


The Sugar Maple Trailside Inn has two rooms that are available for reservation: The Cedar Hill Room and The Haydenville Room. The Cedar Hill Room is more spacious and located on the east side of the building with a window that faces Chestnut Street and the 180-year-old Sugar Maple tree. The room comes with a queen-sized bed and a tiled, private bathroom. The Cedar Hill Room also has a genuine Station Master's wall desk from the 1880s that hangs from the wall. The Haydenville Room offers similar amenities as Cedar Hill but is decorated with different decor. The Haydenville Room faces west with a window giving occupants a view of the landscaped backyard. The most notable decoration in this room is the bookcase with a collection of railroad history books that guests are welcome to peruse.

The rooms have antiques that date as far back as the 1800s, many of which coincide with the railways and the stations that once operated in the area. Regardless of which room a guest decides to reserve for their stay, each room has hardwood floors, a television with Xfinity and up to 60 channels, a hairdryer, a heater, air-conditioning, a closet, and a private bathroom with a walk-in shower. Visitors also have access to high-speed Wi-Fi and breakfast.

Breakfast is categorized as an expanded continental-style meal that is served every morning, typically consisting of fresh fruit, baked goods from local bakeries, and granola made by Kathy, the co-owner of the inn. Beverages on offer include coffee, juice, and various types of tea. Breakfast starts at 7:00 AM and goes as late as 9:00 AM on weekdays. On weekends, breakfast begins at 8:00 AM and goes until 10:00 AM.

Along with the two guestrooms, there is a dining room where breakfast is typically eaten and a living room where people can lounge. A trailside patio allows visitors to have a seat outside. Another common area, called the three-season porch, allows guests to get a better view outside regardless of the weather or time of year. The grounds outside have both a front and back yard with gardens. One unique feature about what is growing on the property is the sugar maple tree that resides on the eastern side. The Sugar Maple Tree is over 180 years old and is the namesake for the business.

Sugar Maple Trailside Inn is in Florence's Village Center, which is on the western side of Northampton and known and is an intact Civil War era industrial village. Look Memorial Park is an outdoor grassy area that is less than a mile away from the inn. There are many biking trails in the area due to a large number of parks and mountains and the layout of the town. Mt. Holyoke Range State Park is across the Connecticut River and offers more outdoor recreational activities. Craig notes about the Mt. Holyoke Range that it is one of the only mountain ranges in the United States to run east to west, as opposed to north to south. There are also a variety of restaurants in the area that the owner likes to suggest to his patrons. Eastside Grill is found on the southern side of Northampton and is one of the first restaurants that he recommends. He describes it as a place that serves "New Orleans-style of food in a New England-style restaurant." In the summer, a portion of the street it resides on gets closed to allow for outdoor dining for restaurants on that block. Another recommendation he offers to people is Fitzwilly's Restaurant. Fitzwilly's Restaurant was founded in 1974 and is a combination of a restaurant and bar, offering things from comfort food, such as burgers, to lighter fare, such as traditional salads. Finally, there is Paul and Elizabeth's, which is located inside Thorne's Marketplace. Paul and Elizabeth's is vegan and vegetarian-friendly, while also offering plenty of seafood options.


Craig, the current owner of Sugar Maple Trailside Inn, would like his guests to be amazed by the property, as well as feel comfortable and cozy during their stay. He explains that he enjoys talking to people about the history of the house and the city, especially the historical railroads and the people who influenced life in the town during the 1800s. Biking is another thing that he and Kathy, his wife and co-owner of the inn, enjoy, and he openly offers to lend bikes to people that would like to travel around the city or along the biking trails. "Some things that make people like the area better is how close everything is in the town, all of the bikers, and the quality of safety in the area."

Craig and Kathy have several policies that they ask visitors to abide by while they are staying at Sugar Maple Trailside Inn. The owners have pets of their own, a dog and a cat, so other pets are not allowed at the property. The animals that are not allowed in the guestrooms, in the hope of making those with allergies more comfortable during their stay. The bed and breakfast does not have a quiet time, so people are free to come and go as they please.

The business is open year-round except for Thanksgiving. The busiest time of operation tends to be during graduations at the colleges. He reports that some people have booked out two or even three years in advance for when their child graduates from one of the nearby colleges. A portion of people that come to Sugar Maple Trailside Inn are in Northampton to visit family or friends that are at one of the colleges, like Smith College. Other reasons that people come to the city include seeing the historic rail trails, biking some of the 52 miles of biking trails, eating at restaurants, going to concerts, or taking a brewery tour at one of the various breweries within biking distance of the inn. The property has received several reviews from guests that have stayed there in the past. One person writes, "Great location near rail trail and downtown Florence. The inn owners are friendly and accommodating."


Craig and Kathy purchased the property in 2001. Craig explains that renovations began soon after he bought it and finished in January of 2003. The following month, in February, Sugar Maple Trailside Inn opened to the public. The name of the inn is derived from the 180-year-old sugar maple tree that is still growing in their yard. And the adjacent former RR, now trail.

Craig explains that he was drawn to the lodging industry while traveling for a time while he was writing several books. During this period, he stayed at various bed and breakfasts and learned that he enjoyed the aspects of these accommodations. After returning home from his travels, he and Kathy made the decision to start a B&B of their own. Craig and Kathy live at the inn and have a Scottish terrier called Thelma, whom he frequently refers to as "[our] Scottish terrier-ist," and a cat named Louise. Thelma enjoys people and is known for sitting with guests while they are in the living room. Both pets are friendly toward guests and enjoy greeting newcomers to the property.

When Craig bought the Sugar Maple Trailside Inn, he describes it as being "run-down but not so far gone that it could not be repaired." Craig mentions that he did his best to preserve the history of the home while still making it a comfortable place for people to come and spend time. Many of the rooms portray a few of the historic qualities it has had, though some, like the bathrooms, had to be completely redone and modernized. Antiques of the railroad and other local historic places can be found throughout the house. One recent addition to the house is the solar panels on the roof, which, according to Craig helps power 136% of the current electric needs in the home.

The owner mentions that, in October 2020, a Catalpa tree fell in their yard. He comments on the experience saying, "It missed me by a foot." Due to the absence of the tree, the side yard is more open, and that side of the house has full sun, making the solar array possible.

As well as running the Sugar Maple Trailside Inn, Craig is also a Realtor in the area. He notes that throughout the course of the year, multiple guests who stay at his home decide to relocate to the area, and he enjoys helping them find homes near rail trails.

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62 Chestnut Street
Northampton, Massachusetts 01062
United States


Bed and Breakfast


Craig and Kathy Della Penna

Owned Since
4.63 (46 Reviews)
4.8/5 13 Reviews
4.6/5 17 Reviews
4.5/5 16 Reviews
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