Berkshire County — Balderdash Cellars Winery owners Donna and Christian Hanson were just closing up at 8 p.m. on a Friday night in May when Donna was approached by three customers—two brothers and a sister—with an unusual request.
“We were in here washing glasses and one brother came in and said, ‘I hate to ask you this and I’m embarrassed, but we are stranded here,’” she said. The New York and Connecticut visitors were reuniting in the Berkshires because they had just lost a sibling to cancer, Donna Hanson said. Despite finding transportation to the Richmond winery from their Lenox vacation rental, after calling taxi and other ride services, they lacked a viable option to get back, she said.
“No one would come out this way or no one was available to do it,” Donna Hanson said.
Given the alternative of walking back to Lenox in the dark, Donna Hanson jumped in her car and took them back to their lodging, about a 20-minute drive. “It’s been an ongoing issue where people have come up here and asked if there was any Uber or any kind of service to shuttle them around,” Donna Hanson said, adding that the lack of area transportation has been a problem since the venue opened in 2017. “[The siblings] said they loved it here, they loved visiting [the Berkshires], but they said the transportation to get around as a visitor in the area is horrible. If you start before 5 p.m., you can, most likely, get a ride somewhere. After that, you cannot get a ride home.”
Over the past six years and out of necessity, she said she’s given rides to three groups of patrons—including a party of six. “We’re always saying as a country, ‘don’t drink and drive,’” Donna Hanson said. “What are we doing to try to curb that? Owning a winery, especially, makes me nervous.”

An age-old problem
According to 1Berkshire President and CEO Jonathan Butler, transportation in the Berkshires has been problematic for decades. 1Berkshire is the official regional organization that supports economic development and tourism in Berkshire County. “We have drastically underfunded public transportation in rural communities in Massachusetts, the Berkshires certainly being one of them,” Butler said. Although it may be an option during the day, local bus service in the area is limited in its hours and days, with no evening travel offered, according to Butler.
The Berkshire Regional Transit Authority website shows that Bus 15 has the closest stop to Balderdash and that distance isn’t even walkable. “Unfortunately, we end up being dependent upon what the private sector can offer in terms of taxi services, Uber, Lyft, ride-sharing services, and those ultimately tend to be focused more during peak season around large destination areas,” Butler said.
He attributes these travel challenges to “a significant lack of infrastructure” for public transportation. “In other areas where there is more reliably built-out infrastructure, it’s then further supplemented by things like taxicab service and ride-sharing services like Lyft and Uber,” Butler said. “Here, we’re limited to what the market can support.”
Most visitors to the Berkshires don’t get stranded because they “are pretty well-versed on what the transportation infrastructure looks like” and are prepared for it, he said. “But because there isn’t a backbone in our transportation infrastructure, unfortunately, there are incidents like what happened at Balderdash Cellars,” Butler said. “This particular example [of Balderdash Cellars] is a good example of why we need a stronger public commitment to public infrastructure in the Berkshires and in other rural regions that are being underrepresented in Massachusetts.”
Is the answer Uber, Lyft, taxis, or rideshare?
For Donna Hanson, the solution to the transportation issue lies with local elected officials who seek to promote the business area. For Christian Hanson, that answer falls outside of structured transportation models.
“[The area] needs more flexible transportation options that are very unique to the situation, more Ubers, more Lyfts, because it’s not a big city,” he said. “Every experience is different—where people want to go, how far they want to go.”
1Berkshire has advocated for more transportation services in the area but, “it has to be a viable business model for somebody to offer it and those dynamics haven’t worked,” Butler said. A rural destination, the Berkshires has a May to October peak visitor season but that comes to a halt at other times, leaving private transportation services in a financial predicament.
Barbara Zanetti, longtime Executive Director of the Stockbridge Chamber of Commerce, said Uber or Lyft transportation options in the Berkshires are limited. “It’s not something that we have to use 24/7 except for probably during the summer months,” Zanetti said. Adding to the seasonal nature of the influx of tourists, she said the region has a shortage of employees in many commercial areas, “from the kitchen dining room to the store clerk.”
Lenox Chamber of Commerce Executive Director Jenn Nacht recognizes the area’s transportation “has always been a problem, it’s been a problem for years.” She said the town had a few Uber and Lyft drivers operating some years back, but the model wasn’t cost-effective because of the far distances they had to travel between towns to pick up a rider. “I think that where there’s an opportunity, a business usually pops up,” Nacht said. “For us in Lenox, we have so many inns right in town so it’s easy for people once they get [here]—they ride share or find rides or figure out a way up here. It’s a walking town, so it’s not such an issue.”
She suggested that a local Zipcar outlet that provides car rental on demand by the hour or day would help visitors get from town to town.
Taxis may also not be the answer, with the population swelling in the summer and fall months before shrinking when the snow descends. “So if you buy a fleet of cars or taxis and you take that on, what do you do in the winter?” she said. “You have to lay off [employees].”
Katie Smegal has owned Lenox-based Bianco’s Limousine and Livery Service since 2019. The company offers luxury car services and specializes in long-distance transfers, with those trips booked in advance. Occasionally, and if she has availability, she will accommodate short transfers. “People come here expecting Ubers, and 15 minutes before they want to be picked up, they call me frantically because they realize there are no Ubers,” Smegal said. “They have these dinner reservations or they have these weddings they need to get to and now they’re stranded with no option.”
Last summer, Smegal implemented an on-demand, weekend taxi service, 413SayTaxy, to try to help those tourists. It didn’t work out. “The demand for it unfortunately just wasn’t there,” Smegal said. The venture wasn’t cost effective: Having a vehicle set aside for the service, a driver waiting for passengers to call, and paying the extra insurance exceeded the income the business was making, she said. “It’s one of those things that, when people need it, they will call us and they’re outraged the area doesn’t have that service for them but at the same time they don’t understand that 95 percent of the people here have their vehicles,” Smegal said. “So, the demand isn’t consistent enough to make a livable income out of it.”
Uber and Lyft weren’t necessarily created for an environment such as the Berkshires, she said. “In the bigger cities, when you pick somebody up and you drop them off in a different location, chances are there’s going to be someone else in that location who needs a ride back to where you came from,” Smegal said. “So, you are making money in each direction. Here, in the Berkshires, if you are bringing someone to Williamstown from Lenox, the chances of then finding someone in Williamstown who needs a ride back to Lenox are slim to none.” So, half of that drive is done for free, she said, with some Uber and Lyft drivers having branched out on their own to add income.
Jason Canning, who takes fares in the Berkshires full-time, is an Uber driver who runs a private driving company in addition to driving for the rideshare group. His private business picks up where Uber leaves off. “[Uber] has severe limitations; it’s not designed to work in an area like the Berkshires,” Canning said. “So, if a driver is online, they have a range of 25 minutes. If a person being picked up is outside of that 25-minute radius, [the driver] doesn’t even see them as being available.”
Leaving it to the hoteliers
Some larger local lodging properties offer options to take their guests where they want to go.
Canyon Ranch in Lenox offers rides to the town center and can accommodate venues beyond its borders with advanced notice, said the luxury resort’s Dispatcher and Transportation Driver Joe Bilotta.
Miraval Berkshires Resort & Spa shuttles take guests to their destinations, but those trips depend on the availability of drivers, Miraval Communications Host Sara Bouillon said. The service is used for Tanglewood transportation or into town for dinner, she said.
Smaller, independent area venues often don’t offer similar transportation amenities for guests.
Berkshire Flyer
From the expanse of Balderdash’s lawn that overlooks Richmond Pond, patrons can see the Berkshire Flyer pass by directly in front of them. The train is a seasonal pilot program that is in its second season transporting summer and fall weekend vacationers from New York City on Friday afternoon, arriving in Pittsfield at 7:12 p.m. On Sunday afternoon, the train returns to Moynihan Station.

“People on the train have asked, ‘What is that place?’” Donna Hanson said. “[Others] say, ‘Balderdash.’ They pull into Pittsfield. There is no [transportation] service for them.” The Berkshire Flyer website provides information as to transportation options. However, some travel operators have already tried to stake out the Pittsfield train station for fares.
Jim Regan, who owns Pittsfield-based County Rainbow Taxi together with other transportation businesses, said he provided drivers to meet the incoming Berkshire Flyer last year. At first, he provided the service for free, as a promotion, before adding a $35 charge per person to any site in the Berkshires. Regan said he had four riders the whole season, with the train’s travelers mostly being met by friends or family in their private vehicles. This year, he isn’t offering the service. “It’s just not a viable solution,” Regan said, also noting the difficulty in hiring qualified drivers.
Twenty-seven years ago, he began his taxi business with more than 20 vehicles, and now that fleet tallies eight, crediting the downturn to inconsistent call volume. In the evenings, he only keeps two taxis staffed. “Nobody can afford to have vehicles just sitting there, hoping they’ll be used,” Regan said. “If the wheels aren’t rolling, we’re not making any money.”
What’s next?
On May 1, the towns of Great Barrington, Stockbridge, and Egremont embarked on a pilot program to help the area’s transportation shortage for citizens. The TriTown Connector program is a shared ride, on-demand transit service that operates through the three named communities, MicroTransit Program Director Tate Coleman said.
The year-round service is available from 6 a.m. to 9 p.m. on weekdays and 8 a.m. to 8 p.m. on weekends. It will provide trips to anyone for a fare ranging from $2 to $5, depending on the destination, and has nine drivers currently on its staff. The fleet includes four vehicles, including two minibusses. Its funding stems from federal and state grants as well as local matching monies. “I know people who can’t get around or don’t have adequate transportation services,” Coleman said of the impetus for the program.
Similar to Lyft and Uber, the user taps on a smartphone app and can get a ride usually within 30 minutes, he said. A phone option is also available.
Although the project was intended for residents, it can be used by visitors to or from the three coordinating municipalities, Coleman said. “The focus of the project is maybe not necessarily on getting tourists around, although they are welcome to use the service, certainly, but our main focus is our seniors and populations who might not have other means to get around here,” he said.
Already, it has shown great success, Coleman said of the program’s first month of service, and efforts are being made to extend it past its June 30, 2024 deadline.
For now, the project is limited to the three communities named in the program, but Coleman said the possibility remains to expand the program to other Berkshire towns.
Attempts to contact the BRTA and the Southern Berkshires Chamber of Commerce were not returned by press time.