GREAT BARRINGTON — Peter Drucker spent the spring semester of his senior year in college driving back and forth between Boston and the Berkshires, preparing to open a clothing store on Main Street. In May 1994, diploma in hand, he flung the doors of Barrington Outfitters open to the public, in what had been the Turner Hardware Store. Drucker started his business with the backing of his family, and was ultimately inspired by his father Bob—who in 1961, at the age of 19, opened the Canaan Army and Navy Store just south of town in Canaan, Conn. The elder Drucker went on to grow a 10- by 10-square-foot venture into a 5,000-square-foot operation over the years that eventually become Bob’s Clothing and Shoes. It was the kind of place his son calls “a ma and pa type store”—and the only place to shop locally (save for driving to the mall).
“There was no such thing as the internet or even mail order back then,” Drucker said, referring to the late ‘80s and early ‘90s. “My dad knew everybody in town, and he knew them by name.” That was the model he and his younger brother Richard, who joined Outfitters three years after its opening, have built upon over the past three decades: a second-generation family business rooted in customer service.
“We overlapped for about 13 years, and it was great working with Dad until he retired,” Drucker said of his now-late father, who closed the Canaan store in 2008. Prior to that the two enterprises shared much of the same merchandise, and afterward Bob, who passed away in 2020, became an honorary full-time employee of Outfitters. “He was here every single day, working the floor,” Drucker said.
The internet was just taking off in ‘94, and the Druckers took great pride in stocking their small store in Great Barrington with clothing and shoes for largely local (and loyal) customers. Their philosophy was simple: “Whatever the consumers wanted, we went out and got,” Drucker said. If someone wanted a particular type of t-shirt, they would find that t-shirt; ditto for shoes and boots.
Beginning around 2000, however, business became tighter. The advent and subsequent explosion of online shopping ultimately forced the retail industry to pivot constantly—if not monthly, then quarterly—to keep pace with the ever-fluctuating trends and lifestyle changes.
What has kept Outfitters afloat through the years?
“We’ve been very fortunate that we have a big enough store to expand into, and our staff is excellent,” said Drucker, citing regular meetings where decisions are made about what brands to move in and out—depending on the numbers. “You have to figure out what’s doing well, what’s not doing well, and move things on from there. And it’s working for us,” he said.
Today, Peter and Richard are 50/50 partners in a business that has grown to specialize in casual clothing and shoes that are, according to its website, “ideal for a weekend in the country…or a camping adventure in the Berkshires” as well as outdoor furniture, which debuted in 2004 with a very limited selection.
Each brother brings his respective expertise to inventory management and buying, which they split into two divisions — with Peter at the helm of apparel and Richard handling the furniture. “This approach really helps when working with family; it allows us to be in the same business but not the same line of sight all the time,” Drucker said. This, coupled with the top-notch customer service on which the Druckers pride themselves, has allowed them to grow exponentially.
“After the pandemic hit, we pivoted to what people wanted, and people wanted outdoor furniture,” Drucker said. They have recently put another 2,000 square feet of the building’s space to retail use and now offer three levels of outdoor furniture at their 289 Main Street location.
Despite the burgeoning business, Drucker has an uncanny ability to be present. “If the furniture business declines in the future, we’ll move it to a different area, and we’ll sell something else,” he says, confident in a model that has worked well for the store. Over the years, the Druckers’ inventory has swelled to reflect popular trends, from memory foam mattresses to stand-up paddle boards and zero-gravity chairs. They think of Outfitters as a mini department store, with customer service as the number one aspect of what they do, and remain cognizant that the products they sell—especially clothing and shoes—can be found anywhere. “We are very price conscious and sell for the lowest price possible,” something made possible because they own the building (and rent does not present an obstacle as is the case for many in the retail industry).
As to the competition from online shopping? “We have no idea if it is or it isn’t affecting us,” Drucker said, acknowledging that everyone—himself included—shops online; it’s the way of the world today. That said, a pair of factors keep Drucker from putting his own inventory online. “We don’t have the volume of stock…and returns are just too devastating for a small family business,” he explained.
The team at Outfitters prides themselves on inventory management, and they keep a tight eye on what people buy (and in which sizes). To that end, their primary goal is to make sure they have the product available for the consumer who walks into the store. “We want to have a presence online, outlining what we carry and how we offer it, as an invitation to please come into our store and receive it,” he underscores. Foot traffic from the Berkshires—not internet sales from California—is invaluable to him.
Drucker is indebted to his consistently high-quality staff. One employee has been on the team for 21 years, and each of three others has been at Outfitters for a decade. Considering the roughly 28 years both Peter and Richard bring to the business, that tallies up to “a combined 100-plus years of knowledge sitting in the store,” he said.
And the customers have come to expect it. Brisk business in recent years led the Druckers to create managerial positions.
General Manager Stacy Twing has day-to-day operations under control, leaving Peter and Richard in the back office—which, for owners accustomed to dealing with their clientele 24/7, has presented a steep learning curve for the brothers. “It’s not what we’re used to, but it’s working,” Drucker said. Assistant Manager Ashley Backhaus is at the helm of the store’s front end and is a wizard when it comes to fitting customers for shoes (especially those with a problem foot). “If she hasn’t fit you for a pair of shoes, you’re missing something,” said Drucker who, at least once a week, offers to help a customer on the floor only to have them demur in favor of Backhaus’ help.
Having grown up in town and graduated from Monument Mountain Regional High School, Drucker has his finger on the proverbial pulse of the community. “One thing that we really like to do is promote nonprofits that help the locals,” he said. Drucker volunteers his time with the high school wrestling team (where he once took to the mat as a Spartan in the late ‘80s), and several of his employees are passionate about raising funds for Blue Rider Stables, a local nonprofit dedicated to therapeutic horseback riding. Clothing and food drives are popular at the store, as were shoe drives (before the pandemic); Drucker estimates Outfitters has sent thousands of pairs of second-hand shoes to developing nations like Honduras over the years.
Now that summer is in full swing, add a trip to Barrington Outfitters to your warm-weather to-do list and stock up on seasonal gear—or even an indoor/outdoor ping-pong table by German-based Kettler.
At one point, Barrington Outfitters was the biggest retailer in the country of non-commercial Kettler furniture. “They called us up one day and said, ‘You have to try a ping-pong table!’” Drucker agreed, and he’s been selling them (practically a trio each week!) ever since. Although shipping, direct from Heidelberg, ceased during the pandemic, they are back in stock for good reason: “People love ‘em!”
This year they switched from fiberglass (aka rigid) paddle boards to more of the portable inflatable ones, making it easier for anyone (no matter how strong) to tote it to the water. “I couldn’t get the regular kind on top of my car so now I just grab the backpack with the inflatable kit and go,” Twing said. “You don’t even have to deflate it all the way between uses.” (The kit, which includes the board, pump, and carry bag, is currently on sale.)
Looking ahead, Drucker sees things as “too fluid” to predict whether a third generation will continue in their grandfather’s—and fathers’—footsteps. “Retail, in general, is a hard thing to manage. In 10 years, who knows what the landscape will be,” said Drucker, whose 30th anniversary in Great Barrington is just around the corner. “We love Great Barrington, and we want to be here, but a third generation? I don’t know.”
