“We strive to be a place where people can gather, and ideas can grow.”—Stephen Rudy, co-owner of Familiar Trees / RA Gallery
For those seeking a carefully curated selection of books and objets d’art, Familiar Trees /RA Gallery is anything but familiar. The independent bookstore, gallery, and performance space has carved out its own niche in the Berkshires scene.
Proprietor Stephen Rudy has been a collector of unusual printed works for over 40 years. His personal collection helped seed his original shop in Pittsfield. Today, Rudy runs the business at 80 Railroad Street in Great Barrington with his wife, Susana Gilboe, and business partner, Reed Anderson.
When asked why he got into the business, Rudy says, “We saw a need, and we filled it. This area (including upstate New York, Connecticut, the Berkshires, and the Pioneer Valley) is full of artists, writers, and others who make their living in the arts. When we moved here nine years ago, we felt like there should be a place where these creative people could come, exchange ideas, and hopefully learn something new with each visit. We decided to create that space.”
He was also inspired by great bookshops from around the world—pointing to Roman & Williams, which opened in New York, Yvonne Lambert in Paris, and those from the past “like old East Village bookshops that sell avant-garde works.” He also credits his friend and owner of another NYC store called Mastbooks. “I’d been selling to him for years, and he asked me, ‘Why don’t you open your own store?’ So I did.”
Another motivation came from Berkshire locals, who, according to Rudy, “were constantly saying that they wished that they didn’t have to travel to New York City to find anything slightly more esoteric than the usual offerings. We decided to change that.”

Pursuing a passion project
A former product designer, Rudy has long been an aficionado of books. Initially, he and Gilboe funded the business on their own, which he says would not have been possible without his vast collection.
“I have been a book collector since I was in my late teens. My first job was at a used bookstore in Los Angeles. I became obsessed with the business and started to scour the local thrift stores to buy books to consign at the store. I learned a lot about the book business in those years. The love of books stayed with me, and I continued to collect, buy, and sell books and art throughout my life. It made sense that after I started to segue out of my work as a production designer, I should open a shop of my own. After all, I already had the books to stock it!” he says.
The stock at Familiar Trees is 80 percent used, 20 percent new, and a reflection of the owners’ interests. “I look for anything that seems unusual that people won’t find in the area. I always like to find new artists, poets, and writers who I had no idea existed. If I come across something new, I jump on it. We’re very arts-centric, and I like anything slightly more unusual than I’m used to seeing,” he says.
To find new titles, Rudy goes to auctions and estate sales and buys personal collections and libraries. “I’m looking 24 hours a day. At this point, people know what kind of books we do.”
In terms of business operations, Rudy and Gilboe run the bookstore while Reed Anderson manages the gallery. Anderson is an artist whose grandmother was Martha Jackson, an important New York gallerist and the progenitor of op art. Anderson’s father operated a gallery in Buffalo. In addition to running the bookstore, Gilboe is also a costume researcher for the film industry.

Expanding their mission—and their space
From the beginning, Familiar Trees has had two primary objectives: to sell books and promote art.
“Since opening, our mission has grown to include art sales,” Rudy says. “At our previous location about a hundred yards from where our shop is located now, we decided to dedicate one wall to displaying art. This idea grew, and we started to curate shows of work from artists we admired. That wall quickly became way too small!”
One of Familiar Tree’s early shows featured work by Anderson, who had moved to Great Barrington from Brooklyn nine years ago, at the same time as Rudy and Gilboe. “We immediately connected and started to talk about ways that we could collaborate on a larger scale. Those talks quickly turned into the idea that we incorporate an actual four-walled gallery space into the store,” Rudy says. “We decided to partner with Reed and the rest is history. We now are Familiar Trees / RA Gallery. We curate the bookstore, and Reed curates the gallery. It works perfectly.”
With their gallery growing, the team of Rudy, Gilboe, and Anderson soon found itself in need of more space, which coalesced with the end of their original lease.
Besides being larger, “the new location was actually less money so it was a no-brainer,” Rudy admits, adding that the setup was perfect because they were able to put a wall that divided the gallery, which has concrete floors (added by the previous owner) from the wood-floored shop. “Plus, it’s a cool building,” Rudy says.
Beyond books and art, Familiar Trees programs other events including live performances, author readings, and film screenings.
“We want to bring things that are really interesting that other people will find interesting as well. I know Reed feels the same way about art. We also focus on a lot of local artists and try to challenge people intellectually. We strive to be a place where people can gather, and ideas can grow,” Rudy says.
For example, on Saturday, December 9, Familiar Trees screened seven short films by Diane Nerwen, whose works are shown at the Guggenheim, MoMA, and The Tate London. “We want to do [similar programming] once a month. This was our first one,” Rudy says.

Keeping it exciting and staying creative
Like any business, they faced initial challenges, though 2020 was beyond the ordinary. “Our grand opening date was March 20, 2020. So obviously, COVID was an issue. We couldn’t sell any books, and we weren’t eligible for any funding because we couldn’t show a loss,” Rudy says.
Currently, Familiar Trees does not have any employees other than Rudy, Gilboe, and Anderson, who pool their collective expertise to make things happen. They don’t do any traditional advertising, and most of their customers have found them through their roster of events, word of mouth, and social media.
When asked how he defines success, Rudy responds, “We need to make money to keep the space afloat, so it helps when people come in and buy books and art, but ultimately, we define success as being happy and feeling that we are making a difference and bringing something unique to the community.”
Reflecting on their journey, he says, “I don’t think that I would have done anything differently.”
Looking ahead, he says, “The future is really exciting! Brick-and-mortar retail is only successful when people are excited to be in your space. Bringing something new and continuing to stay creative is the challenge but it’s also fun as hell!”
And what of the name Familiar Trees?
“The name is less exciting than it sounds,” Rudy acknowledges. “My wife and I were looking at books at home. We both spotted the book “Familiar Trees” by G.S. Boulger at the exact same time and liked that title for the name of our shop.”
Hot off the shelves…
If you are looking for a one-of-a-kind gift for that discerning someone on your holiday list, here are some of the titles Rudy is excited about; the comments are all his.
“Cosmic Scholar: The Life and Times of Harry Smith,” by John Szwed. If you don’t know about Harry Smith, you should!
“The Invisible Dragon: Essays on Beauty and Other Matters: 30th Anniversary Edition,” by Dave Hickey. A classic and a must-read.
“The Maniac,” by Benjamín Labatut. One of the most interesting new writers around.
“Anna Cassel: The Saga of the Rose,” with text by Kurt Alqvist. If you’re interested in Hilma af Klint, you should learn about Anna Cassel.
“David Wojnorowicz: Dear Jean Pierre”—Just a beautiful book. You have to see it!
Winter hours at Familiar Trees are Thursday through Sunday 12 p.m. to 5 p.m.; closed Monday through Wednesday.
Check their website for upcoming events.
