The Washington resident and her husband, Robert, first became involved in 1964, 12 years after the WAA's birth.
This month, Mrs. Middlebrook is one of 60 artists whose work is showcased at the gallery as part of its "60 Years/60 Artists" exhibition -- the focal point of a two-month celebration of the association's founding.
"I was a practicing artist when we became weekenders here," said Mrs. Middlebrook, a printmaker. "We were very aware of the art association."
"I became busily active in it in 1976," she reflected. "I had my first show there in 1978 in the middle gallery. Peter Poskas' show was in the front room."
Forty-eight years later, Mrs. Middlebrook is still taking classes at the association and annually awarding the Robert Middlebrook Washington Art Association Scholarship to two graduating seniors from Shepaug Valley High School who are going into the arts -- a scholarship started by her late husband 20 years ago.
She initially became involved in the association through a friend, Margaret Train Samsonoff, and went on to be a board member during the 1970s and 1980s.
For years, her rhubarb pie -- made from rhubarb harvested from her own garden -- was a staple at the associations' fall potluck harvest dinner.
The Washington Art Association was founded in 1952 by Mrs. Samsonoff and 17 other local artists and patrons.
Today, the WAA has grown to some 400 members, said Linda Allard, a board member and chairwoman of the 60th anniversary celebration.
The WAA serves the northwest corner of Connecticut, offering fine art classes and showcasing local and national artists' works.
The goal of the 60th celebration is to "reconnect in a better way" with the community, Ms. Allard said, as well as to revisit the myriad talent highlighted at the WAA over the decades.
"Being active in the community, involving young people in the arts was always important to the Art Association members," she said. "With art programs now not playing a prominent role in the schools, it's important to offer instruction for children and to collaborate with the schools." .
Ms. Allard recalled past WAA shows geared toward a young audience, such as jeans designer Ryan Olivieri's fashion show in the WAA studio, accompanied by music and light show.
"These are the sort of shows to consider if you want to attract a young crowd," she said. "You need to be exposed to art as a youngster to grow culturally and intellectually."
Dimitri Rimsky, 65, a local poet, remembers the early years of the WAA, when his father, painter Feodor Rimsky, one of the initial founders, was involved.
"When they moved one of the current art association buildings from along the (Shepaug) river, I remember my father and Bill Sommerfeld's was the first show held there." Mr. Rimsky recalled.
"The walls were all dark wood and my father and Bill were horrified about hanging their work on them," he said. "In the middle of the night, they snuck in and painted the walls white."
The WAA began as a summer endeavor, with the first exhibition held in July 1952 at the former R. J. Benham drugstore.
In 1954, the association established a home in the former Depot post office.
However, the flood of 1955 destroyed that building, prompting the association to purchase a small brick building on the banks of the Shepaug River and move it to the newly reconstructed Bryan Memorial Plaza, proceeding then to attach it to a group of milk sheds.
"The strength of the association back then was a sense of social activity," Mr. Rimsky recalled. "The Dramalites, a local acting company, was very active at the time and there was a lot of commingling between the groups in creating sets for performances."
Early years of the WAA saw artists, including potters Betty Milton and Mary Minor, engaged in an arts program for children.
It was an involvement revived during the 1990s by Mr. Rimsky and his wife at the time, Benji Getsinger.
Shows of artwork by local students were a regular occurrence in the 1990s, as was an in-schools Art At Recess class, in which area artists gave talks to students about the importance of the arts. An after-school art program was also held.
Architect Peter Talbot, whose father, the sculptor William Talbot, was a WAA founder, remembers Betty Milton and Mary Minor as "being unbelievable with kids."
"The thing I really enjoyed about the association then was the way artists like Betty Milton and Mary Minor had programs for kids that got parents and grandparents involved," Mr. Talbot recalled.
He also opined the social aspect of the WAA in those early years as being a key component of the association.
"They were constantly having gatherings where they would get together at each others' houses and studios," Mr. Talbot said. "My father would have dinners with themes held under a gigantic tent he'd made in his studio, from a parachute he found in an Army-Navy store."
"They were a group of artists and patrons keeping their intellectual interaction with the arts alive even as they lived out here in the hinterland, in the country," he said, with a soft laugh.
In 1983, the gallery space at the WAA was enlarged and a multipurpose studio was added allowing for expanded art instruction. Shows in the 1980s and 1990s included an exhibition of non-illustrative work of cartoonists including Roz Chase.
Shows for the 60th celebration include an ongoing mural, painted over and over again on a wall being installed along the WAA building's plaza side and sidewalk painting on the sidewalks in front of Bryan Memorial Town Hall.
"Our free introduction to art classes during the 60th celebration are designed to take the fear factor out of experimenting with art," Ms. Allard said. "It's going to be a fun couple of months."
For more information about the Washington Art Association's hours and programs, call 860-868-2878 r check www.washingtonartassociation.org.
For a story about 60th anniversary events, see Page S22.For more photos and artwork from the 60th exhibit, check www.newmilfordspectrum.com.