Ann Leary’s Wicked Good Life

Living the Wicked Good Life at the Connecticut Home of Ann and Denis Leary

Published Fall 2012

Interviewing an author poses numerous concerns for a writer. Will they be lofty, formal, or potentially critical of my writing style? Will they be searching for misplaced colons or recognize that participial phrases are not my strong suit? I would soon find out. I was off to meet author Ann Leary.

My apprehension grew as I did preliminary research about Ann, read her books, and listened to her radio show prior to the interview. Ann has authored two books, a memoir, An Innocent, a Broad and a novel, Outtakes from a Marriage, with a third, The Good House, about to be published. She writes a humorous, heartfelt blog at (formerly a wicked good life) and co-hosts a National Public Radio literary radio show, In House. She and her writer co-hosts wittily refer to themselves as Hash Hags, an ironic twist of the Twitter term hashtags. She is the wife of actor Denis Leary and mother of two children, a daughter, 20, and a son, 22. Quite simply, Ann is wickedly funny, creative, and prolific.

She volunteers for two equestrian organizations working with physically and mentally challenged children and regularly volunteers as an EMT for the community of Roxbury, Connecticut.

Somehow Ann has also found time to earn the status of accomplished equestrian — participating in fox hunting, hunter/jumper, eventing, and dressage.

Surprise Guest

When the day of our visit arrived, an unexpected detour prevented our Equestrian Quarterly team from following the precise directions Ann provided to the farm. Had our publisher not had a crack GPS system, we might still be circling the bucolic Connecticut countryside.

Ann greeted us at the top of their secluded drive. But who was the handsome guy with her? Our understanding was we were there to interview and photograph only Ann, take some architectural shots of the house exterior and grounds, and be on our way. We had all done our homework and knew that this particular eye candy wasn’t Denis Leary.

There was a simple explanation. He was a guest of Ann’s FEI dressage trainer Katja Eilers. We couldn’t take our eyes off of him; the alert gaze, the regal stance, a full mane most men would envy. He was, in fact, a magnificent Grand Prix Dressage horse visiting for the day. Our photographer, always quick to recognize a great photo opportunity, put Ann in the frame and started shooting. Pairing Ann’s good looks and spontaneous nature with this regal horse and the results were magic. Ann amusingly referred to her equine model as the “Johnny Depp” of Horses.

For the last year Ann has been working with Katja, who states, “After years of not riding dressage she has been able to pick up right where she left. Ann is extremely athletic and has been able to ride both of my Grand Prix School Masters with ease.”

Feeling Welcome

Spontaneity became the day’s modus operandi. Ann graciously (and unexpectedly) opened her home to us. She immediately disclaimed the Leary décor by quoting a mantra of her mother’s. “We just can’t have nice things.” Ann elaborated, “if you have kids (two) and animals (four dogs) it’s just not feasible.” We saw no evidence of that — quite the contrary. The Leary house is warm, welcoming and sophisticated. An inviting mix of art graces their home, some purchased, some painted by artist friends, and all evidence of the Leary’s educated eye and discriminating taste.

Ann and Denis purchased the 1850s farmhouse in 1997. She described the original condition as “well-loved and well-worn.” Additions were made to the home gradually — typically after completion of one of Denis’s movies or TV shows. Ann shared that, “We named each addition after a project.”

One of the favorite new spaces is the airy sunroom. Surrounded by windows on three sides, it is a room that beckons. We found the light-flooded space a perfect spot to chat with and photograph Ann. The rescued dogs Daphne, Gomer, Holly, and Lulu happily joined us. Ann enjoys writing here when not at her much-cherished “Bed-desk” — an environment she describes as “a king size bed, dogs, papers, computer…heaven.”

In keeping with the light-hearted and relaxed Leary lifestyle there is also a dog room. Situated next to the sunroom, it is outfitted with a doggie door, dog beds, couches, artwork, sconces, and numerous ribbons from horse shows. Truth be told, Ann seemed to enjoy this room just as much as the dogs.

The open flow of the living spaces took us through a spacious living room, sitting room, and an open dining area that led to a comfortable country kitchen. The room is filled with a rich blend of wood surfaces, including the large work island and ceiling. A grand stone fireplace is just one of many throughout the house.

Tranquility and Sports

The outside environment is as charming as the inside. There is a quiet palette of grey stone walls and terraces. Ornamental carriage wheels are strategically positioned at the entrance of the farm, and weathered Adirondack chairs offer tranquil views of the rolling lawns, pond, and woods beyond.

There are two iconic red barns on the property. The converted barn, closest to the house, serves as Denis’s office, where he does most of his writing. Just up the hill from Denis’s office is Ann’s treasured horse barn, where she keeps her much adored horses, Mark and Gabriel. During our visit, the stone wall along Ann’s barn provided endless entertainment for the dogs Holly and Daphne, determined to flush out chipmunks who had taken up residence between the carefully placed stones.

I would be remiss if I didn’t mention the tennis court that also serves as a multi-season hockey rink, where street hockey is played during the warmer months and is flooded and frozen for ice hockey in the winter. With Denis’s strong Boston roots, hockey is a sport taken seriously. The court includes an umpire’s chair, lights for night hockey, and seating for the avid fans that show up.

I asked Ann if Denis enjoys horses. “He loves living with horses,” she said. “He has taken some riding lessons but prefers western style.” She told us he is extremely passionate about all animals and finds any stories about animal abuse unbearable. Even Animal Planet, at times, can be rendered off-limits. The entire family shares Ann’s love of horses, dogs, cats, and visiting critters that inhabit the home and grounds of their idyllic setting.

Why Northwestern Connecticut?

Originally Ann boarded her horses in Roxbury. As she started meeting people in the area and spending more time there, she realized Roxbury would be a great place to raise the kids. The farmhouse, originally planned as a weekend getaway, suddenly became their full-time residence. Ann and Denis also maintain a home in the Tribeca neighborhood of New York City, and recently remodeled a lake house in Connecticut.

This charming farm clearly offers an ideal environment for cultivating creativity, encouraging physical activity, and spending memorable times with family, friends, colleagues, and any lucky dogs that happen to show up.

At the end of the day I realized my apprehension was unfounded. As it turns out, Ann would have neither the inclination nor the time to linger over participial phrases or misplaced colons. She’s much too busy for that.