Tucked in along the beautiful south Connecticut coastline, The Homestead is an amazing combination of luxury without pretentiousness and relaxation with refinement. When we were invited to learn more about this charming boutique bed and breakfast in Madison, Connecticut, we decided it was time for a roadtrip to New England. It turned out to be the relaxing week we’d dreamed about for years.
Easily accessible by car or train, Madison is approximately halfway between New Haven to the west and Old Saybrook to the east. The Homestead is located at 391 Boston Post Road, which is US-1 and also part of the Shoreline Greenway Trail.
Please enter
The welcome mat tells you that Heartman, the owner’s Snorkie (a Schnauzer Yorkie mix), already knows you are here and has probably alerted the innkeeper. The afternoon we arrived, we were met by Ellen, who gave us the tour and ensured we had everything we needed for our stay. After unpacking and settling in, we went back out to see Ellen.
We had a lovely chat, discussing everything we hoped to do, and I made copious notes of places Ellen suggested. One totally unexpected treat was that she mentioned a concert being held that night at the Kate. Acoustic Alchemy was performing, and they’ve been a soft jazz favorite of mine for well over 20 years. Turns out, the venue is named for Kate Hepburn, a Madison resident. A museum below the concert hall has memorabilia of her time in Madison.
Taking the tour
The entry is lovely, with a grand staircase leading upstairs and a hallway into the living and dining rooms.
Passing into the living room, I was struck by the eclectic nature of the room – like being on a TV show set, which I would find out later was exactly the mood that the owner had intended as he decorated the home with entertainment items.
In one corner, a piano, banjo and guitar begged for someone to make them sing, while an antique microphone and an ON-AIR lamp graced the piano top.
An opposite corner awaited the likes of Ernest Hemmingway or some other writer to drop by and feel right at home with an antique typewriter by the window.
The large living room invited guests to sit back in rich leather sofa and recliner chairs or perhaps play a game of backgammon, which was set up and ready in front of the sofa.
Across the room, a fireplace and another pair of upholstered club chairs sit below a beautiful painting of a white birch forest. Wait…a couple of seconds later, the picture frame showed yet another landscape scene. It is actually a large format, hi-def screen displaying a rotating selection of artwork.
Behind the stairs is a dining room, where Ray, the other innkeeper, sets out a sumptuous breakfast each morning. Just like Ellen, Ray has a wealth of knowledge about the local scene and is happy to make recommendations.
Every morning, we enjoyed a rotating selection of delicious guiche, fabulous breads, and/or fresh fruit, all sourced from local businesses. Another digital frame hung over the serving buffet in the dining room and kept us entertained as we enjoyed each morning meal.
On the back two walls of the dining room are a variety of self-serve coffee, expresso, and tea machines, along with an ample supply of coffees and teas to suit anyone’s taste. To-go cups with lids are available if you need to grab a cup and go.
In the corner nearest the living room is a tray with a bottle of Port wine and plenty of glasses if you’d like to relax when you return in the afternoon or evening.
Around the corner is the Sun Room, which should probably be named the Fun Room. It houses a fantastic collection of board games, record albums, and collectibles.
It’s all here, from games to puzzles and antiques to a collection of giraffes. Look and see if you can find the miniature cup that came from the site of the Titanic’s wreckage. I’ll let Ralph Guardiano, the owner, tell you that story when you arrive.
I asked Ellen to check the calendar for some time when Guardiano and I could sit to talk about this outstanding B&B. We were both free Wednesday night, so we sat with coffee, and I was delighted to hear The Homestead’s story.
Rolling back the calendar
In 1958, the original home was built for a doctor, whose exam room was the room where we would spend the week. In the early 80’s, it served two years as the ABC House, run by A Better Chance rehabilitation program with six rooms for disadvantaged inner-city children.
The next owner converted it into an independent living facility with rooms for senior citizens. Through a chance encounter in town, a local shopowner asked Guardiano’s mother if she would look in on his mother who was staying there. That developed into years of daily caring for his mother.
Eventually, the home’s owner couldn’t keep up the mortgage payments and asked Guardiano’s mom if she would be interested in purchasing the house – which she did at age 60. She began to run the entire home herself at that point.
At the time, Guardiano lived in Boston, working with the Boston Red Sox and Bruins Hockey teams. After the birth of his daughter, it seemed like the time to return to Madison and help establish what would become an actual three-generation family business. They expanded the home to serve 16 seniors and he moved in with his young daughter. “It became a family business, and we all worked here,” explains Guardiano. “My daughter grew up here, delivering mail and reading books to the residents.”
Fast forward to 2015, Guardiano took over the operation of the home, intending to continue it as an independent living facility. After his mother retired, however, he needed to hire people to do everything she did. “I ended up hiring seven people to cover all the things she did,” he explained. “She did it so effortlessly – three meals a day, driving people to doctor appointments, doing laundry. It was unbelievable.”
After three or four years, the decision was made to convert the operation into a Bed and Breakfast. “I told my daughter, Nicole,” says Guardiano, “You’re going to be my partner, and we’ll figure this out as we go.”
Meanwhile, Guardiano was still engaged with his creative production company, producing commercials and documentaries for primarily large, well-established hospitality clients. Having worked with Sol Kerzner (developer of Atlantis), even though Guardiano wasn’t involved in the operations of the hotels, he learned that success came from attention to even the smallest detail.
This experience led him to purchase 1000-thread-count Egyptian cotton sheets; memory foam mattresses; shower heads infused with vitamins A, C, and E; and heated bidet seats for every bathroom. Sol’s other lesson was to ‘surprise and delight’ your guests, which The Homestead staff still try to do whenever the situation arises, whether it be an anniversary or other special occasion.
After talking with Ray, Ellen and Guardiano himself, I can see this man has a never-ending capacity to keep asking, “What else can we do to surprise and delight guests?” Here’s a little secret for those planning to book next year – he hopes to add private exterior patios off all the rooms downstairs that don’t already have them.
But I digressed from the tour
Starting with our room, Room 2, located off the living room, it has a private entrance and deck overlooking the treed side yard.
I’d seen pictures on the website, but it looked twice as inviting in person: lovely hardwood floors, a large circular oriental rug in shades of blue, a cathedral ceiling, carefully crafted glossy white wood moldings, and a king-size bed with puffy white covers and king-sized pillows.
A large eight-drawer dresser was built into the wall outside the bathroom door. A full-size coat closet was just outside the bathroom, convenient to both exits.
Yet, around the corner were two more spacious closets. The one with the lovely louvered doors concealed the flat-screen TV across from the foot of the bed, and the other was for more hanging items and concealed a nice mini-refrigerator. The chifforobe also had three large drawers. Heck, we could have brought clothes for a month had we known.
For ambiance, there are realistic-looking candles lit in each bedroom – but they are the battery-operated, safety-conscious-type that look just like the real things.
The beds all have 12″ memory foam mattresses, which is an experience to be had if you’ve never tried them before. All the bed linens are super soft and make getting up a difficult decision.
Each room includes a throwback to the last century – an analog record player and a half dozen vinyl albums with the guest’s favorite tunes. There are dozens more albums to pick from in the sunroom. “In this high-speed digital world that makes us all exhausted,” explains Guardiano, “once you put that record on, it takes you back, the stress peels away, and you disconnect from your digital world for a while.”
On the flip side (pun intended), each room has two multi-use outlets for all the digital tools we can’t leave home without. In our room, one was on the desk, and another was on the bedside table. Well thought out, the three standard receptacles will take either American-style 2 or 3-prong plugs, or European-style plugs. There are also spaces to attach six USB-A charging cords.
When asked where he gets his inspiration, Guardiano credits it to having traveled the world and visited some of the most fabulous places, where he would always take pictures – either of items done exceptionally well or exceptionally poorly. That’s where the idea came from for the two chargers in each room.
As another invitation to relax and recharge, there was an adorable chess board with live edge wood top and a drawer full of wooden chessmen.
In the bath, every essential is there for your comfort. The shower has an innovative vitamin-infused filter head and a hand wand for rinsing. I’ve never seen a wand like this before, but it worked wonderfully. Large pump bottles of lovely body wash, shampoo and conditioner were wall-mounted in the shower.
Each bath also features a heated bidet seat. I first experienced them in Taiwan; now, I have two at home. That’s something I really miss when I travel – but not here.
The magnifying mirror (10X, my guess) was one of my favorites, if you really want to see if you got a close shave.
Also, next to the hair dryer under the sink, the first aid kit was something I’ve never seen anywhere else I’ve traveled. They certainly do try to anticipate any possible need a guest might have.
Guardiano is blessed in that he credits Madison with numerous great craftsmen he calls on regularly as he keeps updating his rooms. We benefitted from the one who is a tilelayer by trade but asked if he could try hand painting a design in one of the baths. What he ended up creating was an ever-so-lovely spray of birds and branches extending around the bathroom mirror. So cute.
Another darling touch was the bird painting and antique clothes hook just outside the shower. Handy, yes, but a perfect companion to the birds on the opposite wall. It’s ‘surprise and delight’ everywhere you look, just as Guardiano mentioned.
More rooms – more fun
During midweek, when a few of the rooms on the first floor were empty, I got to peek in and grab some photos. Each room is unique and painted in a different color. Guardiano credits his niece (a professional designer) with creating the attractive color palette used throughout.
Most rooms have hardwood floors, especially those that are dog-friendly. Many have exterior doors and private sitting areas in the wooded exterior that wrap around The Homestead.
Each room is unique in its layout and furnishings. You won’t find any mass-produced ‘Hilton-standard’ furnishings here. Following is a quick photo tour of a few rooms I saw.
Outside
There are numerous sitting areas around The Homestead, but two common area seating areas have gas fire tables where guests can make their own s’mores in a cone.
Spotted around the yard are a series of “holes’ for disc golf – using a smaller version of a Frisbee instead of a golf ball.
If you arrive in an electric vehicle, you’ll be happy to find electric chargers in the parking area.
There is also a supply of beach bikes if you’d like to bike to the beach or downtown.
Neighborhood
We arrived in October, well after the summer season, but swimming and water sports are a big draw on the southern Connecticut coast.
Just across the highway is the Surf Club, with miles of superb sand beach. It’s for residents only, but you can get a day pass from The Homestead.
Downtown Madison has a number of places you won’t want to miss. If you love tea, you must stop at Savvy Tea Gourmet, where Phil and Judy have a huge collection of teas from around the world and a world of knowledge about each. They also do virtual tea tastings via webinars.
Be sure to ask about Ralph’s blend – it’s named after Ralph Guardiano, and it’s heart-healthy.
If reading is your cup of tea, a must-see is RJ Julia Booksellers, with two floors of books and more. They even have a coffee shop on the first floor where you can read your latest purchase. Keep your eyes open for famous authors who frequently do readings there.
Looking to exercise? Just a few minutes away is the Hammonasset Beach State Park with trails, a nature center, a ½ mile boardwalk, 2-1/2 miles of beach, and a mile-long bike path.
For entertainment, check who is performing at the Kate or the Goodspeed Opera House. Both are highly recommended.
There is a variety of dining choices. I’d talk with the staff and tell them what you are looking for. In addition to those in town, about a half-hour’s drive will get you to many more in nearby Essex, Mystic, Old Saybrook, New Haven or East Haddam.
Wrap up
I can’t recommend The Homestead enough, in case you haven’t gotten the message already. The staff is always available and willing to offer any assistance requested, but they are also unobtrusive during the day, so you can feel like the house is your own if you just want to quietly read a book by the fireplace. We had such a wonderful, relaxed time there; it couldn’t have been more pleasant. And that’s exactly how everyone wants their guests to feel, from the staff to the owner.
“I went to some of the best schools for television and production, and I’ve had an amazing career working with some of the best celebrities, but if I had to do it over, I’d do hospitality,” posits Guardiano. “There’s just something about welcoming people in your own home. I’m having a blast!”
The Homestead
391 Boston Post Road
Madison, CT 06443
203-245-0212
https://www.homesteadmadison.com/
Doug Bardwell
Writer – photographer – drone pilot
Doug writes about architecture, construction, technology and travel. His travel has taken him to 40+ countries, and his articles and photography have been published around the world. There’s nothing he likes better than discovering new photogenic locations and destinations.
