There’s a learned art in attending a yard sale. There are skills, tricks and tools you must have before successfully venturing out on your own into this cut-throat world of tag sales. Before coming to Fairfield University, I was a passive entity in the game. I watched “Antiques Roadshow” and guessed the price before it was announced. I walked to neighbors’ garage sales when they were selling old books. I even would pop into an estate sale or two if I saw it in the paper. 

But, Fairfield County yard sales are a different breed. On just a singular drive to the grocery store, signs advertising “Tag Sale,” “Yard Sale” and “Estate Sale” will dot the entirety of your route. The houses are large and the items are of higher value; thus, gone are the days with 50 cent books and one dollar rings. 

I’m here to teach you the rules of the game, and to provide you insight into one of my mornings on the hunt for some treasures. Hello, dear readers… and welcome to the world of a yard sale Saturday. 

There are two rules you need to follow before setting out on your own yard sale adventure.

1) Caffeine is necessary. Or, at the very least, you need something to get your brain started up and active for the early morning start. I’m usually out by 8 or 9 a.m., and as a non-early morning lady, I need the extra boost to keep me focused and energized. 

2) Bring good company. A yard sale is, just by its name, fun. But… it’s the company that makes it an event. If you don’t have someone to laugh at the ugly objects you find or the odd people selling them, then it’s just you looking at junk on a rug all alone. 

So, now knowing those rules, let’s debrief my Saturday morning yard sale excursion.

I started, as I recommended to you, with a coffee. 

My sister, the company I chose to fulfill rule two, went an alternative route, opting for some avocado toast to provide her with the sustenance to continue this battle. 

We sat, chatted and caught up, while I went through the yard sale search website. The goal here is to cut down on waste travel time. If you have a good list of those you want to hit, then throw them in your GPS to see which ones are closest to each other, so you can get a lot done in a short amount of time. 

With our breakfast finished, and our minds ready, we headed out to our first destination. 

Burnham Road House

I know it’s not nice to generalize areas, but, after seeing Westport, CT next to the address, I was quite excited to see some expensive things at our first stop. 

The house was a bit odd. It was completely beautiful, all set up on the hill overlooking some type of body of water, but the entire house was empty.

This type of sale is a “staging” set up. Everything is for sale, but it’s all set up to look like nothing was for sale. You know those big long plastic tables usually used for a garage sale? Not in Westport!

A huge glass chandelier hung from the ceiling, while a large snow white couch stretched across the entire room, and there was even an air hockey table. Nothing had a price tag of less than $500. 

This was more of a “what kind of house we’d like to have if we make it big,” experience than an actual estate sale. My sister mumbled an expletive, followed by, “God, this is the nicest house I’ve ever been in.” 

Other than walking around, looking out the windows and gaping at the large swimming pool, there was really nothing there for a young, poor college student to purchase for her tiny Mahan apartment. 

So… off we went to the next building on our list!

Cedar Road House: 

This was absolutely my favorite lot of the day, if not a bit weird to get to. We had little to no directions, and just lucked out in watching someone walk into the backyard. 

Never in my life have I seen a yard sale in the backyard! 

Nonetheless, there we were, and oh, was this place big! It stretched across the entire length of the background. Paintings, a drum kit and a large glass terrarium that looked incredibly Victorian littered the back lawn. 

It had a small pond, with seahorse shaped champagne glasses surrounding it. There was magic within this sale as well, with wooden masks, white wicker furniture and vintage clothes. Still, nothing piqued my interest, so we left empty handed.

Who knows?!:

This wasn’t on the determined list. But, there are a few unsaid rules about yard sales that you only learn when you start attending them yourself. One of which is, no plan is the best plan.

If this means you do a bit of an illegal U-turn while your sister shouts at you just to get to a yard sale you saw with Halloween decorations in the front yard, you do it! This isn’t technically illegal under the laws and regulations of the yard sale code.

If they have Halloween decorations, all is legal. 

So, we made it safe and sound to this surprise yard sale destination. This was the closest to a garage sale that we got that morning. A garage sale is the closest you’ll get to buying something you want, but for which you don’t want to pay full price. 

There were books, particularly ones that are more well-known than the vintage ones you’d pick up at estate sales. Also, I stumbled upon little Halloween lights, with just a few of the batteries dead. 

I recommend garage sales for the novices. They are something low risk to get your feet into the water of this world. 

When asking my sister what she thought of this, she didn’t remember which one I was talking about: “I guess, unforgettable?”

“You mean forgettable?”

“Oh yeah, forgettable!”

Burr Street: 

My sister called this one “drab,” but I quite liked the little miniature poodle that followed the lady with two pairs of glasses on all around the house, circling her legs with its little furless paws. 

This was an estate sale, but it wasn’t a really good one. The best thing about an estate sale is the opportunity to snoop through a house you’d never own. But this number was only the main floor, and so no snooping could be done upstairs or in the basement.

We did a bit of a loop, commented on the house and asked ourselves about the color scheme… and that was about it. 

The only particularly memorable thing was the dog, how endlessly sad. 

Main Street:

I said goodbye to my sister after a full day’s work and dropped her back at school. I’ll be completely honest with you, I was a bit down at this point. We tried to stop at a couple more little sales on our way back, but saw nothing that made us want to stop.

That’s another unsaid rule…your time is valuable. Thus, if nothing is speaking to you from the street, don’t feel bad about driving to the next stop. 

So I went home, only four sales complete, when I received a message from an anonymous Stratford resident and future historical society member, inviting me to a yard sale said to be extraordinary. 

It did live up to the expectations. 

A whole room of just books, and prints and a little snowy village replica with lights snaking around it. 

Sure, the house itself was a bit run down in places. The kitchen floor was torn up while some of the walls looked a bit long forgotten. The understanding that this was once a house of great glory, and that eventually its time would come again, makes me really hope that someone pops in and takes care of it. 

And that, that idea of the past, is why I have such a love for yard and estate sales. The idea of hunting for one small treasure makes all the traveling and coffee money worth it. It is glorious.

Just give it a try one free Saturday morning, and I’m sure you’ll fall in love.

** Edit made on 9/30 to correct the mistake of referring to the anonymous source on Main Street in Stratford as a historical council member, when they are correctly referred to as a future historical society member*

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