I just got back from my third visit to the MIT Flea Market. As usual, I spent a few hundred dollars US and filled up most of my car. Located in Boston, the flea market is about a 6 hours drive away from me. I generally try to bring a friend and I stay the whole weekend.
What is it?
The MIT Flea Market is a huge flea market, primarily focused on computers, electronics, and ham radio. It runs every month, on the third Sunday of the month, from April to October. It spans 5 floors of a parking garage and has extremely good prices, for the most-part. I've seen plenty of retrocomputers, modern computers, antennas, transceivers, oscilloscopes, spectrum analyzers, as well as plenty of random doodads. Aside from all the stuff, there's a lot of cool people there, and plenty of opportunity to have rich conversations about niche interests.
The only exception to the amazing prices is on ham radio transceivers. They're not a bad deal, generally, just more inline with what I see at other US hamfests. Actually, the prices are a bit better in Canada, as far as I can tell - similar dollar numbers, but in our nearly-worthless CAD.
Things I've purchased
To give an example of what kind of things are at the flea market, here are a few things I've purchased. Prices were generally extremely reasonable.
Retrocomputers - TI-99/4A, Osborne, TRS-80 model 100
SFF PCs - 4th gen i5s; I use them as cheaper (and more powerful) Raspberry Pis
Desktops and servers
Rack equipment - shelves, switches, etc.
HBAs - I normally see them for just a few dollars a piece
Getting around Boston
Boston is a terrible city to drive around in. The drivers are okay-ish, but the layout of the city is extremely confusing. Even with GPS it was a struggle, and I got lost a few times. I even had a friend helping me navigate! It seems that approaching from the west side of the city helps a little. I did that on a previous visit and it went more smoothly - though it was definitely still stressful.
In contrast, the public transit in Boston is very good. I often stay in Providence, Rhode Island, about an hour south, and can get a weekend train pass for $11 USD. A 24 hour bus/subway pass is only $10 USD on top of that. I think it's some of the best public transit I've experienced.
Unfortunately, you're really not going to want to lug a bunch of stuff onto the metro, so I highly recommend driving to the flea market. If you don't have a strong mental fortitude, try to trick your friend into driving you! Honestly, try to get someone else to drive regardless. It's not a pleasant experience!
Parking
Even though the flea market is in a parking garage, it's parking for sellers only. I even asked if I could pay the seller fee as a buyer to park there, but they said no. It makes sense - don't want to fill the garage up with buyers!
My preferred option is to park in buyer's parking. It's located a block or two from the parking garage. It fills up fast though - arrive early; no later than 8:45 and there should be space for you. Every time I went to my car to drop off a load, I'd always have at least one person asking "are you leaving?".
If the parking lot fills up, hope is not lost! Street parking is free on Sundays in Boston (or at least, in that area) - it lines up perfectly with the flea market. You'll probably need to park further away, which is the main reason I avoid it.
Also, bring a cart. It helps massively with getting things around the garage, as well as to your car. You might be able to do without one, but remember that every trip to the car is valuable time that other people are using to buy the cool stuff! My first flea market I didn't bring one, and I had to pass on a lot of awesome things that I wouldn't be able to get back to my vehicle. Oh well - at least it left more room in my house for the next flea market!
Strategy
This is how I generally do things at the flea market. There may be better ways but it works well for me.
First of all, make a list! I get a lot of skepticism when I bring people. "I only have 3 things I want; I can surely remember them all". But by the end of the day, they all have one, or they all say they wish they made one. Basically, you don't want to waste any brainpower by needing to keep track of your list, and no matter how short your list is, you'll always forget something. Before you leave, you can do a once-over and confirm you got everything that you could find.
When the flea market opens, I normally do a quick pass, at a fairly brisk walking pace. Generally my goal is to just get a sense of what's available. If I see any really good deals, or anything that matches up with my list, I'll haggle/buy on the spot. After the quick pass, I might do another one or two, before moving onto much slower, more intentional passes. If you're there with another person, I recommend doing the quick passes separately at a minimum. You'll both be interested in different things and you'll tend to slow each other down.
On the subject of haggling - don't be afraid to do it! I think it might be my favourite part of the flea market. It's a very low-stakes environment - worst case, you might offend someone or not get something you want. But it's a great skill to have, and the vast majority of sellers are very receptive to it. If you see someone with a few things you want, try offering a price for them all!
Other hamfests
There are other hamfests in the area around the time of some MIT Flea Markets. This is complete speculation on my part, but I believe this may affect turnout at the MIT Flea Market. If you're travelling relatively far (like I am!) these may affect whether you want to go or not. Remember, there are 6 per year, so if you're only going to one, it would be good to optimize which one you go to!
Dayton Hamvention
Dayton Hamvention is one of the largest hamfests in the world. It takes place annually. This year, it happens on the same weekend as the MIT Flea Market. It runs from Friday to Sunday in Xenia, Ohio. It's about 12 hours away from Boston by car. While it would technically be possible to go to both, you'd need to miss a significant portion of Dayton Hamvention. I think that most people would choose one or the other. This may cause lower turnout at the MIT Flea Market.
NEAR-Fest
NEAR-Fest is one of the largest hamfests in the area. It's significantly bigger than the MIT Flea Market. However, it's only a few hours away, and it only takes place on Friday and Saturday. Therefore, it seems to me that many people would go to both - I have in the past! I would expect a larger-than-normal turnout when these line up. NEAR-Fest takes place every 6 months, and if it lines up with the MIT Flea Market, it'll generally happen in April and October.
If you're reading this in the future, it would be good to verify the dates of these flea markets to see if they land on an MIT Flea Market weekend or not.
Overall, if this seems like something that could interest you, I highly recommend making the drive to Boston. It's a great time, with a great atmosphere. After going to a few you may start to recognize the regulars, and they may start to recognize you too!