During a long weekend last summer a group of friends and I discovered Elephant's Trunk in New Milford Connecticut. We definitely found a holy grail of thrift only an hour from New York City.
In the previously unknown to me Northwest Connecticut--that is also home to a giant man-made lake rumored to have a ghost town at the bottom--Elephant's Trunk has been operating every year since 1976. What makes it especially awesome is it's a flea market of "pickers" who sell to dealers. The pickers are awesome people from across New England, running the gamut of eccentrics who love vintage pyrex to your Red Sox capped dad who likes going to garage and estate sales. That means a lot of the higher priced items in curated vintage stores like those populating in my home of Brooklyn might very well originate here.
One of the benefits to trekking out to New Milford CT, only an hour and so out of New York City though you'll need a car to make it, is the ability to buy from these sellers, many of whom have just picked up fresh vintage wares the days before. All the prices are especially reasonable and naturally, flexible. If you're an actual vintage dealer you can pay extra to arrive at the crack of dawn to buy. But that doesn't mean there isn't a lot of worthy items left after the dealers come.
I've found the two times I've visited the flea that closing is an especially good time. Right before closing a few I found up a vintage globe from between the world wars and a mid century modern magazine rack all right before for much lower than I was expecting to pay.
Tips: Make sure to bring cash! Sellers using a mobile payment card reader are almost non-existent. There are food vendors (and coffee) in trucks and stands on the 55-acre grounds, too. If you're hungry after thrifting, there is a giant diner not too far down the road.
Elephant's Trunk 490 Danbury Road New Milford, CT April to Dec on Sundays from 5:30 to 1:00pm. Parking is free, no dogs, $2 to enter