The East Coast’s Greatest Flea Market Is in New Milford, Connecticut

Sort through racks of worn-in denim and piles of antique jewelry and vintage magazines.

New Milford
The Town Green in New Milford, Connecticut. | Fadein/Wikimedia
The Town Green in New Milford, Connecticut. | Fadein/Wikimedia

We like city life because of its proximity to culture, thriving nightlife, and top-notch eats, and we love it despite the abysmal air quality and noisy traffic. But every once in a while, we all crave greener pastures where we can romanticize a quiet existence, full of friendly neighbors, fresh air, and serenity.

A place to fulfill that desire for a slower life is the unpretentious town of New Milford, Connecticut, the home to Elephant’s Trunk, a nearly 50-year-old flea market that’s the antithesis of an overpriced metropolitan thrift store.

Open every Sunday from April through December, upon entering, you’ll notice the lofty size of the market. Taking up the span of a 55-acre field, waltzing in without a game plan can be quite daunting, so here are some pointers to get you started.

Elephant's Trunk Flea Market
Photo courtesy of Elephant's Trunk Flea Market

We recommend starting your sojourn at the far left corner of the market, leisurely making your way through the rows of booths, one by one. You’ll find yourself striking up conversations with the knowledgeable vendors, made up primarily of locals with a genuine interest in their pieces who often make it a family affair by selling alongside their children.

It’s absolutely necessary to at least peruse each stall; even if one doesn’t pique your initial interest, each is rich with treasures you’re unlikely to find anywhere else. Sift through piles of antique jewelry, vintage Life magazines from ’60s, deliciously worn-in leather jackets, and a plethora of unique, funky glassware.

Once you’re fully satiated retail-wise, pick up some nourishment from the line of food trucks for sandwiches served on fresh sourdough along with summer-friendly ice cold lemonade and snowcones. Whether you choose to grab a bite at the market or somewhere else, make sure to pull up a seat at one of the picnic tables and listen to the local bluegrass band.

Drive time:

2 hours from NYC.
2 hours, 45 minutes from Boston.
3 hours, 45 minutes from Philadelphia.
5 hours, 45 minutes from Washington DC.

More things to do in the area:

One of New Milford’s greatest assets is its ties to our country’s rich history. There are a plethora of landmarks listed on the National Register of Historic Places, like the Lover’s Leap Bridge at Lover’s Leap State Park (built in 1895) and the family-run, three century old Hunt Hill Farm (now known as a nonprofit cultural center, The Silo).

To really soak in the woodsy, small town vibes, embark on the New Milford Barn Quilt Trail, a route of 19 hand-painted quilt patterns displayed on various barns and historic buildings throughout the town. The trail leads you from one end of the town to the other; it’s the perfect way to get to know the area and take in its essence. Plus, you’ll most likely see some farm animals along the way; think baby goats, cows, and pigs.

Where to stay in New Milford:

Part of the charm in staying in a place like New Milford is its bounty of independent, local businesses—hence why it’s unlikely you’ll find a chain hotel in the area. Instead, opt for the Homestead Inn, a bed and breakfast that has hosted notable guests like Marilyn Monroe and the Kennedys. Decked out with cozy nooks, picturesque views, and vintage touches, the inn will help you live out all of your Gilmore Girls fantasies.

Where to eat in New Milford:

Located a few miles from Lake Waramug, Upper Crust Cucina serves delectable Northern Italian cuisine in a Tuscan-style farmhouse. The atmosphere alone is enough of a reason to snag a table; the lush greenery and welcoming environment make it feel like you’re visiting a friend’s villa on an ideal summer evening.

Before leaving the inn and hitting the road, pop over to nearby River & Rail Cafe for The Lavender Hive, a spiced honey and lavender infused latte. Take your pick of breakfast sandwiches from their seasonal menu, and get a freshly baked chocolate chip muffin for the road.

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Kelsey Allen is an Associate Editor at Thrillist.