We just checked the forecast, and it turns out it’s officially flea market weather!
Well, technically speaking, it’s in the high 80s. But that’s the absolute perfect time to head outside and hunt for some treasures, preferably with an iced coffee in hand.
NYC is home to some of the greatest bazaars, flea markets, and thrift stores, and it seems like there’s something new to discover around every corner. But if you’re on the hunt for even more unique finds and a chic weekend escape, we’ve got you covered with something that checks every box on that list.
Just over an hour away sits New England’s largest flea market, and this year it’s back for its 50th anniversary!
Whether you’re a seasoned “upcycler,” a serious antique collector, or just someone who enjoys a great food truck and a bit of Sunday morning magic, “The Trunk” is a New England tradition that truly lives up to the hype.
What to Expect: The Trunk Experience
It all starts long before the sun hits the rolling hills of Litchfield County.
The energy at the Trunk is electric, beginning with a pre-dawn lineup of vendors from across the East Coast. By 7 am, the field is a bustling city of over 500 vendors, featuring an ever-rotating mix of merchandise that captivates all the senses.
Expect a community of “Treasure Hunters” and “Deal Seekers” moving through aisles that feel more like a festival than a market. You’ll find everything from high-end mid-century modern furniture to vintage denim, local farm-fresh produce, and quirky collectibles you didn’t know you needed.
The History: 50 Years of Treasures
The Elephant’s Trunk hasn’t always been the giant it is today.
When it first opened in 1976, a “big day” meant just fifteen vendors set up on the lawn of the 19th-century Victorian house facing Route 7. In those early years, the aisles were whimsically named after New York City streets.
Over the last five decades, this local secret evolved into a national destination, famously serving as a frequent filming location for HGTV’s Flea Market Flip™. Despite its growth, it remains a family-owned staple of the community, maintaining that authentic, “anything goes” spirit that started it all fifty years ago.
What Else to Do in the Area: New Milford & Beyond
New Milford is the gateway to the Litchfield Hills, making it the perfect anchor for a weekend trip.
- Nature Lovers: Head to Lovers Leap State Park for hiking trails and breathtaking views of Lake Zoar and the Housatonic River.
- Chic Shopping: Visit New Milford’s Town Green, one of the longest in Connecticut, lined with charming independent bookstores and local boutiques.
- Sip and Relax: Stop by a local vineyard or craft brewery—like Housatonic River Brewing—to toast to your successful finds.
How to Get There from NYC
The Trunk is surprisingly accessible for a day trip or a weekend getaway:
- By Car: It’s a scenic drive of about 90 minutes from Manhattan via the Hutchinson River Parkway or I-684.
- By Train: Take the Metro-North Danbury Line. From the Danbury station, it is a quick 15-minute rideshare (Uber/Lyft) to the field in New Milford.
Know Before You Go
- Location: 490 Danbury Rd (Rte. 7/202), New Milford, CT 06776
- Entrance: Access via Candlewood Lake Road South.
- General Admission: 7am-2pm
- When: Sundays
- Field Closes: 3:30 pm sharp.
