The Elephant’s Trunk Flea Market: For Those Who Love the Hunt, Not the Hustle

If you’ve ever dreamed of spending a fall morning wandering through a vintage market in the Connecticut countryside, this one’s for you. My route took me along scenic Route 7 to the charming Cornwall Inn, then on to The Elephant’s Trunk Flea Market in New Milford, a favorite stop for treasure hunters across New England. The quiet drive, cozy stay, and colorful market day inspired me to start a new blog series, Antiquing in New England: Hidden Shops and Cozy Stays, where I’ll share hidden shops and cozy stays across this beautiful region. This little trip was the perfect reminder that sometimes it’s not just about what you find, but about slowing down to enjoy the hunt, not the hustle.

About the Series: Antiquing in New England
Starting with this post, I’m launching a new travel series called Antiquing in New England. Each stop will highlight a favorite shop, stay, and find from my adventures throughout New England and beyond. Think cozy inns, hidden antique stores, scenic drives, and those unforgettable vintage treasures that make the journey just as charming as the destination.

An Overnight Stay at the Cornwall Inn, Cornwall Bridge, Connecticut

I decided to spend the night at the Cornwall Inn in Cornwall Bridge, Connecticut, to break up my drive down scenic Route 7 from Vermont. It turned out to be the perfect stop, a quiet, charming inn that feels like stepping back in time. Get Directions

The inn is everything you’d hope for in a Connecticut getaway: cozy, romantic, and full of old New England charm. I stayed in a small second-floor room in the main house with creaky floors and vintage details that made it feel like stepping back in time.

Dinner at the Fife n’ Drum Restaurant in Kent, Connecticut

Just ten minutes down the road in Kent, I grabbed dinner at the Fife n’ Drum Restaurant, where the music was lively, the prime rib was perfectly cooked, and the atmosphere felt straight out of a small-town storybook. After dinner, I headed back to the inn to unwind, ready for an early morning of treasure hunting at the Elephant’s Trunk Flea Market. Get Directions

A Morning at the Elephant’s Trunk Flea Market in New Milford, Connecticut

I grabbed a strong coffee at the Cornwall Inn before heading out, and the drive down scenic Route 7 to New Milford felt like the perfect morning starter, with bright leaves, crisp fall air, and no rush. I pulled into The Elephant’s Trunk Flea Market around 9 a.m., about two hours after the early-bird gate opened (5:30–6:45 a.m.) and one hour after general admission began at 7:00 a.m. That timing worked well, parking was easy, traffic was organized, and the field was relaxed without being too crowded. With food trucks, porta-potties, and wide walking paths, it had all the conveniences of a big market, but felt gentle in pace, just how I prefer.

Where to Start at The Elephant’s Trunk Flea Market

When I arrived, the market stretched across a huge open field, rows and rows of vendor tents as far as you could see. It can feel a little overwhelming at first, so the question becomes: where do you start?

The layout is divided down the center by a main lane, with vendors spread across both sides. I decided to begin on the right and weave my way through each aisle one by one. It kept things simple, helped me see everything without backtracking, and made it easy to bring any purchases back to the car without a long walk.

At the very first table I stopped at, I spotted a small bundle of vintage silver barware spoons for $10. I’d just bought a similar set for myself at Vintage Market Days Vermont the weekend before, and these felt like the perfect little vintage gift idea for the holidays. They were my first (and favorite) find of the morning.

Know Before You Go: The Elephant’s Trunk Flea Market

Before heading out to explore this beloved Connecticut flea market, here’s everything you’ll want to know to make the most of your morning.

Location: 490 Danbury Road, New Milford, Connecticut Get Directions
Season: Sundays, April through December (weather permitting)
Early-Bird Admission: $20 from 5:30–6:45 a.m.
General Admission: $4–$5 beginning at 7:00 a.m.
Parking: On-site and well organized, with traffic guides to help direct cars
Restrooms: Portable toilets are located conveniently upon entering the market
Food: A variety of food trucks offer breakfast sandwiches, coffee, and snacks
Best Time to Visit: Arrive early for the best vintage finds and lighter crowds
Website: The Elephant’s Trunk Flea Market Official Site

Whether you’re a casual browser or a serious vintage hunter, this Connecticut flea market makes for a fun morning stop, especially during the colorful fall foliage season along scenic Route 7.

What I Saw and Found at The Elephant’s Trunk Flea Market

There’s something so energizing about that first walk through a new market, rows of tents stretching across the field, each one filled with something waiting to be discovered. At The Elephant’s Trunk Flea Market, I found myself drawn to the textures and colors of the displays, from stacks of old dishware and barware to handcrafted pieces and rustic furniture. I came away with a few simple treasures that instantly sparked ideas for how I might style them at home for the holidays.

Vintage Silver Bowls with Holiday Charm

The first pieces I found were two medium silver-plated bowls for $5 each, bright, shiny, and full of potential. I immediately pictured them filled with evergreens or tiny plants for simple holiday decor, maybe even styled with pinecones for a cozy coffee table display. I think these two will head back with me to our home in Maine, where they’ll add a touch of sparkle and vintage charm for Christmas.

Blue and Gold Wooden Trays with Vintage Charm

My next find at The Elephant’s Trunk Flea Market came from my favorite booth of the day, a small corner filled with beautiful color and detail. Three painted wooden trays caught my eye right away, each in shades of soft blue with gold accents and delicate brushwork. I decided to bring two of them home at $15 each. They pair perfectly with the silver bowls I picked up earlier and will look so pretty styled for the holidays with a simple red ribbon or a touch of greenery.

The booth itself was a favorite, full of soft blue and pink tones, stacked ironstone, and a mix of silver pieces that gave it a perfectly shabby chic charm. It had so much character and warmth, the kind of space that makes you want to linger and take in every detail.

A Vintage Trunk Turned Bar—Straight Out of Flea Market Flip

One of my favorite booths at The Elephant’s Trunk Flea Market featured a vendor transforming old trunks into one-of-a-kind bars. It instantly reminded me of the HGTV show Flea Market Flip, where shoppers hunt for hidden gems, reimagine them into new pieces, and give them fresh life.

This trunk-turned-bar was a perfect example of that creativity in action. The vendor had kept the classic vintage hardware and structure but added a full interior bar setup inside, shelves, glass storage, and even a place for bottles. It was clever, practical, and completely original, the kind of project that makes flea markets such a fun source of inspiration.

If you’re a fan of Flea Market Flip like I am, you’d have loved this booth. It’s that perfect blend of vintage charm and DIY ingenuity that inspired me to finally visit the Elephant’s Trunk Flea Market on my first true antiquing-in-New-England trip.

The Pieces I Loved but Left Behind

Every flea market has those few pieces that tug at your heart a little, and The Elephant’s Trunk Flea Market was no exception. At one booth, I spotted a hand-painted black chest of drawers that could have doubled as the perfect vintage bar, solid, heavy, and beautifully detailed—nearby sat a rustic little side table with the kind of worn patina that makes a piece feel instantly at home. I thought about bringing them both back, but sometimes you have to trust your instincts and walk away. Even when you love something, not every find is meant to come home, and that’s part of what makes the hunt so fun.

A Blue Trough Too Beautiful to Bring Home

One piece that immediately caught my eye at The Elephant’s Trunk Flea Market was a large, hand-painted blue trough, simple, rustic, and absolutely stunning in color. It had already been sold by the time I spotted it, but I had to stop and admire it anyway. The faded blue finish was pure perfection, and I could picture it styled so many ways; alongside a barn, on a porch filled with firewood, or even as a charming outdoor storage piece. Whoever brought this one home definitely scored.

Final Thoughts on The Elephant’s Trunk Flea Market

I’ve wanted to visit The Elephant’s Trunk Flea Market for years, and I’m glad I finally made the trip. It’s a well-organized market in a beautiful part of Connecticut, surrounded by scenic drives, charming towns, and plenty of antique shops along Route 7. If you’re in the area, especially during fall foliage season, it’s worth stopping by for a morning stroll, a few vintage finds, and the experience of walking one of New England’s most talked-about flea markets.

That said, this isn’t your classic small-town New England market. The vendor mix felt a bit more urban, with several sellers from New York City offering secondhand items, clothing, and collectibles alongside traditional vintage goods. Prices were average rather than bargain-level, and many of the best pieces seemed to sell very early in the morning. Dealers were already shopping by 5 a.m.

If you’re a reseller or love the thrill of the hunt, this could be a fun stop to add to your Connecticut road-trip itinerary. Arrive early, bring cash, and take your time exploring. For me, it was a lovely experience overall: the scenic drive, my stay at the Cornwall Inn, dinner in Kent, and the chance to finally see this iconic market for myself. While it may not be a must-see destination, it’s absolutely worth a visit if you’re nearby and love the hunt, not the hustle.

If you plan to make a weekend of it, there are plenty of charming antique stops and small towns nearby worth exploring along scenic Route 7.

More Vintage Stops Near The Elephant’s Trunk Flea Market

If you’re planning a visit to The Elephant’s Trunk Flea Market in New Milford, Connecticut, be sure to explore a few of the charming nearby towns along scenic Route 7. Each one offers its own unique mix of antique shops, cozy cafés, and small-town New England charm, perfect for turning your flea market trip into a full vintage weekend getaway.

Kent, Connecticut – Just twenty minutes north, Kent is a postcard-perfect New England town filled with art galleries, cafés, and small local shops. It’s also home to the Fife n’ Drum Restaurant, where I stopped for dinner the night before my market visit.

Litchfield, Connecticut – About 30 minutes north, Litchfield’s historic downtown is known for its antique stores, boutique shopping, and scenic streets lined with colonial homes.

Cornwall Bridge – Where I stayed at the Cornwall Inn, a cozy, romantic spot surrounded by countryside views, ideal for an overnight stay before or after the market.

Route 7 Corridor – The drive itself is part of the experience. This scenic stretch through western Connecticut is dotted with antique shops, thrift stores, and small-town treasures waiting to be discovered.

If you love exploring vintage markets as much as I do, here are a few more of my favorite stops across New England, each filled with unique finds, cozy charm, and plenty of inspiration for your next weekend treasure hunt.

Have you ever visited The Elephant’s Trunk Flea Market or another favorite flea market in New England? I’d love to hear about your experience in the comments below. If you enjoy exploring vintage markets and small-town treasures, you might also like my visits to Sage Farm Antiques in New Hampshire, Cabot Mill Antiques in Maine, or my Thrifting with the Gals series for more vintage shopping adventures across New England.

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