This large-scale market is made for true treasure hunters.

Key Takeaways

Webster Westside Flea Market, or Swap-O-Rama, is Florida’s largest weekly flea, held every Monday on 35 acres in the small town of Webster.
It’s a true picker’s paradise, offering everything from antiques and vintage art to oddities.
Arrive early, bring cash and a cart, dress for the heat, and don’t skip any rows—treasures can turn up anywhere.

As an avid antiquer, lifelong thrifter, and native Floridian, I had heard whispers about Webster Westside Flea Market—Florida’s largest weekly flea. The Swap-O-Rama has been operating for over 50 years every Monday, deep in the Florida countryside in the small town of Webster (population approximately 900). Spread out over a 35-acre swath of covered and uncovered land, the market draws everyone from seasoned pickers to casual, curious browsers. Orlando and Tampa are both approximately an hour's drive away.

Preparing for Webster's Swap-O-Rama

One Monday morning, I finally made the trek from Orlando to see it for myself. I came home with a camera roll full of oddities and a better idea of how to navigate it for future trips. To help strategize my next trip to the flea, I decided to consult an expert who has been attending this market for over twelve years: Kelly Riley of June Taylor Shop. Her wild and shocking Webster finds are always popping up on her antique store’s Instagram page, and she offers insight on tackling this eclectic market.

Here are our top tips for attending Webster Westside Flea Market, and some of Riley’s most astonishing finds of all time.

When To Go to Swap-O-Rama

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Webster’s Swap-O-Rama is open every Monday and some Sundays in the winter months. Dial in your GPS to the “Swap-O-Rama,” Riley says. “There is a large produce market right off the highway that I mistakenly went to the first time.”

The market is open from 7 a.m. to 2 p.m. The earlier you arrive, the fewer crowds and car traffic you’ll have to navigate. You will have to pay for parking, which hovers around $5. Riley suggests arriving at sun-up: “If you go too early, it's very easy to make mistakes buying things in the dark, and many vendors just aren't set up. But if you go too late, you'll miss some great items, and the sellers also start packing up.”

The busiest days are Monday holidays, like Labor Day, MLK Day, and Memorial Day. The summer months are slower, she says, “but not necessarily worse for buying. “There are fewer sellers but also fewer buyers,” She says, but attests there are unique finds at all times of year.

Tips on Shopping Webster's Swap-O-Rama

Don’t Expect a Curated Experience

Unlike markets like Texas’s Round Top and Massachusetts’s Brimfield with their highly curated vendors and tents, Webster’s is a true flea market. Expect to wade through vendors selling everything from toys, to t-shirts, to plants, and even live chickens. Yes, there are antiques and vintage here, but there are a lot of other vendors too, selling all sorts of random oddities that are not home goods. You have to keep your eyes peeled if you want to find treasure. Come expected to overlook sellers peddling bizarre goods that may not be of interest to you.

Bring Cash

You won’t find tap-to-pay or credit card machines at this flea market. Cash is king. “Some [vendors] may accept Venmo or Zelle,” Riley says, “but best not to depend on electronic payment.” There are several ATMs on the property, but for a stress-free experience, arrive with small bills in various denominations.

Don't Skip a Row

Webster’s is huge, and vendors are located beneath open-air covered pavilions, as well as in uncovered dirt lots adjacent to the buildings. “I usually spend most of my time in the field on the west side where items are often thrown on the grass and dirt,” Riley says, “but there are definitely some fantastic dealers in the buildings.”

I was tempted to skip certain pavilions after a quick glance, thinking I didn’t see any furniture or antiques from afar, but Riley says not to get lazy. “I make sure to hit every row because you just never know what you're going to find.”

Go Often for Best Results

The golden rule of thrifting—thrift often—holds true here too. Every Monday at Webster’s brings new items. What thrifters love about this flea market is that items are priced to sell and move. Vendors aren’t being precious about their items—they want to negotiate and sell to you. This means that you won’t attend the same market twice. “You find and learn the vendors that meet your style and prices,” Riley says, “but that took me years to figure out.” Don’t expect items to have price tags. You’ll have to ask the price of a piece, and if necessary, negotiate.

Dress Smartly

“Make sure to dress appropriately,” Riley says. The outdoor market is held year-round, but Florida weather from March through October is hot and humid. “I always bring a large brimmed hat to protect from the sun,” Riley says. And make sure to bring a cart to put all your goodies in. It can be a long walk back and forth to the car.

If you get thirsty (and you should bring water), there are food and snack vendors here too. I loved the Agua Fresca stands with fresh juices in flavors like Cucumber Lime, Hibiscus, and Mango—just $5 for a large Big-Gulp-sized cup.

Look Out for Hugely Discounted Surprises

I didn’t personally purchase anything on this trip. But I did find a 3-foot Venice statue I regret not getting that was priced at $40, and a Giuseppe Prinzi vase priced at $250, retailing online for over $1800.

When I asked Riley about some of her most amazing Webster finds, she could hardly choose. A few that stand out was an art piece she nabbed for $25 and which sold at auction for $800. Riley also said the Swap-O-Rama was where she was introduced to the artwork of Peter Keil, a German artist who studied under Picasso.