Naptown Flea Is Bringing Vintage Finds to Downtown Annapolis

Stalls with racks of thrifted clothes, boxes full of handmade jewelry, and tables covered in vintage décor. At Naptown Flea in downtown Annapolis, you can find local resellers and makers packing the street to sell their wares. This pop-up market brings energy that is exciting while still being welcoming and friendly. And it’s the perfect excuse to spend some cash on your next favorite thing! 

What Is Naptown Flea?

Declan Levery, creator of Naptown Flea, knew Annapolis had an opportunity. “Before Naptown Flea, I used to sell vintage clothing myself. I would do events all over the DMV, and I saw the community that a lot of these vintage markets have created. I saw a need for Annapolis to have this sense of community, a different demographic, and I just ran with it.”

He was clearly onto something, because the town has embraced the event and helped make each one special.

“Annapolis is honestly a great place for any event, just the way the community and other small businesses buy into events is awesome. But when it came to Naptown Flea, we just got so much support since the beginning and it made me want to really invest my time and effort to make Naptown Flea great.”

Held about once a month, this market is a must-see event. There’s not only shopping, but also live music, food, drinks, and even flash tattoos. They’ve had events on Market Place, Maryland Avenue, and at GameOn Bar & Arcade on West Street. Plus, they’ve teamed up with HERE. A Pop-Up Shop to sell at the store’s most recent location.

Know Before You Go

The next event is a collaboration with Lucky Girl Market, which is another vintage and makers market you can find in D.C., Maryland, Virginia, and Pennsylvania. This means the market will be bigger and better than ever! You can visit Naptown Flea’s Instagram or Facebook for info about all their vendors.

When: Sunday, September 13, 10 AM to 5 PM.
Where: Maryland Avenue
Cost: Free!
Parking: Calvert Street Garage is free all day on the weekends. On Sundays, other garages are free if you arrive after 6 AM and leave before 2 PM. 

Here are my tips for getting the most out of your market day:

• Make a list and a budget. Any thrift store or flea market gets overwhelming when you don’t have a goal. Try to think of what you want or need. Someone’s birthday coming up? Want a piece for a Halloween costume? Or do you want to add to your everyday ensemble? You might not find exactly what you want, but it makes the experience more manageable. 
• Bring cash. Most sellers take payment in many ways, including Zelle, Cash App, and Venmo. But those may come with a few extra dollars of fees. Cash is always welcome!
• Bring a tape measure. Don’t be like me, looking at a skirt in a thrift store and taking “Size 14” for granted. It was not my size 14, I’ll tell you that for free. Luckily, vendors will be happy to help you find something that is the right fit.
• Bring a bag (or two, or three). Many sellers may have shopping bags, but it’s always a safe bet to bring a tote.
• Remember and promote your sellers. Unfortunately, I have walked away from a booth with something I love, only to realize later that I don’t have their name. (And because I paid cash, I don’t have their business handle, either!) Be sure to grab a business card or ask for their social media. Then give them a shout-out online. Share the love!

Bring the Kiddos

If you’re thinking, “That sounds great, but what about little ones?” I understand! So here are my top tips for you to have the best time with your children:

• Try a scavenger hunt. Create a list or a bingo card with some fun finds. They can look for certain colors, animals, vehicles, and other designs. There are plenty of places to look, including on clothing, home décor items, or anywhere on Maryland Avenue!
• Find some nostalgia stock. “Vintage” means anything that is at least 20 years old. I hate to break it to you, but that includes anything older than 2006. However, many vendors love finding and reselling merch and toys from the 1990s and 2000s. Your kids might love some Hello Kitty or Care Bears.
• Dance mode! Musicians from the Annapolis Songwriters Festival will serenade attendees throughout the day. You and your family can be just like the Heelers and launch into Dance Mode.
• Grab a bite. If you’ve always wanted to try Ekiben in Baltimore, but without the drive, now you can! They will have a food truck with some of their most popular options. However, if your kids are picky eaters, you won’t have to go much farther for them. Maybe head down to Dock Street and Market Space to get some treats and ice cream.
• Spend the rest of the day downtown. When you’re all shopped out, you can go to one of Historic Annapolis’ properties, such as the William Paca House and Garden. You can also feed the ducks at City Dock’s Quack Snack Station, take a boat tour, or visit the Naval Academy’s visitor center. 

More to Come

If you can’t make it this Sunday, it won’t be long until the next market. Levery has plans to keep it going and growing.

“With every flea market, there’s always a new lesson. Early on my biggest one was more space, I needed more shoppers to be able to walk around comfortably. Recently, it’s been: How can we make this market more accessible for everyone and make this mutually beneficial for us, our vendors, and everyone in Annapolis. There’s always something we can improve on, so I’m excited to only get better!”

This will continue to be a great event for vendors and shoppers. “I envision Naptown Flea to be a staple event in Annapolis. I want every event we throw to be special and unique. I also want to continue to support small businesses in Annapolis and around Maryland. I think a lot of people can use Naptown Flea as a stepping stone to something bigger.”

You can support local businesses, get yourself some new swag, and make some memories in Annapolis. Naptown Flea is a community event that you and your family will want to come back to again and again.