Pop-ups, markets, and fairs offer small businesses a low-risk way to test products, build brand awareness, and generate sales. But in-person selling comes with different legal, logistical, and marketing requirements than selling online. 

What counts as a pop-up, market, or fair?

You might not think there’s much difference between a pop-up, market, and fair, but they describe slightly different environments. A pop-up shop is typically a short-term retail space, like a weekend storefront or a temporary kiosk in a mall or shared venue, whereas markets are usually recurring events, like farmers markets or craft markets, that are hosted weekly or monthly. Fairs and festivals tend to be larger, seasonal events tied to a holiday or community celebration.

The format matters because it affects the costs and expectations. A farmers market may have strict food and labeling requirements, while a street fair might prioritize liability insurance and crowd safety. Pop-ups inside existing retail spaces may require fewer city permits but stricter contracts with landlords or hosts. Understanding the event type helps you plan your inventory, staffing, and compliance correctly.

Licenses, permits, and insurance you need to sell in person

Selling in person typically involves more paperwork than selling online, especially when you’re required to collect sales tax and deal with the public. Here’s an overview of what you might need:

  • Business registration: You typically need to be a legally recognized business, like a sole proprietorship, LLC, or corporation.
  • Sales tax permits: You will need to have a sales tax permit or reseller’s certificate to collect and turn over sales tax to the state.
  • Event-specific permits: You may need a vendor permit issued by the event or city, especially if you’re selling food or beverages, which may require approval from the health department.
  • Insurance requirements: You typically need general liability insurance, with the event or venue listed as an additional insured, to cover you if a customer is injured at your booth.
  • Other permits: You may need insurance to cover product liability, especially if you sell physical items that could cause bodily harm.

How to choose the right events for your business

Not every event is a good fit for every product, so start by evaluating the event and the audience. Who is attending this event and why are they there? Some crowds show up purely for entertainment, while others come only to shop. The better your product aligns with the audience, the higher your chances of making sales.

Next, compare the total cost of attending with your potential sales. Booth fees are just the starting point—you also need to factor in travel, lodging, meals, staffing, and inventory costs. You should also consider whether the event helps you acquire repeat customers or whether it’s mostly one-time buyers.

It’s also a good idea to talk to the organizer and ask about their expected attendance numbers, local marketing plan, or backup plan for bad weather. If the organizer is vague on any of these points, you may want to rethink your attendance. Professional organizers also usually provide maps, schedules, and vendor guidelines well in advance.

The value of an event doesn’t end when the booth closes, and collecting email addresses or encouraging people to follow your business on social media helps turn one-time shoppers into repeat customers.

Tips for designing an attractive booth that converts browsers to buyers

Your booth functions as your storefront, so the goal is to make it inviting and easy to navigate once someone approaches. Clear signage with your business name and visible pricing helps customers quickly understand what you sell and whether it fits their budget. Keeping the layout simple also makes your space feel more open, which is important in crowded or narrow aisles.

Once shoppers approach, the physical flow of your booth should encourage them to step closer rather than hesitate. Arrange tables and displays so people can lean in or enter the space without feeling blocked by barriers. Position your checkout area where it’s easy to find, so customers don’t have to ask where to pay when they’re ready to buy.

Lighting also impacts how your products are perceived. Indoor and evening events often require additional lighting to keep displays from looking dull or shadowed. Small clip lights or LED strips can highlight key items and make colors and textures stand out, while also improving how your booth appears in photos that customers may take and share.

Finally, the way you show up behind the table plays a major role in converting interested shoppers into buyers. Standing rather than sitting signals that you’re open to conversation, and a warm, low-pressure greeting is more effective than a scripted pitch. Having a short, natural explanation of what your product does and who it’s for makes it easier to answer questions and guide browsers toward a purchase.

Checklist: What to bring to every pop-up, market, or fair

Here’s a checklist of what to bring to your next pop-up, market, or fair:

Legal and administrative:

  • Business license and permits
  • Sales tax ID
  • Proof of insurance
  • Event confirmation and booth assignment

Booth and display:

  • Table and tablecloth
  • Signage and price lists
  • Product displays or risers
  • Lighting and extension cords

Sales and payments:

  • Card reader and backup
  • Cash and change
  • Receipt system
  • Phone charger or battery pack

Inventory and packaging:

  • Products and backups
  • Bags and packaging
  • Business cards or flyers
  • Promotional materials

Comfort and logistics:

  • Weather protection
  • Water and snacks
  • Hand sanitizer and wipes
  • Notebook or tablet for tracking sales

How to follow up after the event

The value of an event doesn’t end when the booth closes, and collecting email addresses or encouraging people to follow your business on social media helps turn one-time shoppers into repeat customers. QR codes linking to your online store or newsletter make this easier without slowing down the checkout process.

After the event, review what worked and what didn’t. Compare your revenue to the total costs, identify your bestselling products, and note any logistical issues that slowed you down. This information helps you decide which events are worth repeating and how to prepare more efficiently next time.

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.

CO—is committed to helping you start, run and grow your small business. Learn more about the benefits of small business membership in the U.S. Chamber of Commerce, here.

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