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Petit Blue at an Iconic Chicago Street Festival

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As a small business owner that sells consumer goods, I am constantly exploring sales channels for my products. When I first started the business last year, family members,  friends and neighbors were my very first customers. Early on, I also sold them at a local holiday market at my kids’ school and started my online shop.  This Summer, I decided to expand into that classic Chicago Summer experience, the outdoor neighborhood festivals. Some are big; some are small; but in Chicago, we wait all year for a few months of good food, great music, and excellent local arts/crafts.

I chose the Square Roots Festival, a huge, weekend-long music and vendor event, for my first time selling Petit Blue Goods at these outdoor festivals. It was a new and exciting experience. If you are considering branching out into these Summer markets, I thought I would share with you some tips, tricks, and advice that I learned from this weekend.

Petit Blue sign hung outside of the booth
Petit Blue sign hung on a PVC pipe from Home Depot

Picking a Festival

I live in Chicago, where from the end of May to the end of October, there are street festivals almost every weekend. If you have the budget, and you find that selling at street festivals is a reliable revenue source, you can probably hit most major festivals each Summer. But if you are like me and already have an online store, you should choose a few key festivals to target your best market.

Do your homework. I highly recommend that before applying for a booth, you should attend the festivals first. Check out the product mix and get a good sense of the traffic at the festival. Talk to vendors that are already there and ask their experiences - small-business solidarity! Visit on different days, if you can. And explore which spots in the festival are better for selling merchandise (where do people slow down and not just walk past?). This will help you start narrowing down which market to target next year.

Stay local. Once you have narrowed down the ideal festivals for your products, start by applying for the ones that are closest to where you live. Square Roots is right in my neighborhood and associated with my local Chamber of Commerce, so in addition to getting a chamber-member booth discount (join your local Chamber of Commerce!), I got to meet my local alderman, the head of the Chamber of Commerce, as well as my neighbors. People in your neighborhood are always great potential customers; they are happy to talk to small business owners in their community, and almost everybody wants to support local businesses.

Stay away from food-and-drink specific festivals. Try to stay away from festivals that are mainly focused on food. You can usually tell from the title: burger-fest, rib-fest, taco-fest, etc. Festival-goers at these events are usually more interested in trying all the food than buying retail items from market vendors. 

Picking a Booth

When you did the initial research on your festival, hopefully you also planned out a good place for your booth. I have found the following factors key to finding a great spot for selling:

  • Close to the music stage
  • In the shade
  • Close to, but not in the middle of, the food vendors

Apply early and get your desired location on the street. Festivals normally give out spots on a first-come, first-served basis, so apply early to ensure your perfect location.

Prepping for your Booth

Now that you have reserved your booth, you need to make your booth stand out. I love Pinterest and Instagram for the best inspiration. You don’t need to be really creative, you just need to explore the great, easy ideas online.

For example, since I sell tote bags, I searched Pinterest boards and found an image from a department store hanging their bags on swings. I loved that idea for Petit Blue! So for the background of my tent, I hung my Julia Everywhere totes on two swings that I made from plywood and ropes, and decorated with faux climbing plants from Joann Fabrics. So easy and perfect for my market style!

bag display swing


Find the best look for your booth and you can make it perfect. 

bag display table
totes are displayed on a folding table with two different heights, creating
interesting visual effect.

As you plan, make a checklist of what you need to do; and then make a checklist for the day-of so you don’t forget anything and set-up with less stress.

My Booth Checklist

  • Pop up canopy tent 
  • Extension Cord Reel with integrated outlets, super convenient!
  • 30” x 72” plastic folding table, with two customized covers made from plywood
  • Two IKEA wicker baskets that I borrowed from my daughter’s room. (I used them to pop up two of my bags, making the display more interesting).
  • Two box fans. We hung these on the ceiling of the tent with zip ties, since the weather was extra-hot at the festival. It helped tremendously! 
  • 4 clamp lamp lights for the top of the tent. I had rented electric outlets for my site for the far, so we decided to use plug-in lights. I saw other vendors using this type of lamp that doesn’t require electricity.
  • Use everyday items from home to fill up the tent. I used two blue and white chairs and an ottoman, and an outdoor rug from our deck to put inside the tent and make it more welcoming. I got tons of compliments on those from festival-goers.
  • To attract more people to come to our booth, I made Instagram pop up frame for my brand and hung it inside the tent. People loved taking pictures with it. (To make yours, you can buy an editable pdf file from Etsy, edit it and print it out at Fedex).
  • One of my neighbors tied some balloons together for me so I hung them around the Instagram frame to make it look more festive.

Instagram photo prop with balloons
Instagram photo prop that you can download and print on Etsy.

Getting people to visit your Booth

Display your products out front. Some festival-goers will simply stroll by your booth and barely glance your products. If you place your merchandise at the very front of your tent, or even outside of your tent, you will make people see your items and they should be more likely to stop and check them out.

Give out something free. Provide festival-goers with some cheap, easy, free items that double as marketing tools for your brand. We printed up bookmarks with our company info instead of business cards. Even if people didn’t purchase a tote at the festival, they walked away with something to use and remember us later. 

Ask family and friends to visit your booth. Nothing attracts a crowd like a crowd. It’s a simple fact that people pay attention to and visit booths with heavy traffic. People aren’t as inclined to check out your items if you are just sitting alone in your booth. They feel more comfortable to browse around if there are other people at your booth, and of course, getting people inside your booth to buy something is your ultimate goal.

Your seating situation. Don’t sit at a place that people can see you right away, as they may feel a bit intimidated to come in. Sit where you are less intrusive, and when you see people showing interest, you can follow up. I found that a corner of the tent, or the edge of the tent outside were both good spots.

Finally, don’t forget to put on a friendly face and greet your visitors! 

You and your booth are the first time so many new customers will meet your brand. Make them feel welcome.

After the Festival

Many visitors came to your booth, but didn’t make a purchase... yet! With your free items and business cards, you made sure they would have your business info later, if they decide they need to make that purchase. If you have an Etsy or online store, make sure your web address is extra-clear on your promotional materials. 

bookmark with business info
bookmarks that I used instead of business cards at the festival. I ordered mine from SmartPress.

 It’s also a great idea to provide a festival-specific promotion for people to use later on after the festival. Offer a special coupon code or encourage customers to mention the name of the festival when placing an order later on for a great, special discount.

Most importantly, the festival is your opportunity to meet face-to-face with your potential customers. Even if they don’t buy something that day, get their feedback. Make their opinion matter, and they will feel valued and remember your brand. 

Have you ever set up at a street festival? Let me know in the comments with your tips and ideas!

market vendor nylon bags Petit Blue bags selling at festival small business owner practice street festival travel tote

Comments


  • Great blog for learning about selling your wares at local festivals. I learned some valuable information.

    Brenna Sheridan on
  • Love Petit Blue products! Great blog post with good tips…thanks for sharing!!!

    Carol Fleishman on

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