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Fairs and conventions can be a great way to connect with new people and sell your artwork, but they can also be expensive. There’s the cost of your booth itself, along with travel expenses and time off of your day job (if you have one). Try to sell first at events close to your home, until you have a good grasp on what you need to do to succeed at a convention. Many conventions start booking their booths nearly a year in advance; you’ll want to stay on top of deadlines for your chosen events, and apply as early as possible. Most conventions have a set application, including a portfolio and an artist’s statement--this will help the organizers determine if you’re a good fit in genre and style. However, it’s just as important to know if the convention is a good fit for you. Before you apply, find out the answers to some of these important questions.  How much space is each booth allowed? Is a chair included? Will there be an outlet nearby? Is the space accessible (especially if you have any mobility considerations)? When you go to a fair or convention, you’re not just there to hang out: you’re there to promote your artwork and your brand. Be kind to everyone, from guests to fellow artists to staff, don’t let your art spill over onto other people’s tables, and clean up after yourself.  Pack the artwork you bring carefully, and make sure to have extra packing supplies. Bring business cards, too--this way, even if someone isn’t able to buy a painting today, they can refer back to you later..  Pay for your booth or table at the convention on time; otherwise, your spot may go to someone else. Your paintings are what will hold most people’s attention, but you’ll need to catch their interest first. Decorate your booth in a way that matches your aesthetic and corresponds to your paintings to draw the eyes of potential customers.  Consider setting out small objects that correspond to your subjects (for instance, shells, if you like painting seascapes.) Bring a nice solid-colored tablecloth to make an even, professional-looking workspace.  A standing banner with your name, an art sample, and contact information on it can go almost anywhere, and commands attention without being too obnoxious. Now that you’re all set up, be friendly with the people who come by your table. Smile and say hi to browsers, and try to master the art of engaging in conversation without being too pushy. You can even consider doing quick commissions, like sketches or watercolors, for interested buyers.  If you don't know what to say when someone is looking at your work, a smile and a simple "Hi there!" or "Hello!" works wonders. It's easy to engage with buyers with sincere compliments ("I love your shoes!"), as well.
Start local. Apply early and with care. Be professional. Bring decorations to go with your paintings. Be engaging.