The festival is a culmination of Maplewood and Richmond Heights’ most renowned restaurants, beloved boutiques, and unique specialty stores. In its 18th year the event’s vibe is distinct and unmistakable, radiating the culture and character of the businesses in the area. In addition to the food and libations, visitors will enjoy live entertainment on two stages. In 2026, things kick off on Friday evening, May 15th with a pre-party to the Taste of Maplewood Street Festival including live entertainment, food vendors, and more! The event continues the next day, on Saturday, May 16th with a full roster of vendors on the street offering their signature bites, libations, demonstrations, and unique items!