• Christmas in July

    Downtown Prestonsburg Prestonsburg, KY, United States

    It may not yet be Christmas but that doesn't mean you can get in the spirit. Downtown will be merry, jolly, and bright with tons of great sales, products, free goodies, music, and more. Santa himself may even be making a special appearance to stock up on his Christmas gifts. Stores will stay open until […]

  • Star City Day

    Downtown Prestonsburg Prestonsburg, KY, United States

    Star City Day infuses small town, KY with art, music, and communal rejuvenation. The day of live art seeks to ignite the community’s senses with streets full of local artists, businesses, and food vendors! Welcomed to the whole family, enjoy your day in a vibrant and creative atmosphere while preparing for one of the largest […]

    Free
  • Cocktail Crawl

    Downtown Prestonsburg Prestonsburg, KY, United States

    Featuring: 4 Tasty craft cocktails from locally-loved hot spots Shuttle services provided to and from hotels & campground with local tour guides Unique Cocktail Tastings – Four “intoxicating” hours around 4 of the ‘Burg’s watering holes. Each stop will feature its own signature drink plus their own full menu of craft brews and tasty cocktails. […]

    $30
  • Jenny Wiley Festival

    Downtown Prestonsburg Prestonsburg, KY, United States

    The Jenny Wiley Festival consists of crafts, carnival, various vendors, car show, great local and national entertainment, parade, corn hole tournament, beauty pageant, and much more. Fun for all ages. IMPORTANT NOTE: Even with the mandated social distancing policy, we will be having a carnival this year, but things will be different. Social distancing and cleaning/sanitization […]

  • Small Business Saturday

    Downtown Prestonsburg Prestonsburg, KY, United States

    Small Business Saturday is an American shopping holiday held during the Saturday after US Thanksgiving during one of the busiest shopping periods of the year.