Join us for our Rockin' the Rock Garden live music concert series!

Join us for all the chocolate you can eat on the Chocolate Express. Be sure to hold on to your purse because the Iron Mountain James Gang will probably be lurking around.

Local Produce
Local Meats
Local Chefs
Local Beer & Wine

Join us for Rockin' the Rock Garden, our live music concert series!

The reunion is open to JHS gradutes! We will have a tailgate before the football game at the Pit and street party uptown hosted by the class of 1989 after the game. On Saturday the reunion will take place at the St Louis Iron Mountain Railway starting at 5. Food, drinks will be available. Free caboose rides. Project 573 band and an 80’s DJ. Join us! Tickets are available on EventBrite. https://www.eventbrite.com/e/jackson-high-school-multi-year-class-reunion-1984-1994-jackson-missouri-tickets-911510300847?utm-campaign=social&utm-content=attendeeshare&utm-medium=discovery&utm-term=listing&utm-source=cp&aff=ebdsshcopyurl

Join us for our live music concert series, Rockin' the Rock Garden!

Historic Uptown Jackson is the place to be for Oktoberfest- live music, local vendors, craft beer, pet parade, and so much more!

Starting after Thanksgiving through Christmas, join us the best Christmas train around. It's a themed train stuffed with Christmas Magic, songs, games, food, and fun! Reservations by phone only!

Springfest is Uptown Jackson's biggest fundraiser and highlight of the year! This annual event features a Piccadilly-style auction, a live auction, and a variety of fun games. Dinner is provided, and there is a cash bar available for your enjoyment. It’s a fantastic way to support a good cause while having a great time!

Jackson in Bloom is a celebration of spring on High Street.

This event focuses on landscaping, gardening, earth-friendly products/services, pets, kids, and outdoor activities. Get your hanging baskets and plants at the Jackson High School Plant Sale and other landscaping vendors, learn something about gardening and nature.

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Other activities include kid's corner, food, crafts, vendors and a dog show!

Jackson Oktoberfest is back!

We are excited to host this event on October 3-4, 2025. We will now be in our eleventh year and continuing to grow - expecting to attract more than 20,000 locals and travelers!

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Oktoberfest is presented in the style of a German Festival. We feature live music, authentic food and beer, and family-friendly activities to give one the sense of adventure that a trip to Munich would provide!

More information on the specifics of the event is on our Facebook page at:

www.facebook.com/UptownJacksonOktoberfest