Coastal Mississippi’s Fall Calendar Turns Milestones Into Reasons to Visit
September 08, 2026
From live blues and songwriter sessions to classic cars, catamaran racing, art festivals and Gulf Coast seafood, Coastal Mississippi is heading into fall with a calendar that is as diverse as its 62 miles of shoreline. Beginning Labor Day weekend and continuing through November, the destination’s biggest events combine long-running local traditions with milestone celebrations that give travelers plenty of reasons to plan a coastal escape.
The season begins with the 7th Annual Booker Fest in Bay St. Louis and Artwalk Downtown Ocean Springs over Labor Day weekend, followed by the Biloxi Box Set Music Festival, Biloxi Seafood Festival and 35th Annual Gulf Coast Blues Festival. September also brings the Hobie 16 International Championship, drawing top catamaran sailors from around the world, and the Mississippi Songwriters Festival, where roughly 200 singer-songwriters will perform across Ocean Springs and Gautier. Later in the month, Banana Ball brings its deliberately unpredictable brand of baseball to Biloxi.
October shifts the spotlight to one of Coastal Mississippi’s biggest traditions, as Cruisin’ the Coast celebrates its 30th anniversary with more than 10,000 classic, antique and hot rod vehicles traveling along Highway 90. The fall calendar continues with the 40th Annual Fall Muster, the 10th Annual Gulf Coast Equality Fest and the century-plus Jackson County Blue Ribbon Fair. November brings the 48th annual Peter Anderson Arts & Crafts Festival in Ocean Springs, followed by Bud & Burgers in the Bay and the Scottish Highland Games and Celtic Music Festival.
The Curated Take: The appeal of Coastal Mississippi in fall isn’t simply that there is something happening every weekend. It’s that the events reveal the character of the destination. Music reflects its Southern and Gulf Coast roots, Cruisin’ the Coast turns the shoreline into a moving celebration, art festivals showcase local creativity, and sailing puts the region’s waterways center stage. For travelers, the calendar offers an easy reason to choose a particular weekend and then build a broader coastal getaway around it.
Photo credit: Coastal Mississippi / Visit Mississippi
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