Booker Fest in Bay St. Louis Over Labor Day Weekend

What does it say about a town when its most explicitly local landmark draws visitors from beyond the area, while its oldest neighborhood tradition just got redesigned specifically to slow down for the people who already live here?

That question sits right inside this week's calendar. On Friday, September 4, 100 Men Hall opens its seventh annual Booker Fest, a three-day music weekend built to draw visitors from well outside Hancock County. Six days later, on September 12, Old Town's long-running Second Saturday tradition returns in a format the Old Town Merchants Association only started using this year. Same handful of blocks downtown. Two completely different reasons to be there.

A Festival That Draws Visitors from Beyond the Area

Booker Fest exists because of one person: James Carroll Booker III, a New Orleans-born pianist who spent part of his childhood in Bay St. Louis, raised by his aunt, Bessie Lizana, while he attended St. Rose de Lima and learned classical piano. He went on to influence Harry Connick Jr. and Dr. John, and he picked up nicknames along the way that tell you how much of a character he was: the Black Liberace, the Piano Pope, the Bayou Maharajah.

This year's festival runs Friday through Sunday, September 4 through 6, ahead of Labor Day itself on Monday the 7th. The lineup mixes touring acts with hall regulars: The Rumble, Water Seed, Lost Bayou Ramblers, the Joe Krown Trio plus one featuring Papa Mali, Maggie Koerner, Chris Vincent & The Raw Deals, and the St. Rose de Lima Gospel Choir, several of whose members actually sang alongside Booker when he played piano there. A few set times are locked in: Chris Vincent & The Raw Deals opens Friday at 6pm, the gospel choir takes the stage Saturday at 2pm, and Maggie Koerner follows at 3:30. The weekend wraps with Lost Bayou Ramblers, capped off with free jambalaya.

A weekend pass, called a Hall Pass, runs $110 for all three days. If you were counting on the early bird rate, that window already closed on August 10, so budget for full price. According to the hall's own numbers, Booker Fest typically draws more than 400 people from the region, from around the country, and from overseas. For one weekend a year, that audience converges on a three-block stretch of Old Town.

Why the Hall, Specifically

Here is the part that matters if you actually want to understand why this particular event draws visitors from beyond the area while so much else in town stays local. The Hall isn't a music venue that happens to be historic. It's a historic institution that happens to host music.

The association behind it was chartered in 1894 by the One Hundred Members' Debating Benevolent Association, and the physical building that still stands at 303 Union Street, tucked behind the Train Depot and three blocks from the beach, went up in 1922. For decades it functioned as one of the only places in town where the Black community could gather safely, and it later hosted touring blues, R&B, and jazz acts as part of the Chitlin Circuit. It sat closed for five years before Rachel Dangermond bought it in 2018 and resurrected the original 1894 charter as a nonprofit, and it now carries a marker on the Mississippi Blues Trail, one of the few standing buildings on that trail anywhere.

None of that is incidental to why Booker Fest draws a crowd from outside the county. People aren't traveling to Bay St. Louis for a generic music festival. They're traveling for a specific building with a specific history, which is a different kind of draw than a beach weekend or a seafood festival. It's the opposite of manufactured, and that is exactly what makes it work as an export.

Second Saturday Doesn't Work the Way It Used To

Now flip to the other end of the calendar. Second Saturday has been Old Town's monthly ritual for close to three decades, and until this year it ran on a fixed schedule: a single art walk block, roughly 4 to 7pm, with galleries and shops opening their doors at the same time.

That changed in 2026. The Old Town Merchants Association restructured the event so that "each highlighted business will create their own Second Saturday schedule," spreading specials, live music, and events across the day instead of concentrating everything into one three-hour window. It's a small operational shift, but it changes who the event is actually for. A single fixed block rewards someone planning a special trip around it. A day full of staggered, business-specific programming rewards someone who already lives close enough to wander in and out on their own timeline.

You can see how it plays out from the format's first test run back in January, when OTMA anchored the day around the Mockingbird Café's Dolly Parton-themed celebration on South Second Street, then let the day radiate outward toward Connie Bourgeois's Salon on Second Street and Magnolia Antiques at the corner of Second and Main. Mockingbird Café leaned into that same spotlight logic again this August, marking its 20th anniversary with a Woodstock-inspired party on August 8. That's a business using its own day inside the new format rather than waiting for a citywide 4-to-7 block to carry it.

OTMA has also been building out a separate, standalone events calendar alongside the monthly ritual. Battle in the Bay: The Art of the Cocktail debuted this past March 13 at 200 North Beach as the official kickoff to Souper Mudfest weekend, a ticketed cocktail competition among local bartenders that has nothing to do with the traditional art walk format at all. Between the reformatted Second Saturday and a new signature event like Battle in the Bay, OTMA is running two different kinds of programming at once: one built for daily foot traffic, one built as its own draw.

What This Actually Means for Your Week

So here is the practical shape of it. Booker Fest runs Friday through Sunday, September 4 to 6, ticketed, national in scope, staged at one address. Second Saturday returns the following weekend, September 12, free, spread across Old Town, paced by whichever businesses choose to lead that month. There is no overlap, no single weekend where you have to choose between the two, and no reason to try to cram both into one trip.

The Hall itself straddles both registers without missing a beat. The same building charging $110 for a national touring weekend also runs a free Writing Room every second Saturday from 10am to 1pm, led by novelist and arts activist Ellen Morris Prewitt, open to anyone who wants to sit down and write for a couple of hours. That session happens to land on September 12, the same day as the reformatted Second Saturday, which means the Hall is doing the ticketed festival version and the free community version in the same month, six days apart.

If you're stringing the two weekends into a full stretch of Old Town outings, there's a newer stop worth adding to the loop. Boonies on the Bayou, a stilt-built restaurant at 10408 MS-603 just two minutes off I-10, relocated here after a barbecue pop-up residency in Pearl River ended. It's run by chef Ricky Herring and Mikayla Capps, and the kitchen has already built a following around charbroiled oysters, a seafood bread stuffed with shrimp, crab, and crawfish, and a gumbo built on a beef tallow roux instead of the usual butter base. It's not downtown, and it's not part of either weekend's official programming, but it's the kind of newer, waterfront addition that fits naturally into a week already built around going out.

None of this is really about picking an event. It's about noticing that this town runs two different operating systems back to back, one designed to pull people in from outside, one redesigned this year to let the people already here move at their own pace, and that both versions of Bay St. Louis are worth showing up for.

If you're the kind of person who notices details like a reformatted Second Saturday or a hall that can host a national festival one week and a free writing circle the next, you probably already know this town rewards people who pay attention to it. That's true of the neighborhoods too, not just the calendar. If you're curious what that kind of attention looks like applied to a home search or a listing, Glenn-Marie Fitzgerald works this coast block by block. Get Your Home Value — Start Here.