I often tell my friends I am not a ride or die friend. I have questions. I need to know where we are going, how we are going to get there and why do we need to die. However, when Kerry Maloney called me and asked if I wanted to judge a Dolly Parton Highest Hair Contest I immediately said yes. As well as volunteering Kevinnie for a weekend in Bay St. Louis.
Each year the town of BSL celebrates Dolly Parton’s Birthday with the Dolly Should Festival. The reason for this name? Well Dolly Should attend, right? We were able to make a whole weekend out of this event, so we wanted to tell you a little bit about it.
Where We Stayed
We stayed at the most charming vintage motel right outside the heart of the town called The Driftwood Motel. The Driftwood was originally constructed in the early 1960’s to expand the offering of Mississippi hospitality and tourism along the Gulf Coast. New Orleans residents wanted a easy costal getaway and Bay St. Louis provided that. I late 2023 the motel was redeveloped and renovated to make it a shining star at the beginning of main street.
The original Driftwood Motel had a sign that said, “Free TV – TV – Telephone” which the new owners decided to keep and update to “Free TV – Pool – Wi-Fi”. This piece of nostalgia is both cute and comfortable offering several guest amenities like a kitchen where we found coffee, Diet Coke and King Cake!
What We Did
We started our trip checking into the Driftwood Motel. The location is right off of Main Street, so Kerry picked us up in her golf cart and we took a quick trip to our first destination.
100 Men Hall Gumbo Cook Off
“100 Men Hall is a thriving cultural center for music and community in the heart of Bay St. Louis. Built in 1922 by the One Hundred Members’ Debating Benevolent Association. Over the years the association sponsored many events and also rented the hall to promoters who brought in blues, rhythm & blues, and jazz acts. Local residents have recalled performances by Ray Charles, James Brown, Etta James, and numerous others here.” (please read more about their history here.)
“Owner Rachel Dangermond (and her son, Constantin “Tin” Dangermond, a/k/a the 101st Man) work to preserve culture, interprets history and gathers the community through live music events, innovative programs, and artistic expression.”
We were able to judge the Rock ‘N’ Roux Gumbo Cookoff where we sampled 16 different types of gumbo! Kevinnie and I as well as Scot Pilie and Ben Mount were the judges, and it was a lot harder of a job than I thought. We had to judge each gumbo on aroma, consistency, taste and presentation. Also trying 16 gumbo cups, even taking one bite, I was so full!! In the end we picked a winner and celebrated with the band!
Shops OF Century Hall Highest Hair Contest
Our next stop was the Shops of Century Hall. This historic building located on 2nd Stret and houses more than 25 local artisans and small shop owners. From original artwork to vintage clothing the Shops of Century Hall have it all. We took a shopping trip to pick up a vintage brooch and some fantastic catnip for Poydras and Peter.
This was the first year for their Highest Hair Contest and the women of BSL did not disappoint. The hair was amazing, and the women were entertaining and choosing a winner was almost impossible,
Mockingbird Cafe Dolly Look Alike Contest
Our last stop for the day (and third outfit change) was the Dolly Look Alike Contest at the Mockingbird Cafe! All the fun of the day culminated in this contest!!
What We Ate
Liked it so much we had it twice… Mockingbird Cafe was such a treat we ended up eating there for dinner Saturday night and Brunch Sunday morning.
For dinner we tried the Mockingbird Burger and the Dolly’s Taters.
For Brunch we had the 2nd Street Sandwich, Pulled Pork and Grits, as well as the hashbrown bowl. The 2nd Street Sandwich was phenomenal being both party sweet and savory. We ordered in on a croissant, but the highlight was truly the maple butter that was the sweet surprise in the center.
Other restaurants we want to try next time:
Creole Creamery
Thorny Oyster
The LOFT
Toro Sushi
Barracuda Taco Stand
Outfits
It’s not a Tiffany King post if we don’t include something about clothes.
The theme was obviously pink!
Outfit one: Hat and Cape were Blingdana, Top and Skirt are Old Navy, Boots are The Purple Tiger.
Outfit Two: I rented this from NUULY.
Outfit Three: Dress is Target, jacket is from Torrid last season (linked something similar).
Resources: Places to See and Shop
100 Men Hall
Mockingbird Cafe
Fleurty Girl BSL
Shops of Century Hall
Bay St. Louis Old Town
The Arts Hancock County
Downtown Dasher
What more Mississippi Content? Check out my other travel guides Ocean Springs, MS and Margaritaville.
XO,
Tiffany
Special thanks to Sklyar Theriot for tagging along with us for the weekend and capturing all of our content. Skylar is part of our Team at The Organized Social as well as a beautiful portrait photographer.
Leave a Reply