We have made it to the final stretch of summer. If you are like me, you want to squeeze every last drop of joy out of these long, golden days before the season turns. And the Gulf Coast delivers in a big way for Labor Day weekend. From the 70th annual Englewood Pioneer Days to the Venice Craft Festival and a Jimmy Buffett tribute concert with fireworks at Wellen Park, here is what is on my calendar for September 4-7.
Englewood Pioneer Days: 70th Annual Celebration
The 70th annual Englewood Pioneer Days runs September 5-7, and this year's theme is "70s Disco" which promises to be a whole lot of fun. This is one of the Gulf Coast's most beloved traditions, and it draws crowds from Sarasota all the way down to Charlotte County.
The weekend kicks off on Saturday, September 5, at 9 a.m. with the Cardboard Boat Races at Indian Mound. If you have never seen this event, imagine teams launching homemade cardboard boats into the water and racing them across the cove. Some sink immediately. Some glide across the finish line. Either way, it is hilarious and surprisingly competitive.
The main event is the Pioneer Days Parade on Monday, September 7 (Labor Day), at 9 a.m., running from Obee's parking lot down West Cowels Street to Dearborn Street and ending at the Veterans Memorial Pavilion. After the parade, the celebration continues at Pioneer Park (325 West Dearborn Street) with live entertainment, a pie-eating contest, a watermelon-eating contest, and vendor booths. It is classic small-town Americana on the Gulf Coast, and it is free to attend.
Englewood is about a 30-minute drive south from the Palmer Ranch corridor, and it makes for a lovely day trip. I like to combine the Pioneer Day festivities with a stop at the beach afterward — Manasota Key is just across the bridge.
No Filter Concert & Fireworks at Wellen Park: Friday, September 4
Downtown Wellen Park (north of Venice, just off US-41) is hosting a "No Filter" Concert on Friday, September 4, from 6 to 9:30 p.m. This is a Jimmy Buffett Tribute called "Fins Up Forever," and it comes with a fireworks show sponsored by HCA Florida. If you are a Parrothead, you will want to be there.
Wellen Park has become a lively community hub, with CoolToday Park (home of the Atlanta Braves spring training) at its center and a growing collection of shops and restaurants. The concert and fireworks are free, and the atmosphere is pure Gulf Coast — warm evening air, live music, and a sky full of color over a brand-new town center. Bring a blanket or chair and settle in for the evening.
17th Annual Venice Craft Festival: September 5-6
Downtown Venice (on Miami Avenue West) hosts the 17th Annual Labor Day Weekend Venice Craft Festival on Saturday and Sunday, September 5-6, from 10 a.m. to 4 p.m. This is a juried show featuring handmade crafts from artisans across the region — jewelry, pottery, woodworking, paintings, textiles, and more.
I love browsing the craft festival and then walking over to Venice Avenue for lunch at one of the sidewalk cafes. It is also the perfect opportunity to explore the historic downtown area, with its charming brick-lined streets, boutiques, and the lovely Venice Train Depot. Admission is free, and parking is available at the Venice Community Center with a shuttle.
Exotic Cars on the Circle: Saturday, September 5
Over on St. Armands Circle, the Sarasota Exotic Car Club presents Exotic Cars on the Circle on Saturday, September 5. This free event lines the Circle with rare and beautiful automobiles — Ferraris, Lamborghinis, Porsches, Aston Martins, and more. It draws car enthusiasts from all over the region, and the setting on St. Armands with its boutiques and restaurants makes it a full day out.
St. Armands Circle (adjacent to Bird Key) is one of the most iconic destinations in Sarasota, and the Exotic Cars event adds an extra sparkle to an already vibrant spot. Grab lunch or an early dinner at one of the Circle's excellent restaurants while you are there.
78th Annual Labor Day Regatta: September 5-6
For sailing enthusiasts, the Sarasota Sailing Squadron hosts the 78th Annual Labor Day Regatta on Saturday and Sunday, September 5-6. This is the longest-running annual regatta in the southeastern United States, dating back to 1946. Spectators can watch from the shoreline at the Sailing Squadron's facility on Sarasota Bay.
One Last Note on August: Events This Weekend
Before we jump into September, do not forget about the final events of August. The "Shared Light: Lynn Goldsmith" exhibition continues at Selby Gardens through September 13, making it a perfect Labor Day weekend activity as well. The Dueling Pianos night at the Art Ovation Hotel is this Friday, August 28, at 7 p.m., and the Murder Mystery Dinner is Saturday, August 29, at 6 p.m.
The Taste of Summer dining promotion wraps up on August 31, so this is your last chance to sample those prix-fixe menus at participating restaurants across Sarasota.
Whether you are heading to the Pioneer Days parade, strolling the craft festival in Venice, or watching the fireworks at Wellen Park, I hope you have a wonderful Labor Day weekend on the Gulf Coast. And if you have questions about any of the communities I cover on this site — from Palmer Ranch to Venice and Nokomis — I would love to help you explore your options.