Summer is almost over, and there’s plenty to get excited about this weekend in Sarasota — from football season to Oktoberfest, with local bars hosting Bavarian-style beer bashes, including one of my favorites, Calusa Brewing.
There’s also a free outdoor movie screening to launch Hispanic Heritage Month, a tropical festival at Fishermen’s Village, a Talk Like a Pirate Day party (yes, really!), and a great spot to spend Friday or Saturday night with live music, good food and drinks in downtown Sarasota.
Looking for more ways to stay cool while still getting out of the house? Along with the five events highlighted below, The John and Mable Ringling Museum of Art is offering Sarasota-Manatee residents half-off admission every Saturday and Sunday this month. For details, visit ringling.org.
1. Oktoberfest ’25 at Calusa Brewing in Sarasota
The 190th Oktoberfest takes place in Munich from Saturday (Sept. 20) to Oct. 5, but of course, you don’t have to visit Germany to enjoy a quality Bavarian beer bash. Numerous Oktoberfest celebrations are happening across Sarasota-Manatee, including this party at Calusa Brewing.
That’s right — put on the lederhosen and dirndl and celebrate with the brewery’s showcasing of three German-inspired beers. The staff will be decked out in gear, too, and live German music from Petra & Teresa kicks off at 5:30 p.m. Food specials will be available from in-house restaurant Pigfish, which organizers say is serving dishes like bratwurst, pretzels, and “beer-braised everything.”
Noon Friday; Calusa Brewing, 5377 McIntosh Road, Sarasota; free admission; 941-552-8846; facebook.com/calusabrewing
2. Hispanic Heritage Month begins at The Bay Park in Downtown Sarasota
The Bay, a public park overlooking the water in downtown Sarasota adjacent to the Van Wezel, has unveiled a lineup of free programs celebrating Hispanic Heritage Month, which takes place Sept. 15-Oct. 15. The fun kicks off this evening (Sept. 18) with a screening of the original 1961 film version of “West Side Story.”
An adaptation of the 1957 hit Broadway musical of the same title — based on Shakespeare’s “Romeo and Juliet” —the movie stars Natalie Wood, Richard Beymer, Russ Tamblyn, Rita Moreno, and George Chakiris. It won 10 Academy Awards, including Best Picture. Bring your blankets and chairs, and remember: The Nest Café will be serving food and drinks, including beer and wine.
7:30 p.m. Thursday, Sept. 18; The Bay, 1055 Boulevard of the Arts, Sarasota; free; thebaysarasota.org
3. Key Lime and Tropical Fest at Fishermen’s Village in Punta Gorda
Fishermen’s Village, hugging Charlotte Harbor near downtown Punta Gorda, is always a fun destination with its shops and restaurants on the first floor and resort suites on the second. On Saturday, it will host one of its signature events: the Key Lime and Tropical Fest.
The annual event features live music by The Kollections, Pirates of the Floridian, and Tropical Avenue; restaurants serving tropical food and drinks; and vendors showcasing their creations.
Noon-9 p.m. Saturday; Fishermen’s Village, 1200 W. Retta Esplanade, Punta Gorda; free admission/parking; 941-639-8721; fishermensvillage.com
4. Talk Like a Pirate Day at Loaded Cannon Distillery in Bradenton
The Anna Maria Island Privateers invade Loaded Cannon Distillery to celebrate International Talk Like a Pirate Day — which is actually a thing, created in 1995 — with Bloody Mary specials, live music, raffle items, photo ops with the pirates and their ship, and swag bags for everyone who dresses up.
6-9 p.m. Friday; Loaded Cannon Distillery, 3115 Lakewood Ranch Blvd. Suite 110, Bradenton; 941-900-1482; loadedcannondistillery.com
5. Brian Byrd Band at Cask & Ale in downtown Sarasota
Craft cocktails and creative cuisine have made Cask & Ale on Main Street in downtown Sarasota a popular destination. I know this because nearly every time I stroll by during their weekday happy hour — featuring deals on drinks and bites such as their excellent burger from 4 to 7 p.m. — I struggle to snag a couple of seats at the bar. On Friday and Saturday nights, the place is even more packed.
Credit lap steel virtuoso, gifted singer, and bandleader Brian Byrd, who leads the live music from 7 to 11 p.m., filling the bar and dining area — with the party often spilling onto the sidewalk seating, where a separate bar is set up just to accommodate those enjoying the eclectic sounds inside and out. Byrd can play anything from gospel and country to R&B and pop, with his band frequently welcoming special guests who help shape the night’s direction. 7-11 p.m. Friday and Saturday; Cask & Ale, 1548 Main St., Sarasota; 941-702-8740; caskalesrq.com
Wade Tatangelo is Ticket Editor for the Sarasota Herald-Tribune and Florida Regional Dining and Entertainment Editor for the USA TODAY Network. Follow him on Facebook, Instagram, and X. He can be reached by email at wade.tatangelo@heraldtribune.com. Support local journalism by subscribing.
This article originally appeared on Sarasota Herald-Tribune: Looking for fun things to do this weekend? Top 5 Sarasota events Sept. 18-21
Reporting by Wade Tatangelo, Sarasota Herald-Tribune / Sarasota Herald-Tribune
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