September is here, and there is plenty happening around St. Petersburg, Florida this month.
The Rays are home for several big series, the Rowdies have two special nights at Al Lang Stadium, downtown’s art scene comes alive for Second Saturday ArtWalk, The Florida Orchestra is putting a new spin on Taylor Swift and Pirates of the Caribbean, and there are plenty of free markets and waterfront events mixed in between.
Whether you are looking for sports, live music, art, family-friendly activities, or simply an excuse to spend an evening downtown, here are some of the best things happening around St. Pete in September 2026.
1. Catch the Rays at Tropicana Field
Throughout September
September starts with baseball right in the heart of St. Pete.
The Tampa Bay Rays host the New York Mets on September 1 and 2 at Tropicana Field before returning later in the month for home series against the Houston Astros, Athletics, and Boston Red Sox.
One of the biggest weekends comes September 18–20, when the Boston Red Sox visit Tropicana Field for a three-game series.
September's home schedule includes:
September 1–2: New York Mets
September 11–13: Houston Astros
September 15–17: Athletics
September 18–20: Boston Red Sox
With the regular season entering its final stretch, September is a great time to catch a game at the Trop.
2. Spend September 2 at the St. Pete Pier—or Shop the Night Market
September 2, 2026
If you are looking for something free to do, September 2 gives you a couple of options.
The St. Pete Pier hosts its free Sunset Yoga on the first Wednesday of the month, offering an outdoor workout with one of the city's best waterfront backdrops.
Or head over to Central Avenue for the St. Pete Night Market at Ferg's from 6–10 p.m.
The free monthly market features local small businesses and artists along with food, drinks, and vendors.
You could even make a full evening out of it—spend some time by the waterfront before heading toward Central Avenue.
3. Tampa Bay Rowdies Community Heroes Night
September 5, 2026 | 7:30 p.m.
Soccer fans get their first big St. Pete match of the month when the Tampa Bay Rowdies host Brooklyn FC at Al Lang Stadium on September 5.
The match is also Community Heroes Night, celebrating healthcare workers, first responders, and educators. The Rowdies are offering discounted ticket opportunities for qualifying community heroes.
Even if you are not a huge soccer fan, an evening match at Al Lang is one of the more uniquely St. Pete sports experiences—with downtown and the waterfront right outside the stadium.
4. Explore St. Pete's Art Scene During Second Saturday ArtWalk
September 12, 2026 | 5–9 p.m.
St. Petersburg's arts community takes over the city again on September 12 for the Second Saturday ArtWalk.
Galleries and studios across the Central Arts District, Grand Central District, Warehouse Arts District, Uptown Arts District, and downtown Waterfront District open their doors from 5–9 p.m.
Some participating studios are normally not open to the public, making ArtWalk a good opportunity to discover artists and spaces you may otherwise never see.
Best of all, you can turn it into an entire night out—explore the galleries and murals before stopping somewhere along Central Avenue for dinner or drinks.
5. Hear Taylor Swift's Music With a Full Orchestra
September 12, 2026 | 7:30 p.m.
September 12 is also a big night at the Mahaffey Theater.
The Florida Orchestra presents Steve Hackman's Taylor Swift: The Symphony Era, an original orchestral experience that reimagines music from throughout Taylor Swift's catalog.
The performance combines the orchestra with vocalists, a band, and the Master Chorale of Tampa Bay.
And for any Swifties wondering: Taylor Swift herself is not appearing at the performance.
Still, hearing familiar pop songs completely reconstructed for an orchestra could make this one of the more unusual concerts in St. Pete this month.
6. See Dalí in America Before It Leaves
Throughout September
September is also a good month to visit The Dalí Museum.
The museum's Dalí in America exhibition continues through October 18 and explores Salvador Dalí's relationship with the United States and the influence America had on his career.
The exhibition includes more than 70 paintings, drawings, photographs, and archival materials, covering everything from Dalí's first U.S. visit in 1934 to his work in fashion, film, advertising, and postwar American culture.
So if you have been saying you want to visit the Dalí “sometime,” September might be a good time to finally do it before the exhibition closes in October.
7. Watch Pirates of the Caribbean With a Live Orchestra
September 18 & 19, 2026
The Mahaffey has another fun event lined up later in the month.
The Florida Orchestra will perform the score to Disney's Pirates of the Caribbean: The Curse of the Black Pearl while the movie plays on screen.
There are two opportunities to catch it:
Friday, September 18 at 7:30 p.m.
Saturday, September 19 at 2 p.m.
If you have never watched a movie while its score is being performed live by a full orchestra, it is a completely different experience from watching it at home.
8. Rowdies Hispanic Heritage Night + Fireworks
September 19, 2026 | 7:30 p.m.
The Rowdies return home September 19 to face Birmingham Legion FC at Al Lang Stadium.
This match is Hispanic Heritage Night, celebrating the cultures represented throughout the team and the Tampa Bay community.
And after the match, fans can stick around for a postgame fireworks show over the bay.
Between the waterfront stadium, cultural celebration, and fireworks, this could be one of the best Rowdies nights of the season.
9. Shop Local at the St. Pete Sunday Market
September 20, 2026 | 11 a.m.–4 p.m.
For a more relaxed Sunday, the St. Pete Sunday Market returns September 20.
The free, family- and dog-friendly market can feature 100+ local artists, creators, and small businesses, along with food trucks, food vendors, fresh produce, drinks, and live music.
If you would rather shop local than spend another Sunday wandering through a big-box store, this is an easy way to support St. Pete businesses and make an afternoon out of it.
10. Little Big Town Comes to St. Pete
September 24, 2026 | 7:30 p.m.
Country fans have a major show to look forward to toward the end of the month.
Little Big Town brings its For The Art Of It Tour to the Mahaffey Theater on September 24.
The Grammy, ACM, CMA, and AMA-winning group has been performing together for more than two decades and is known for songs including “Pontoon,” “Girl Crush,” “Day Drinking,” and “Little White Church.”
It is one of several major September performances coming to the Mahaffey and a strong way to close out the month.
Bonus: Imagine Museum Has Events All Month
If none of those dates work, Imagine Museum has an especially busy September calendar.
Events scheduled throughout the month include:
Open mic poetry
Coffee tasting
Flamenco and Latin music
Dance socials
Mentalism and magic
Second Saturday programming
Stained-glass workshops
Sea-glass art
Live music
That makes it worth checking the museum calendar if you find yourself looking for something to do on a random weeknight.
September Is a Great Month to Explore St. Pete
One of the best parts about St. Petersburg is how much variety you can fit into a relatively small area.
In the same month, you can watch Major League Baseball at Tropicana Field, catch a Rowdies match beside the bay, explore local galleries during ArtWalk, hear a full orchestra perform a movie soundtrack, visit one of the city's museums, shop from local makers, or simply spend an evening walking the waterfront.
And you do not necessarily need to spend much to enjoy the city. Several September events—including the Night Market, Second Saturday ArtWalk, waterfront fitness events, and Sunday Market—are free to attend.
At Generations Tax & Wealth Management, Tampa Bay is more than where we work—it's our community. We enjoy sharing some of the events, businesses, and experiences that make the area such a great place to live.
Have a great September, St. Pete!
Event dates, times, schedules, and details were current as of August 26, 2026 and may be changed by organizers. Check directly with the event or venue before attending.