With the dazzling words and sounds from last weekend still echoing, it’s not too early to save the date for next year’s Word of South festival: April 23-25, 2027. Miss an artist or want to relive the moments? Check out the 2026 festival playlist at open.spotify.com.
It’s May Day and a full Flower Moon First Friday, with fresh art around town and music from Naugahyde Park and RiverSide playing in the Railroad Square Art District.
The Tallahassee Symphony Orchestra goes out with a flourish for its season finale on May 2.
Here’s a roundup of entertaining events around Tallahassee, culled from emails, press releases, the Council on Culture & Arts, online listings and elsewhere.
1. TSO presents romantic closing concert of 45th season
Grammy-award winning pianist Michelle Cann will perform Liszt’s 1st Piano Concerto with the Tallahassee Symphony Orchestra at 7:30 p.m. May 2, 2026
Just as the Tallahassee Symphony Orchestra is closing out its season this weekend with Radiant Romance, tickets are going on sale for the 2026-27 Season of Dreams.
If you are a newcomer to TSO, check the open rehearsals at 10 a.m. May 2 in Ruby Diamond Concert Hall to observe the process that brings concerts to life. Then be transformed by music at 7:30 p.m. Tickets are $37-74. $25 tickets are available for students and children under 18. Call 850-224-0461 or visit 507 N Calhoun St. Visit tallahasseesymphony.org.
Tallahassee Symphony Orchestra Music Director Yaniv Dinur at the 2025 season opener. The 2026–2027 season is designed to deliver breathtaking performances and audience connection.
The program begins with the Prelude from Tristan und Isolde, where the longing of every unresolved phrase pulls you deeper into the passions and frustrations of these doomed lovers. Grammy winning pianist Michelle Cann performs Liszt’s Piano Concerto.
After intermission, the atmosphere shifts inward with Strauss’ profound Death and Transfiguration, a work that explores what lies beyond earthly existence. To close the milestone 45th Anniversary Season, Maestro Dinur leads Le Poème de l’extase, a radiant finale.
2. Ethel Cain back for two shows at The Moon
Ethel Cain will be in town for two Tallahassee shows at The Moon at 8 p.m. May 5 and May 6, 2026.
Fresh from a show at Coachella, Ethel Cain fans have two shots to see The Willoughby Tucker Forever Tour next week.
The Tallahassee native and “dream-pop” artist is returning to her stomping grounds for two shows at The Moon, 1105 E. Lafayette St., May 5-6. Doors open at 7 p.m., showtime is 8 p.m. General admission tickets are $83. Ages 17 or under must be accompanied by a parent or guardian. Ages 4 and under not admitted. Visit moonevents.com.
Ethel Cain will bring her Willoughby Tucker Forever Tour to Tallahassee for two shows at The Moon on May 5-6, 2026.
Known for Southern Gothic Americana music filled with personal twists, the singer-songwriter and record producer has partnered with The Ally Coalition to donate $1 from every ticket to organizations committed to serving the Trans community.
Ethel Cain is the stage name for 27-year-old Hayden Silas Anhedönia, who was born in Tallahassee and raised in Perry, Florida. Cain released “Willoughby Tucker, I Will Always Love You” in August, 2025.
3. Walking with Shakespeare at Tallahassee Museum
King Oberson and Queen Titania will be in the Southern Shakespeare Company’s “A Walking Midsummer Night’s Dream,” an outdoor theatrical adventure set at the Tallahassee Museum at 7:30 p.m. April 30-May 2 and May 7-9, 2026.
The Southern Shakespeare Company takes audiences on “A Walking Midsummer Night’s Dream,” a fully immersive, outdoor theatrical adventure set within the natural beauty of the Tallahassee Museum, 3945 Museum Drive, at 7:30 p.m. April 30-May 2 and May 7-9. Tickets are sold out, but there’s a waiting list and volunteer slots at facebook.com.
Over two magical weekends, small audience groups will be guided along woodland trails, encountering scenes from “A Midsummer Night’s Dream” unfolding in real time — complete with mischievous fairies on zip lines. They will be costumed as Florida bugs and insects to match with the natural Florida environment in a show with enchanted lovers, and high-flying surprises.
4. May Day songs at Blue Tavern
Paddy League will lead a night of May Days songs at 8 p.m. Friday, May 1, 2026.
Get your weekend started at Blue Tavern, 1206 N. Monroe St., with Two Clever at 5 p.m. Friday, followed at 8 p.m. with May Day: Songs of the Labor Movement with Paddy League and friends. Join Gina and Paddy, George Pettis, Isabel Ruano, Lili Forbes, members of Brazilian ensemble and Irish session players in some great songs about workers’ rights and the movements that work for justice. $10 cover.
Blue Tavern’s eclectic lineup on Saturday, May 2, begins with a Drag Brunch from noon-3 p.m. with Aida Lott presenting The Blue Tavern Cabaret Saturday Edition. Admission is $10. Tickets at instagram.com.
The Jug Band Jam hosted by the Green Street Sheiks begins at 4 p.m., followed at 8 p.m. by Grant Peeple’s 69th Birthday Party. Peeple’s is known for his axe-sharp socio-political tunes, raucous humor and heart-gigging ballads. He is the recipient of the Focus Foundation Award for Creative Excellence. Come help Grant celebrate 69 years on Earth. There will be birthday cake. $10 cover.
5. Take the ‘If This House Could Talk’ tour in Apalachicola
Photo from a past tour showing some of the storyboards in front of historic Apalachicola locations. This year’s self-guided tour runs May 2-17, 2026.
Head for the coast to catch salt air, great seafood and cool old houses this month. The Apalachicola Area Historical Society is hosting its popular self-guided historical tour, “If This House Could Talk,” May 2 through May 17 at over 30 locations in historic Apalachicola.
Storyboards, created by property owners and posted in front of a variety of fascinating homes, historic locations and buildings, share interesting and sometimes odd historical facts and stories of these Apalachicola places and their past residents. Guests are invited to view the storyboards (but not enter the properties) at their own pace during this free event.
Maps are available at the Raney House Museum, the Apalachicola Bay Chamber of Commerce, Oystertown Books, Eastpoint Visitors Center, Apalachicola Margaret Key Public Library, online at Apalachicolahistoricalsociety.org and at the AAHS Facebook page. More information can be found at apalachicolahistoricalsociety.org.
The AAHS Raney House Museum is located at 128 Market Street at the corner of Avenue F in Apalachicola and is open from 10 a.m.-4 p.m. Tuesday through Saturday.
OTHER EVENTS
Amicus Brewing: Kentucky Derby Watch Party with Chalk Line Trio, 4-10 p.m. Saturday, May 2, 717 S Gadsden St. Grab your hat and join Amicus Brewing Ventures and Harry’s Proper Burger for an evening of racing, live music, and southern-themed specials.
Big Bend Sierra Club: Monthly program meeting at 6:30 p.m. Thursday, April 30, at the Req Room, 1208 North Monroe St. Social hour will begin at 6:30 p.m. and the regular meeting will begin at 7 p.m. Bradley O’Hanlon will be giving a presentation on the reintroduction of the Indigo Snake into panhandle region of Florida.
Bird’s Aphrodisiac Oyster Shack: Old Porch Swing Quartet, 7-10 p.m. Friday, May 1, 325 North Bronough St.
Guitarist Shane Parish will play Blue Tavern on May 5, 2026.
Blue Tavern: Matthew Cravener plays happy hour at Blue Tavern, 1206 N. Monroe, at 5 p.m. Tuesday, May 5, followed at p.m. by Bluesday Tuesday: Blues Meets Girl. $5 cover. Happy hour Rad Reading at 5 p.m. Wednesday, May 6, followed at 8 p.m. by Open Mic Night. 1st Thursday Bluegrass Jam, 5 p.m. May 7. This month’s jam will be dedicated to the memory of the tavern’s dear departed friend and bluegrass mandolin monster, David Leporati. Guitarist Shane Parish is coming back to Tallahassee to deliver some phenomenal guitar work, original tunes and mind-blowing interpretations at 8 p.m. $10 cover.
First Friday at Railroad Square: RiverDogs, 7-9 p.m. Friday, May 1, The Other Side Vintage, 607 Railroad Square, Railroad Square Art District.
Getaway Grille and Bar: Charlie Morris Band, 7-10 p.m. Friday, May 1. Sawmill Jam, 7-10 p.m. Saturday, May 2, 2386 Allen Road.
Lake Tribe Brewing: Fiesta at Lake Tribe with Saylor Dollar Duo, 6-9 p.m. Friday, May 1, 3357 Garber Drive.
NorthFlora Collective: Naugahyde Park, 6-9 p.m. Friday, May 1, in Railroad Square. NorthFlora Collective is open at 11 a.m., live music and festivities start at 6 p.m. Special guest will be Ology Brewing handing out free beer and swag for First Friday.
Tallahassee Civic Chorale will present Together We Sing at Grace Lutheran Church at 7:30 p.m. Friday, May 1, 2026.
Tallahassee Civic Chorale: “Together We Sing,” 7:30 p.m. Friday, May 1, Grace Lutheran Church, 2919 Miccosukee Road. Celebrating its 40th anniversary, the concert features favorite songs from the Chorale’s first 40 years including pieces by Paul Basler (Five Songs of Faith), Marques Garret (Sing Out My Soul), Tucker Biddlecombe (The Greatest Ship), and Susan LeBarr (We Remember Them). Tickets are available online at CivicChorale.org and will be available at the door. Tickets are $15 for adults, $12 for seniors (62+) and students, and Free for TSC students, staff, and faculty. Seating in Grace Lutheran is non-reserved.
Tallahassee Downtown Market: Matthew Cravener Duo, 10 a.m.-noon, 115 E Park Ave.
Tallahassee Film Society: “Holding Liat,” 3 p.m. Saturday, May 2, and 5 p.m. Sunday, May 10, Challenger Center IMAX, 200 S. Duval St. “Natchez” holding over at 5 p.m. Sunday, May 3. General admission, $11; TFS members and students, $9.
“Purple Moon” by Leah MacDonald, part of “Layers,” at Venvi Gallery with reception from 5-8 p.m. May 1, 2026.
Venvi Art Gallery: Layers, by artist Leah Macdonald on display through May 17, with art reception from 5-8 p.m. Friday, May 1, at Venvi, 2901 E. Park Ave.
Village Square Annual Tallahassee Town Hall: In partnership with Leadership Tallahassee, Tallahassee Democrat, and WFSU, 6-8 p.m. Thursday, May 7, WFSU Studios, 1600 Red Barber Plaza. Register in advance. Visit tlh.villagesquare.us.
The Wine House: Longineu Parsons Ensemble, 7 p.m. Friday, May 1, 1355 Market St.
Have an event coming up? Email details to limelight@tallahassee.com.
This article originally appeared on Tallahassee Democrat: Top 5 fun things to do around Tallahassee this weekend