What’s Happening in Pensacola This Weekend?!
What's Happening This Weekend in Pensacola, FL
October 9th – 11th, 2026
Fall is officially showing up around Pensacola, and this weekend is a really good one for getting out and enjoying the area. From Festa Italiana and thousands of handmade pumpkins to college basketball, live music on Pensacola Beach, a fishing clinic, and some Halloween-inspired fun, there’s plenty happening.
I’ve kept this list focused on Pensacola and Pensacola Beach, with a few nearby options that make sense for a local weekend guide.
FRIDAY, OCTOBER 9
Festa Italiana
Day: Friday, October 9
Time: 11:00 AM–6:00 PM
Place: Seville Square
Address: 311 E. Government Street, Pensacola, FL 32502
If you’re hungry, this is a great place to start the weekend. Festa Italiana celebrates Pensacola’s Italian heritage with Italian food, live music, demonstrations, a silent auction, prize drawings, dancing and activities for kids. Admission is free. Visit Pensacola
Helpful hint: Parking can fill up quickly around Seville Square. Consider parking a few blocks away and walking through the historic district.
20th Annual Glass & Ceramic Pumpkin Patch — First Pick Preview Party
Day: Friday, October 9
Time: 5:00–8:00 PM
Place: First City Art Center
Address: 1060 N. Guillemard Street, Pensacola, FL 32501
This is one of those very Pensacola fall traditions. First City Art Center brings together thousands of handmade glass and ceramic pumpkins created by local artists.
Friday night is the ticketed First Pick Preview Party, where guests get first access to the pumpkins before Saturday's public sale. There will also be music, art demonstrations, refreshments and drinks for guests 21+. PensacolaBeach.com
Helpful hint: If you want one of the really unique pumpkins, Friday is the night to go. The good ones go FAST.
Pensacola Beach Songwriters Festival
Day: Friday, October 9
Time: Various times throughout the evening
Place: Multiple Pensacola Beach locations
The Pensacola Beach Songwriters Festival continues throughout the weekend, with original songwriters performing at restaurants, resorts and beach venues. Many performances are free, although some special listening-room events require tickets. Pensacola Beach Songwriters Festival
A few Friday options include:
5:00 PM – Holiday Inn Beach Resort: Joel Shewmake, Josh Miller & Brent Loper
5:00 PM – Hilton Pensacola Beach: Chris Wallin, Anthony Smith & Mitch Rossell — ticketed listening room
7:00 PM – Paradise Bar & Grill: Pearl Clarkin, Cecilia Castleman & Karli Ryan
8:00 PM – The Pensacola Beach Resort/Salty Rose: Jason Grove, Jerry Vandiver & Brent Loper
8:00 PM – Bamboo Willies: Pauline Reese, Star DeAzlan & Julianna Rankin
10:00 PM – Flounders: Grace Michelle, Brennan Lowery & Karli Ryan Pensacola Beach Songwriters Festival
Helpful hint: Don't try to see everything. Pick one area of the beach and make an evening of it. Parking and walking between venues can take longer than you expect.
Costa at Laguna's Beach Bar & Grill
Day: Friday, October 9
Time: 8:00 PM–12:30 AM
Place: Laguna's Beach Bar + Grill
Address: 460 Pensacola Beach Boulevard, Pensacola Beach, FL 32561
Costa makes his Pensacola debut at Laguna's. This is an 18+ event, making it more of a late-night option for adults. PensacolaBeach.com
Helpful hint: If you're planning on spending the evening at Pensacola Beach, arrive early for dinner and parking rather than trying to show up right at 8 PM.
SATURDAY, OCTOBER 10
Pensacola Beach Songwriters Festival
Day: Saturday, October 10
Time: Various times
Place: Multiple Pensacola Beach venues
Saturday is packed with songwriter performances.
Some options include:
3:00 PM – The Pensacola Beach Resort/Salty Rose: Caitlin Mae, Kiersi Joli & Ivey Campbell
3:00 PM – Holiday Inn Beach Resort: Star DeAzlan, Pauline Reese & Julianna Rankin
5:00 PM – The Pensacola Beach Resort/Salty Rose: Jim McCormick, Michael Magno & Tris Weeks
6:00 PM – The Sandbar: Pauline Reese, Star DeAzlan & Kristen Foreman
8:00 PM – Bamboo Willies: Pearl Clarkin, Cecilia Castleman & Caitlin Mae
9:00 PM – Flounders: Joe Denim, Ray Scott & Brent Loper
10:00 PM – Flounders: Grace Michelle, Brennan Lowery & Karli Ryan Pensacola Beach Songwriters Festival
Helpful hint: This is a perfect weekend to grab dinner on Pensacola Beach and then walk to a songwriter performance afterward.
20th Annual Glass & Ceramic Pumpkin Patch
Day: Saturday, October 10
Time: 10:00 AM–2:00 PM
Place: First City Art Center
Address: 1060 N. Guillemard Street, Pensacola, FL 32501
Saturday is the free public pumpkin sale, with thousands of handmade glass and ceramic pumpkins available for purchase. There will also be food trucks, children's activities and music. Visit Pensacola
Helpful hint: Bring your patience — and don't wait until 1:45 PM. This is one of those events where the best pieces disappear early.
Sea No Limits Fishing Clinic
Day: Saturday, October 10
Time: 8:00 AM–12:00 PM
Place: Vince J. Whibbs Sr. Community Maritime Park
Address: 301 W. Main Street, Pensacola, FL 32501
Sea No Limits is a free fishing clinic for children and adults with intellectual and developmental disabilities and their families. It includes fishing instruction, casting and knot-tying activities, marine-life education and fishing along the waterfront. The first 250 registered participants receive a rod and reel, shirt and bait, and lunch is provided. Visit Pensacola
Helpful hint: Registration is important if you want to participate in the fishing activities and receive the included gear.
Landrum 5K Benefiting Lakeview Center
Day: Saturday, October 10
Time: 8:00–9:30 AM
Place: Landrum
Address: 219 E. Garden Street, Pensacola, FL 32502
This family-friendly 5K supports Lakeview Center and mental-health services throughout Northwest Florida. There will also be live music, food, games, children's activities, face painting and character meet-and-greets. Visit Pensacola
Helpful hint: You don't have to be a serious runner. It's a run/walk and is designed for families and participants of different ages.
Festa Italiana
Day: Saturday, October 10
Time: 11:00 AM–6:00 PM
Place: Seville Square
Address: 311 E. Government Street, Pensacola, FL 32502
Saturday is the main day to experience Festa Italiana, with Italian food, music, dancing, cultural demonstrations, children's activities and vendors. Admission is free. Visit Pensacola
Helpful hint: Go hungry. The food lineup alone is worth making a stop — shrimp scampi, lasagna, spaghetti and meatballs, sausage and peppers, cannoli, tiramisu and more.
WildFest
Day: Saturday, October 10
Time: 12:00–3:30 PM
Place: Wildlife Sanctuary of Northwest Florida
Address: 105 N. S Street, Pensacola, FL 32505
WildFest celebrates the Wildlife Sanctuary's 44th anniversary and includes wildlife encounters, birds on the glove, food, local art, conservation organizations and Halloween costumes. It's also a supply-drive event, so attendees are encouraged to bring something to help stock the sanctuary's shelves. Visit Pensacola
Helpful hint: This is a particularly good choice for families with kids who love animals.
Florida State vs. Auburn — Fall College Baseball
Day: Saturday, October 10
Time: 1:00 PM
Place: Blue Wahoos Stadium
Address: 351 W. Cedar Street, Pensacola, FL 32502
College baseball is coming back to Pensacola for a fall matchup between Florida State and Auburn. The Blue Wahoos are hosting several major college programs this fall. Visit Pensacola
Helpful hint: If you're looking for something casual and family-friendly, this is a great afternoon option before heading downtown or to the beach.
The Melody Community Fiesta
Day: Saturday, October 10
Time: 2:00–10:00 PM
Place: Seville Quarter Courtyard
Address: 130 E. Government Street, Pensacola, FL 32502
This free community celebration combines Latin American and Caribbean food, music, arts, culture and family activities. The evening transitions into an outdoor fiesta with DJs, dancing and live entertainment. Visit Pensacola
Helpful hint: This is a good one to pair with Festa Italiana since both are downtown — just be prepared for a busy afternoon/evening in the area.
Southern Tip-Off: Florida State vs. Mississippi State
Day: Saturday, October 10
Time: 5:00 PM; doors open at 4:00 PM
Place: Pensacola Bay Center
Address: 201 E. Gregory Street, Pensacola, FL 32502
College basketball officially arrives in Pensacola with Florida State taking on Mississippi State in the inaugural Southern Tip-Off. Tickets start at $10, making this a pretty affordable sports-night option. Pensacola Bay Center
Helpful hint: If you're going, buy tickets ahead of time and allow extra time for downtown parking.
Portside Pickle: Dinks for Dolly
Day: Saturday, October 10
Time: 8:00 AM–9:00 PM
Place: Portside Pickle
Address: 740 Commendencia Street, Pensacola, FL 32502
Calling all Dolly fans and pickleball players. This women's doubles tournament has a Dolly Parton theme, costume contest, vendors, food truck and DJs. Twenty percent of proceeds benefit Dolly Parton's Imagination Library, and participants can bring children's books for Gulf Coast Kid's House. Visit Pensacola
Helpful hint: This one is geared toward registered tournament participants, but the surrounding activities make it more than just a pickleball tournament.
SUNDAY, OCTOBER 11
Pensacola Beach Songwriters Festival — Beach Finale
Day: Sunday, October 11
Time: Various times
Place: Pensacola Beach
The Songwriters Festival wraps up its 2026 run on Sunday, with performances continuing around Pensacola Beach. One confirmed afternoon option is:
3:00 PM – Bamboo Willies: Anthony Smith, Brian Davis & Josiah Siska — ticketed Beach Finale. Pensacola Beach Songwriters Festival
Helpful hint: Sunday is a great day to enjoy the beach during the afternoon and finish the weekend with live music.
CCB Crafts & Drafts: Halloween Edition
Day: Sunday, October 11
Time: 2:00–4:00 PM
Place: Coastal County Brewing Company
Address: 3041 E. Olive Road, Pensacola, FL 32514
Get into the Halloween spirit with an afternoon of painting and beer. Participants create a lighted ceramic Halloween figurine, with five designs to choose from. The $30 price includes supplies and a complimentary 16-ounce beer. Visit Pensacola
Helpful hint: Supplies are limited, so this is one you'll want to reserve ahead of time rather than just showing up.
My Picks for the Weekend
If I were planning the perfect Pensacola weekend, I'd do:
Friday:
Festa Italiana → First City Art Center Pumpkin Preview → Pensacola Beach Songwriters Festival
Saturday:
Pumpkin Patch → lunch at Festa Italiana → Florida State vs. Auburn baseball → Southern Tip-Off basketball
Sunday:
Beach morning → Pensacola Beach Songwriters Festival → CCB Crafts & Drafts
And honestly, the Glass & Ceramic Pumpkin Patch is probably my can't-miss pick. It's uniquely Pensacola, supports local artists and makes for a really cool fall tradition.
A Little Local Tip
October is one of my favorite times of year around Pensacola because you can still enjoy the beach while the calendar starts filling up with fall festivals, outdoor events and Halloween activities. If you're heading downtown or to Pensacola Beach this weekend, give yourself extra time for parking, especially around Seville Square and the beach.
Event times and details can change, so it's always smart to confirm directly with the organizer before heading out. Pensacola Beach Songwriters Festival
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