The Pensacola area has 13 Christmas events for kids we could confirm for the 2026 season, from Downtown Pensacola Holiday Lighting Ceremony in Pensacola on November 4 to Winterfest: Photos with the Grinch in Pensacola, which runs through December 24. 8 of them are free, and every listing links straight to the host. It is one stop on our guide to Christmas events for kids in Florida, part of our guide for every state.
The short version
- 13 kids’ Christmas events confirmed in Pensacola for 2026, in Pensacola, Gulf Breeze, Milton, Navarre and Pace
- First: Downtown Pensacola Holiday Lighting Ceremony, Pensacola, November 4. Runs latest: Winterfest: Photos with the Grinch, Pensacola, through December 24
- Free: Downtown Pensacola Holiday Lighting Ceremony, Winterfest Christmas Special Stage Show, Elf Parade & Christmas Jubilee, Saturday with Santa (Milton), Gingerbread House Competition, Saturday with Santa (Gulf Breeze), Saturday with Santa (Navarre) and Saturday with Santa (Pace)
- Checked on each host’s own page; each listing links straight to it
Below is every event we could confirm, grouped by city, with the date, time, cost and the small things parents ask about (sign-ups, ages, what is included). Looking for a Santa train instead? Those are on our Florida Christmas train rides page.
Pensacola Christmas events for kids at a glance
- Kids’ Christmas events
- 13 confirmed for 2026
- Cities
- Pensacola, Gulf Breeze, Milton, Navarre and Pace
- Season
- November 4 to December 24, 2026
- Free events
- 8
- Kinds of events
- holiday show, story time with Santa, Santa visit and tree lighting
- Last checked
Plan your December
When each Pensacola Christmas event for kids happens
The first is Downtown Pensacola Holiday Lighting Ceremony in Pensacola on November 4; the last runs to December 24. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.
- Downtown Pensacola Holiday Lighting CeremonyPensacola · Nov 4
- Winterfest Christmas Special Stage ShowPensacola · Nov 20 to Dec 24
- Winterfest: Photos with SantaPensacola · Nov 20 to Dec 24
- Winterfest: Photos with the GrinchPensacola · Nov 20 to Dec 24
- Cirque Dreams HolidazePensacola · Nov 21
- Elf Parade & Christmas JubileePensacola · Nov 27
- Charles Dickens' A Christmas CarolPensacola · Nov 30
- Saturday with Santa (Milton)Milton · Dec 5
- Gingerbread House CompetitionPensacola · Dec 12
- Saturday with Santa (Gulf Breeze)Gulf Breeze · Dec 12
- Ballet Pensacola's The NutcrackerPensacola · Dec 18 to Dec 20
- Saturday with Santa (Navarre)Navarre · Dec 19
- Saturday with Santa (Pace)Pace · Dec 19
Look inside the book
Story time with Santa in Pensacola? Bring Rally home.
Rally Takes the Train is a five-minute rhyming picture book about a corgi’s first train ride, hand-painted in real watercolor. It makes a cozy bedtime story after a big day with Santa. Turn a few pages here.
Rally Takes the Train
Eight pages from the book
Turn the page
That's 8 of 25 pages
See who’s waiting at the station
Grandmommy and Papa are at the last stop. Get the full hand-painted book, $16.99 on Amazon.
See the full bookPage 1 of 8
Like it so far? See the full book
25 hand-painted pages, paperback, $16.99 with fast shipping from Amazon.
Every page is real watercolor on paper, painted by hand by Leslie Dunn. Nothing in this book was made with AI.
Christmas events for kids in Pensacola
9 confirmed events for kids in Pensacola, soonest first.
Pensacola: Downtown Pensacola Holiday Lighting Ceremony
Tree lightingFreeDowntown Improvement Board · Pensacola
- Host
- Downtown Improvement Board (opens in a new tab)
- Where
- Plaza Ferdinand VII, 309 S Palafox St, Pensacola, FL 32502
- When
- Wednesday, November 4, 2026, 3:30 to 8 pm
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
Downtown Pensacola launches a seven-week holiday season on Wednesday, November 4, 2026. Santa shows up at 3:30 p.m. by the Christmas tree at the Pensacola Museum of History if the weather allows, and families can snap selfies and tell him their wishes until 4:45 p.m.
At 5 p.m. the switch is flipped on more than half a million lights along Palafox Street and nearby, with Santa and the Winterfest Grinch standing in front of the museum. The Winterfest mini-train rolls around Plaza Ferdinand from 5 to 8 p.m. The first Palafox Market Holiday Edition is also open from 4 to 8 p.m. Downtown offers free parking as well as paid parking at $1 an hour.
Parent tip: Weather could affect things. Come early for Santa photos ahead of the 5 pm lighting.
See dates and details from Downtown Improvement Board (opens in a new tab)Pensacola: Winterfest Christmas Special Stage Show
Holiday showFreePensacola Winterfest · Pensacola
- Host
- Pensacola Winterfest (opens in a new tab)
- Where
- Winterfest Plaza, 223 S Palafox Pl, Pensacola, FL 32502
- When
- Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
The Winterfest Christmas Special is a 30 minute performance on the front steps at the Artel Gallery at Winterfest Plaza, 223 S. Palafox Place. Audiences meet the Polar Express conductor with his dancing crew, Charlie Brown and the Peanuts gang, Rudolph with his Reindeer Rockettes, and more figures from well known Christmas tales.
The dances are set to seasonal favorites including Rockin Around the Christmas Tree, White Christmas, Run Run Rudolph and Holly Jolly Christmas. A new show begins every half hour on Winterfest nights, and entry costs nothing. The ticketed trolley tours that Winterfest offers are separate, and this listing covers just the plaza show.
Parent tip: The show repeats every half hour, and dates match the Winterfest schedule.
See dates and details from Pensacola Winterfest (opens in a new tab)Pensacola: Winterfest: Photos with Santa
Santa visitPensacola Winterfest · Pensacola
- Host
- Pensacola Winterfest (opens in a new tab)
- Where
- Winterfest Plaza, 223 S Palafox Pl, Pensacola, FL 32502
- When
- Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026
- Cost
- Photo packages from about $39 to $55 plus add-ons
- Ages
- All ages
- Sign-up
- Recommended
- Confirmed
- On the host’s page, checked
Each night of Pensacola Winterfest, Santa Claus waits in his sleigh on the plaza at 223 South Palafox Place. The sleigh has been redesigned for whole families, and large groups can sit on presents outside it for the photo. Only one reservation is needed per photo group.
Packages include candids and one pose, with extra poses available for an added fee, and digital photos arrive instantly on your phone. Prices vary by night, with 2026 package listings starting around $39 and reaching about $55 on busy nights. Guests can reserve a time online or in person at Winterfest. Check the Winterfest site for each night's schedule.
Parent tip: Reserve a time online; prices are higher on peak nights.
See dates and details from Pensacola Winterfest (opens in a new tab)Pensacola: Winterfest: Photos with the Grinch
Holiday eventPensacola Winterfest · Pensacola
- Host
- Pensacola Winterfest (opens in a new tab)
- Where
- Winterfest Plaza, 223 S Palafox Pl, Pensacola, FL 32502
- When
- Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026
- Cost
- Photo packages from about $39 to $55 plus add-ons
- Ages
- All ages
- Sign-up
- Recommended
- Confirmed
- On the host’s page, checked
The Grinch, Santa's famous rival, lets guests drop by for a picture or two at Pensacola Winterfest. His spot is behind Santa's sleigh in downtown Pensacola, and visitors are escorted to his throne, where the whole family sits on seats made to look like trash cans for the photo.
As with the Santa pictures, you can book a slot either on the Winterfest website or on site, and the setup fits an entire family. Packages come with candid shots and one posed picture, additional poses cost extra, and every digital photo is sent straight to your phone. Check the Winterfest site for open nights and pricing.
Parent tip: Book online. The Grinch has his own line, apart from Santa's.
See dates and details from Pensacola Winterfest (opens in a new tab)Pensacola: Cirque Dreams Holidaze
Holiday showPensacola Saenger Theatre · Pensacola
- Host
- Pensacola Saenger Theatre (opens in a new tab)
- Where
- Saenger Theatre, 118 S Palafox St, Pensacola, FL 32502
- When
- Saturday, November 21, 2026, 7 pm
- Cost
- Ticketed, see host page
- Ages
- Entire family
- Sign-up
- Required ahead of time
- Confirmed
- On the host’s page, checked
Cirque Dreams Holidaze brings a holiday theatrical event wrapped around contemporary circus arts to the Saenger Theatre on Saturday, November 21, 2026, at 7:00 p.m. The Saenger calls it a holiday spectacular for the entire family and says the show has been reimagined for 2026.
The story follows young Clara on Christmas Eve, when a snowstorm threatens to keep her family away and two whimsical singers carry her into a fantastical world of color and wonder. The production runs about 90 minutes. All seats are ticketed, so buy in advance through the Saenger.
Parent tip: Evening show of about 90 minutes.
See dates and details from Pensacola Saenger Theatre (opens in a new tab)Pensacola: Elf Parade & Christmas Jubilee
Holiday paradeFreePensacola Winterfest · Pensacola
- Host
- Pensacola Winterfest (opens in a new tab)
- Where
- Winterfest Plaza, 223 S Palafox Pl, Pensacola, FL 32502
- When
- Friday, November 27, 2026, 2 pm
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
The Pensacola Elf Parade is the grand kickoff to the 2026 holiday season in downtown Pensacola, held on Friday, November 27, 2026. The parade is free for everyone and starts at 2:00 p.m., with a contest judging at 1:25 p.m. before it begins.
Families can color and wear elf ears, dress in an elf outfit, wear an ugly holiday sweater, or decorate a wagon or stroller. During lineup, anyone can join any contest, and Santa announces the winners just before the march. Each winner leads their section of the parade. Ticketed Winterfest trolley tours start later in the evening, but the parade itself needs no ticket.
Parent tip: Join the contests during parade lineup, before the 2 pm start.
See dates and details from Pensacola Winterfest (opens in a new tab)Pensacola: Charles Dickens' A Christmas Carol
Holiday showPensacola Saenger Theatre · Pensacola
- Host
- Pensacola Saenger Theatre (opens in a new tab)
- Where
- Saenger Theatre, 118 S Palafox St, Pensacola, FL 32502
- When
- Monday, November 30, 2026, 7:30 pm
- Cost
- Ticketed, see host page
- Ages
- Family audiences
- Sign-up
- Required ahead of time
- Confirmed
- On the host’s page, checked
A national tour of Charles Dickens' A Christmas Carol comes to the Saenger Theatre on Monday, November 30, 2026, at 7:30 p.m., and doors open at 6:30 p.m. The story follows Ebenezer Scrooge as the spirits of Jacob Marley and of Christmas Past, Present and Future lead him along.
The Saenger calls its version true to the story and full of fun, with projected images, period style sets and giant puppets, and says the tale shows every generation, from kids to grandparents, why kindness matters. A few scenes are spooky, so older kids will enjoy it more than toddlers. Every seat is reserved, and you need a ticket to attend.
Parent tip: A few ghost scenes are scary, so it works best for school-age kids.
See dates and details from Pensacola Saenger Theatre (opens in a new tab)Pensacola: Gingerbread House Competition
Santa visitFreeStuder Community Institute · Pensacola
- Host
- Studer Community Institute (opens in a new tab)
- Where
- Studer Community Institute, 220 W Garden St, Pensacola, FL 32502
- When
- Saturday, December 12, 2026, 11 am to 2 pm
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
The Studer Community Institute hosts its yearly Gingerbread House Competition for the public on Saturday, December 12, 2026, from 11:00 a.m. to 2:00 p.m. at 220 W. Garden Street. Guests can look at gingerbread builds in five divisions, root for their picks and watch prizes go to the best entries. The theme this year is Polar Express.
Other activities include a North Pole stop to have your picture taken with Santa, bingo, decorating cookies and seasonal snacks. Entry costs nothing. Families who want to submit their own gingerbread creation can sign up through the link posted on the institute's page.
Parent tip: Attending is free. Register only if you plan to enter a house of your own.
See dates and details from Studer Community Institute (opens in a new tab)Pensacola: Ballet Pensacola's The Nutcracker
Holiday showBallet Pensacola · Pensacola
- Host
- Ballet Pensacola (opens in a new tab)
- Where
- Saenger Theatre, 118 S Palafox St, Pensacola, FL 32502
- When
- Fri December 18 (7 pm), Sat December 19 (1:30 to 7 pm) and Sun December 20 (1:30 pm), 2026
- Cost
- Ticketed, see host page
- Ages
- Family friendly
- Sign-up
- Required ahead of time
- Confirmed
- On the host’s page, checked
Ballet Pensacola presents The Nutcracker at the Saenger Theatre as a holiday celebration for the whole family. Audiences follow Clara on an adventure that includes the battle with the Mouse King and a journey through snow and the Sugar Kingdom, set to Tchaikovsky's music with costumes and choreography.
Performances are Friday, December 18 at 7:00 p.m., Saturday, December 19 at 1:30 p.m. and 7:00 p.m., and Sunday, December 20 at 1:30 p.m., all in 2026. The two afternoon matinees may suit younger children best. Tickets are sold through the Saenger, and the ballet's page links to ticketing options.
Parent tip: Choose a matinee for younger children.
See dates and details from Ballet Pensacola (opens in a new tab)Christmas events for kids in Gulf Breeze
1 confirmed event for kids in Gulf Breeze, soonest first.
Gulf Breeze: Saturday with Santa (Gulf Breeze)
Story time with SantaFreeSanta Rosa County Library System · Gulf Breeze
- Host
- Santa Rosa County Library System (opens in a new tab)
- Where
- Gulf Breeze Library, 1060 Shoreline Dr, Gulf Breeze, FL 32561 (near Pensacola)
- When
- Saturday, December 12, 2026, 10 to 11:30 am
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
Santa Rosa County Libraries host Saturday with Santa, a series in which Santa takes a break from North Pole preparations to visit local libraries. Children are treated to a Christmas story and a gift from Santa, and families are asked to bring a camera if they would like a picture with him.
The visit at this branch runs from 10:00 to 11:30 a.m. on Saturday, December 12, 2026. All ages are welcome. The series is sponsored by area Friends of the Library, and the other branches visit on the other December Saturdays. For questions, call the library system at 850-981-7323.
Parent tip: Bring a camera for your own photo with Santa.
See dates and details from Santa Rosa County Library System (opens in a new tab)Christmas events for kids in Milton
1 confirmed event for kids in Milton, soonest first.
Milton: Saturday with Santa (Milton)
Story time with SantaFreeSanta Rosa County Library System · Milton
- Host
- Santa Rosa County Library System (opens in a new tab)
- Where
- Milton Library, 5541 Alabama St, Milton, FL 32570 (near Pensacola)
- When
- Saturday, December 5, 2026, 10 to 11:30 am
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
Santa Rosa County Libraries host Saturday with Santa, a series in which Santa takes a break from North Pole preparations to visit local libraries. Children are treated to a Christmas story and a gift from Santa, and families are asked to bring a camera if they would like a picture with him.
The visit at this branch runs from 10:00 to 11:30 a.m. on Saturday, December 5, 2026. All ages are welcome. The series is sponsored by area Friends of the Library, and the other branches visit on the other December Saturdays. For questions, call the library system at 850-981-7323.
Parent tip: Bring a camera for your own photo with Santa.
See dates and details from Santa Rosa County Library System (opens in a new tab)Christmas events for kids in Navarre
1 confirmed event for kids in Navarre, soonest first.
Christmas events for kids in Pace
1 confirmed event for kids in Pace, soonest first.
Pace: Saturday with Santa (Pace)
Story time with SantaFreeSanta Rosa County Library System · Pace
- Host
- Santa Rosa County Library System (opens in a new tab)
- Where
- Pace Library, 4499 Pace Patriot Blvd, Pace, FL 32571 (near Pensacola)
- When
- Saturday, December 19, 2026, 10 to 11:30 am
- Cost
- Free
- Ages
- All ages
- Confirmed
- On the host’s page, checked
Santa Rosa County Libraries host Saturday with Santa, a series in which Santa takes a break from North Pole preparations to visit local libraries. Children are treated to a Christmas story and a gift from Santa, and families are asked to bring a camera if they would like a picture with him.
The visit at this branch runs from 10:00 to 11:30 a.m. on Saturday, December 19, 2026. All ages are welcome. The series is sponsored by area Friends of the Library, and the other branches visit on the other December Saturdays. For questions, call the library system at 850-981-7323.
Parent tip: Bring a camera for your own photo with Santa.
See dates and details from Santa Rosa County Library System (opens in a new tab)Looking further afield? Our Florida Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Miami, Tampa, Orlando, Jacksonville, Fort Myers, Tallahassee, Gainesville, Sarasota, Fort Lauderdale, St. Petersburg and West Palm Beach. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first train ride, hand-painted in real watercolor by Leslie Dunn. $16.99 on Amazon, ages 0 to 8.
Buy on AmazonPensacola Christmas events for kids: questions parents ask
What Christmas events for kids are in Pensacola in 2026?
We confirmed 13 Christmas events for kids in Pensacola for 2026 on each host’s own page: Downtown Pensacola Holiday Lighting Ceremony in Pensacola (November 4), Winterfest Christmas Special Stage Show in Pensacola (November 20), Winterfest: Photos with Santa in Pensacola (November 20), Winterfest: Photos with the Grinch in Pensacola (November 20), Cirque Dreams Holidaze in Pensacola (November 21), Elf Parade & Christmas Jubilee in Pensacola (November 27), Charles Dickens' A Christmas Carol in Pensacola (November 30), Saturday with Santa (Milton) in Milton (December 5), Gingerbread House Competition in Pensacola (December 12), Saturday with Santa (Gulf Breeze) in Gulf Breeze (December 12), Ballet Pensacola's The Nutcracker in Pensacola (December 18), Saturday with Santa (Navarre) in Navarre (December 19) and Saturday with Santa (Pace) in Pace (December 19). Every one is listed below with times, cost and a link to the host.
What Christmas events for kids are in Pensacola, Florida?
For families in and around Pensacola, the confirmed Christmas events for kids this season are: Downtown Pensacola Holiday Lighting Ceremony (Wed, Nov 4, 3:30 to 8 pm, free); Winterfest Christmas Special Stage Show (Winterfest nights, Nov 20 to Dec 24, shows every 30 minutes, free); Winterfest: Photos with Santa (Select nights, Nov 20 to Dec 24, photo packages from about $39 to $55 plus add-ons); Winterfest: Photos with the Grinch (Select nights, Nov 20 to Dec 24, photo packages from about $39 to $55 plus add-ons); Cirque Dreams Holidaze (Sat, Nov 21, 7 pm, ticketed, see host page); Elf Parade & Christmas Jubilee (Fri, Nov 27, parade at 2 pm, free); Charles Dickens' A Christmas Carol (Mon, Nov 30, 7:30 pm, ticketed, see host page); Gingerbread House Competition (Sat, Dec 12, 11 am to 2 pm, free); Ballet Pensacola's The Nutcracker (Dec 18 to 20, evening shows and matinees, ticketed, see host page). Details and the host’s link for each are in the Pensacola section of this page.
What Christmas events for kids are in Gulf Breeze, Florida?
For families in and around Gulf Breeze, the confirmed Christmas events for kids this season are: Saturday with Santa (Gulf Breeze) (Sat, Dec 12, 10 to 11:30 am, free). Details and the host’s link for each are in the Gulf Breeze section of this page.
What Christmas events for kids are in Milton, Florida?
For families in and around Milton, the confirmed Christmas events for kids this season are: Saturday with Santa (Milton) (Sat, Dec 5, 10 to 11:30 am, free). Details and the host’s link for each are in the Milton section of this page.
What Christmas events for kids are in Navarre, Florida?
For families in and around Navarre, the confirmed Christmas events for kids this season are: Saturday with Santa (Navarre) (Sat, Dec 19, 10 to 11:30 am, free). Details and the host’s link for each are in the Navarre section of this page.
What Christmas events for kids are in Pace, Florida?
For families in and around Pace, the confirmed Christmas events for kids this season are: Saturday with Santa (Pace) (Sat, Dec 19, 10 to 11:30 am, free). Details and the host’s link for each are in the Pace section of this page.
Are there free Christmas events for kids in Pensacola?
Yes. 8 of the 13 events here are free: Downtown Pensacola Holiday Lighting Ceremony in Pensacola, Winterfest Christmas Special Stage Show in Pensacola, Elf Parade & Christmas Jubilee in Pensacola, Saturday with Santa (Milton) in Milton, Gingerbread House Competition in Pensacola, Saturday with Santa (Gulf Breeze) in Gulf Breeze, Saturday with Santa (Navarre) in Navarre and Saturday with Santa (Pace) in Pace. Some free events still ask you to register, so check each listing.
Where can kids see Santa in Pensacola this December?
Santa appears at Downtown Pensacola Holiday Lighting Ceremony in Pensacola (November 4), Winterfest: Photos with Santa in Pensacola (November 20), Elf Parade & Christmas Jubilee in Pensacola (November 27), Saturday with Santa (Milton) in Milton (December 5), Gingerbread House Competition in Pensacola (December 12), Saturday with Santa (Gulf Breeze) in Gulf Breeze (December 12), Saturday with Santa (Navarre) in Navarre (December 19) and Saturday with Santa (Pace) in Pace (December 19). Times and booking rules are in each event’s listing above.
Where are there Christmas story times for kids in Pensacola?
Holiday story times on this page: Saturday with Santa (Milton) in Milton, Saturday with Santa (Gulf Breeze) in Gulf Breeze, Saturday with Santa (Navarre) in Navarre and Saturday with Santa (Pace) in Pace. Library story times are usually free; story times with a meal or show are ticketed.
Are there kids' Christmas events in Pensacola on Christmas Eve or after Christmas?
Yes: Winterfest Christmas Special Stage Show in Pensacola (through December 24), Winterfest: Photos with Santa in Pensacola (through December 24) and Winterfest: Photos with the Grinch in Pensacola (through December 24).
How much is Downtown Pensacola Holiday Lighting Ceremony in Pensacola?
Free. Downtown Pensacola Holiday Lighting Ceremony is on Wednesday, November 4, 2026, 3:30 to 8 pm at Plaza Ferdinand VII. Confirm on the host’s page before you go.
How much is Winterfest Christmas Special Stage Show in Pensacola?
Free. Winterfest Christmas Special Stage Show is on Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026 at Winterfest Plaza. Confirm on the host’s page before you go.
How much is Winterfest: Photos with Santa in Pensacola?
Photo packages from about $39 to $55 plus add-ons. Winterfest: Photos with Santa is on Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026 at Winterfest Plaza. Confirm on the host’s page before you go.
How much is Winterfest: Photos with the Grinch in Pensacola?
Photo packages from about $39 to $55 plus add-ons. Winterfest: Photos with the Grinch is on Fri November 20, Sun November 22, Fri November 27, Sat November 28, Fri December 4, Sat December 5, Fri December 11, Sun December 13, Fri December 18, Sat December 19, Sun December 20, Mon December 21, Tue December 22, Wed December 23 and Thu December 24, 2026 at Winterfest Plaza. Confirm on the host’s page before you go.
How much is Cirque Dreams Holidaze in Pensacola?
Ticketed, see host page. Cirque Dreams Holidaze is on Saturday, November 21, 2026, 7 pm at Saenger Theatre. Confirm on the host’s page before you go.
How much is Elf Parade & Christmas Jubilee in Pensacola?
Free. Elf Parade & Christmas Jubilee is on Friday, November 27, 2026, 2 pm at Winterfest Plaza. Confirm on the host’s page before you go.
How much is Charles Dickens' A Christmas Carol in Pensacola?
Ticketed, see host page. Charles Dickens' A Christmas Carol is on Monday, November 30, 2026, 7:30 pm at Saenger Theatre. Confirm on the host’s page before you go.
How much is Saturday with Santa (Milton) in Milton?
Free. Saturday with Santa (Milton) is on Saturday, December 5, 2026, 10 to 11:30 am at Milton Library. Confirm on the host’s page before you go.
How much is Gingerbread House Competition in Pensacola?
Free. Gingerbread House Competition is on Saturday, December 12, 2026, 11 am to 2 pm at Studer Community Institute. Confirm on the host’s page before you go.
How much is Saturday with Santa (Gulf Breeze) in Gulf Breeze?
Free. Saturday with Santa (Gulf Breeze) is on Saturday, December 12, 2026, 10 to 11:30 am at Gulf Breeze Library. Confirm on the host’s page before you go.
How much is Ballet Pensacola's The Nutcracker in Pensacola?
Ticketed, see host page. Ballet Pensacola's The Nutcracker is on Fri December 18 (7 pm), Sat December 19 (1:30 to 7 pm) and Sun December 20 (1:30 pm), 2026 at Saenger Theatre. Confirm on the host’s page before you go.
How much is Saturday with Santa (Navarre) in Navarre?
Free. Saturday with Santa (Navarre) is on Saturday, December 19, 2026, 10 to 11:30 am at Navarre Library. Confirm on the host’s page before you go.
How much is Saturday with Santa (Pace) in Pace?
Free. Saturday with Santa (Pace) is on Saturday, December 19, 2026, 10 to 11:30 am at Pace Library. Confirm on the host’s page before you go.
Are there Christmas train rides for kids in Pensacola?
Yes, but they have their own guide. Santa trains and holiday train rides are listed in our Pensacola Christmas train rides guide, so this page sticks to story times, Santa visits and other events off the rails.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked every listing on November 2, 2026. Hosts change details, so always confirm on the host’s page before you go.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.
