Special Issues » Holiday Guide

Holiday fun in Orlando for 2021's festive season

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The holly, the jolly, the tinsel and the turkey, the menorah and the kinara of it all.

Through Nov. 21
Festival of Trees
Orlando Museum of Art, 2416 N. Mills Ave., $20, omart.org.

Through Dec. 18
Christmas My Way: A Sinatra Holiday Bash
From classic Sinatra tunes to seasonal favorites Rat Pack Style, catch 40 popular hits including "The Christmas Song," "Silver Bells," "I'll Be Home for Christmas" and more. Winter Park Playhouse, 711 Orange Ave., Winter Park, $36-$45, winterparkplayhouse.org.

Nov. 17-Dec. 19
Rodgers and Hammerstein's Cinderella
A contemporary take on the classic tale features Rodgers & Hammerstein songs alongside an up-to-date, hilarious and romantic libretto by Tony Award nominee Douglas Carter Beane. Orlando Repertory Theater, 1001 E. Princeton St., $15-$35, orlandorep.com.

Nov. 19-Jan. 9, 2022
Dazzling Nights
Experience an immersive holiday light experience. Harry P. Leu Gardens, 1920 N. Forest Ave, $25, leugardens.org.

Saturday, Nov. 20
Breakfast With Santa
A morning of making memories with Santa Claus with exclusive access to the 35th Annual Festival of Trees before it opens to the public during the day. Breakfast with Santa will feature hot breakfast served to everyone, face-painters, crafts, balloon artists and more. 8:30 a.m. Orlando Museum of Art, 2416 N. Mills Ave, $35, councilof101.org.

MACY'S DAY PARADE AT UNIVERSAL
  • Macy's Day Parade at Universal

Saturday-Sunday, Nov. 20-21
Fall Festival of the Arts
See work from more than 150 fine artists from all over the U.S., plus musical entertainment both days, youth art on display, hands-on art-making opportunities for the kids and even poetry in the park. Downtown DeLand, Indiana Avenue and South Woodland Boulevard, free, fallfestivaloftheartsdeland.com.

Saturday, Nov. 20
Holly Jolly Market
Shop from more than 20 vendors. Be sure to shop local and small this holiday season! 1-6 p.m. Orlando Brewing, 1301 Atlanta Ave, free.

Saturday, Nov. 20
Jingle Eve
This event includes a children's Holiday Village in Gaston Edwards Park along with a stage and unique vendors, 12 Wines of Christmas wine walk, music throughout the district, food trucks, vendors lining Orange Avenue and Virginia Drive, and a highly festive atmosphere. 4-10 p.m. Gaston Edwards Park, 1236 N. Orange Ave., free, ivanhoevillage.org.

Saturday-Sunday, Nov. 20-21
Longwood Arts and Crafts Festival
Over 200 original artisans and crafters selling unique items. Historic Downtown Longwood, West State Road 434 and South County Road 427, free, longwoodfestival.com.

Sunday, Nov. 21
Latin Jazz Brunch
The Jazz Orchestra at Dr. Phillips Center Octet, led by internationally renowned bassist Rodney Whitaker and founded with the support of Jazz at Lincoln Center. Brunch optional. 1 p.m. Frontyard Festival, 445 S. Magnolia Ave, $25-$60, drphillipscenter.org.

Wednesday, Nov. 24
Thanksgiving Eve Pub Crawl
6 p.m. The Milk District Spot, 2430 E. Robinson St., $10, eventbrite.com.

Nov. 25-Dec. 26
The Lights at Jeater Bend
A stunning light display on 11 Celebration homes collects donations and canned food for local families in need. Jeater Bend Drive, Celebration, facebook.com/lightsonjeaterbend, free/donation.

Saturday-Sunday, Nov. 27-28
FusionFest
A free two-day celebration in downtown Orlando featuring a kaleidoscopic fusion of aromas, sights, sounds and tastes that represent the diverse origins and heritages of our community. Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, free, fusionfest.org.

Saturday, Nov. 27
Home for the Holidays
With the Orlando Philharmonic Orchestra. 3:30 p.m. Orlando Festival Park, East Robinson Street and North Primrose Drive, $40, orlandophil.org.

Sunday, Nov. 28
Sanford Holiday Mini Indie Market
11 a.m. Tuffy's Bottleshop and Lounge, 200 Myrtle Ave., Sanford, free, tuffyscider.com.

Sunday, Nov. 28
Chanukah on the Park
The event will include an art acrobat show, live music, dancers, kids activities, jugglers, food and grand menorah lighting. 5 p.m. Central Park, Winter Park, North Park Avenue and West Morse Boulevard, Winter Park, free, chabadorlando.org.

A DRAG QUEEN CHRISTMAS
  • A Drag Queen Christmas

Tuesday, Nov. 30
2nd Annual Lake Nona Chanukah Celebration
Join us as we light the menorah and celebrate the festival of Chanukah among friends and family. Grand menorah lighting, sufganiyot, face painting, Jewish music, activities for kids and much more! 5:30 p.m. Lake Nona Town Center, 6900 Tavistock Lakes Blvd., free.

Dec. 1-24
A Christmas Carol
The miserly and miserable Ebenezer Scrooge greets each Christmas with a "bah humbug," until he is visited by the Ghosts of Christmas Past, Present, and Yet to Come. Margeson Theater, Lowndes Shakespeare Center, 812 E. Rollins St., $32-$56.

Wednesday, Dec. 1
Gary Gulman
Gulman's most recent stand-up special for HBO, The Great Depresh, is a tour-de-force look at mental illness, equal parts hilarious and inspiring. 7 p.m. Alexis & Jim Pugh Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, $35, drphillipscenter.org.

Dec. 2-30
Pippin
Centered around the tale of Roman Emperor Charlemagne's first son and set in an ecstatic world of music, magic and sensuality. Mad Cow Theatre, 54 W. Church St., $20-$53, madcowtheatre.com.

Thursday, Dec. 2
1st Thursdays: Within These Walls
Featuring work by museum personnel, the exhibition is a combination of the creative forces that reflect the diversity of the Orlando Museum of Art's community. 6 p.m. Orlando Museum of Art, 2416 N. Mills Ave, $15, omart.org.

Thursday, Dec. 2
Christmas in the Park
The Morse Museum helps launch the holiday season in Winter Park when it lights up Tiffany windows in Central Park and presents the Bach Festival Choir and Brass Ensemble in concert. Held in the northern section of Central Park near the intersection of Garfield and Park avenues. 6:15-8:30 p.m. Central Park, North Park Avenue and West Morse Boulevard, Winter Park, free.

Friday, Dec. 3
Annual Tree Lighting Celebration
The city of Orlando celebrates the first official lighting of the 64-foot Wonderland Christmas tree located at Lake Eola's Park Washington Plaza. The event will include holiday performances at the Walt Disney Amphitheater, food trucks, a holiday market and an opportunity to meet Santa until 9 p.m. at the Eola House. 5 p.m. Walt Disney Amphitheater, Lake Eola Park, Rosalind Avenue and Washington Street, free.

Friday, Dec. 3
Phantasmagoria's "A Christmas Carol, A Ghost Story of Christmas"
Dickens' tale of the Past, Present and Future — with the glory of redemption. The Victorian performance troupe will bring its signature tapestry of movement, dance, puppetry, projections and storytelling to the stage. 8 p.m. Alexis & Jim Pugh Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, $36.70, drphillipscenter.org.

Friday, Dec. 3
Songs of the Season
The community is invited to share in an evening of song, dance and entertainment, including a chance to sing along with holiday favorites like "Jingle Bells" and "Silent Night." 7 p.m. Frontyard Festival, 445 S. Magnolia Ave, $14.75, drphillipscenter.org.

Saturday, Dec. 4
69th Annual Winter Park "Ye Olde Hometown" Christmas Parade
The parade will travel south along Park Avenue, turn west on New England Avenue and end at the Winter Park Community Center. 9 a.m. Central Park, North Park Avenue and West Morse Boulevard, Winter Park, free.

Saturday, Dec. 4
Christmas Vespers
This beautiful, candlelit service is a Rollins tradition with a rich history that stretches back to 1933. An elegant candlelit procession is followed by student-performed Christmas carols as well as scripture readings that reflect on the season. 6 p.m. Knowles Memorial Chapel, Rollins College, 1000 Holt Ave. Winter Park, price TBA.

Saturday, Dec. 4
Collective Corner Pop-up Market
Sixty-plus vendors offering an array of locally made goods, vintage home decor, furniture, plants and many more curated items. 11 a.m.-4 p.m. Blue Jacket Park, 2501 General Rees Ave, free, instagram.com/collectivecornerflorida.

Saturday, Dec. 4
DeLand Christmas Parade
5:30 p.m. Downtown DeLand, Indiana Avenue and South Woodland Boulevard, free.

Dec. 4-Jan. 6, 2022
Eola Wonderland Christmas Tree Show
Every night at 5:45 p.m., 6:45 p.m., 7:45 p.m., 8:45 p.m. and 9:45 p.m., the 64-foot tree will come alive with a synchronized light and music show while the Lake Eola fountain displays red, green and gold lights. Lake Eola Park, Rosalind Avenue and Washington Street, free.

Saturday, Dec. 4
Holiday Market at Back to Nature
Shop unique gifts and enjoy delicious food from our local craft and food vendors. Take your own photos with Santa Claus and the Grinch inside Santa's Enchanted Forest and enjoy story time with Mrs. Claus and her woodland friends. Kids activities include crafts, face painting and wildlife encounters. 11 a.m.-4 p.m. Back to Nature Wildlife Refuge, 10525 Clapp Simms Duda Road, free-$5, btnwildlife.org/events.

Saturday, Dec. 4
Holly Jolly Sounds of the Season
Join members from the brass and percussion families for a musical celebration that will capture the spirit of the season. Orlando Philharmonic Orchestra musicians will play holiday classics from "Frosty the Snowman" to "Rudolph the Red-Nosed Reindeer." 10 & 11:30 a.m. The Plaza Live, 425 N. Bumby Ave, $10, plazaliveorlando.org.

Saturday, Dec. 4
Jazz at Lincoln Center Jazz Orchestra with Wynton Marsalis
It's the most wonderful time of year courtesy of the Jazz at Lincoln Center Orchestra with Wynton Marsalis. This big band holiday show features soulful versions of classics like "Jingle Bells," "Joy to the World" and "Brazilian Sleigh Ride." 7:30 p.m. Frontyard Festival, 445 S. Magnolia Ave, $40-$80, drphillipscenter.org.

Saturday, Dec. 4
Jingle Jam Community Holiday Party
Featuring four stages of live music, food trucks, carnival games, holiday artisanal vendors, live wrestling, a kids zone and more. See Santa himself, take pictures with him and enjoy storytime. 4 p.m. Downtown Sanford, Sanford Avenue and First Street, free.

Saturday, Dec. 4
Longwood Christmas Parade
3 p.m. Historic Downtown Longwood, West State Road 434 and South County Road 427, free.

Saturday, Dec. 4
The Nutcracker – Family & Sensory Friendly Show
During this one-hour version of the annual favorite, journey to a world of fantasy and fun complete with the Mouse King, Sugar Plum Fairy and Mother Ginger. This performance is specially designed for families of all ages. Expect a welcoming, supportive environment for people of all abilities. Adjustments to sound and lighting effects, including keeping the house lights dimly on, will be made. For families with individuals with special needs, find out more about Dr. Phillips Center's designation as a Certified Autism Center. 11 a.m. Walt Disney Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, $24-$104, drphillipscenter.org.

Saturday, Dec. 4,
The Nutcracker
With Russian Ballet Orlando and Orlando Philharmonic Orchestra. 2 & 7 p.m. Ritz Theater Sanford at the Wayne Densch Performing Arts Center, 201 S. Magnolia Ave., Sanford, $40-$55, ritztheatersanford.com.

Saturday-Sunday, Dec. 4-5
43rd Annual Cracker Christmas
History! Fort Christmas Historical Park, 1300 Fort Christmas Road, Christmas, free, orangecountyfl.net.

Sunday, Dec. 5
DeLand Indie Market Holiday Edition
Over 70 vendors, live music, food and fun. 11 a.m. Artisan Alley, Artisan Alley, DeLand, free.

Sunday, Dec. 5
Krampusfest
Oh, now you're in BIG trouble. 1 p.m. The Plaza Live, 425 N. Bumby Ave., free, eventbrite.com

Sunday, Dec. 5
Holiday Pops in Winter Park
Bring your blanket and a picnic for a concert program of holiday favorites performed by Orlando Philharmonic Orchestra. 5 p.m. Central Park, North Park Avenue and West Morse Boulevard, Winter Park, free.

Sunday, Dec. 5
Light Up SoDo
Get ready for face painting, letters to Santa, stilt-walkers, train rides, princesses, bounce houses, a visit from Santa and Mrs. Claus and live performances. 2 p.m. SoDo District, 503 W. Grant St., free-$5.

Tuesday, Dec. 7
Many Moods of Christmas
Featuring the Bethune Cookman University Concert Chorale, this evening features a myriad of classic holiday tunes including soul-stirring gospel favorites, jazz, soul, spirituals and impactful music by African American composers. 6 p.m. Frontyard Festival, 445 S. Magnolia Ave, free, drphillipscenter.org.

Thursday, Dec. 9
Griswold Family Sip & Shop
A night of holiday shopping from local vendors hosted by the Griswold Family. Movie begins at 7:30 p.m., free reserved seating is available. 6:30 p.m. Grape & the Grain, 1110 Virginia Drive, free.

Thursday, Dec. 9
A Holiday Homecoming
The Central Florida Community Choir, members of the CFCArts Symphony Orchestra, as well as the CFCArts Dance Company return to their holiday roots. 7:30 p.m. Northland Church, Room 4210, Longwood, $10-$50.

Friday, Dec. 10
The 12 Bars of Christmas Pub Crawl
Step 1: Register for the event. Step 2: Bring a new, unwrapped toy valued at a minimum of $20 or $20 cash for admission to the event. Step 3: Get dressed up in all of your favorite holiday gear from Santa hats to ugly sweaters and crawl through 12 downtown bars! Meet up at 8 p.m. at Hooch, 25 Wall St., $20, eventbrite.

Dec. 10-19
Holiday on Church Street
Get ready to soak up that much-needed holiday spirit with food, fun and live entertainment. Pick from six dates to start celebrating the most wonderful time of the year. 7 p.m. Fridays, Saturdays. Mad Cow Theatre, 54 W. Church St., $30, 407-297-8788, madcowtheatre.com.

Saturday, Dec. 11
Christmas Pub Crawl Orlando
We're barhopping all day and night from 2 p.m. until 2 a.m. Expect hundreds of attendees and lots of drink specials! 2 p.m. Location TBA, $5, eventbrite.

Saturday, Dec. 11
Holiday on the Drive
Edgewater Drive is alive and full of holiday spirit at this much-loved annual family event. Edgewater Drive and Smith Street, free.

Saturday, Dec. 11
Sanford Parade of Lights
6 p.m. Downtown Sanford, Sanford Avenue and First Street, free.

Saturday, Dec. 11
A Spectacular Christmas
Join the cast as they travel through the magical journey of winter, toys, candy and much more to reach their final destination of finding the true meaning of Christmas. 5 p.m. Alexis & Jim Pugh Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, $25, drphillipscenter.org.

Saturday, Dec. 11
Violectric Holiday Show
Traditional holiday songs like "O Christmas Tree," "The First Noel" and "Hanukkah, O Hanukkah" are mashed up with classic rock tunes and modern hits like "Born to Run," "Heroes" and "Sweet Dreams," delivering a fun-filled, energetic and highly unique holiday show unlike anything seen and heard before. 7 p.m. Walt Disney Amphitheater, Lake Eola Park, Rosalind Avenue and Washington Street, free.

Saturday, Dec. 11
A Vivacity Christmas
Featuring xylophonist Heather Thorn and Australian/NYC-based saxophonist Adrian Cunningham, Vivacity brings you beloved holiday classics for all ages. 4 & 7 p.m. Timucua Arts Foundation, 2000 S. Summerlin Ave, $30-$50, timucua.com.

Saturday, Dec. 11
Winter Park Holiday Boat Parade
Live viewing at Dinky Dock Park on Lake Virginia. 6:30 p.m. Dinky Dock Park, Ollie Avenue, Winter Park, free.

Sunday, Dec. 12
A Classic Christmas
A Central Florida holiday tradition, this program features beloved Christmas and seasonal gems performed by the renowned Bach Festival Choir and Orchestra with soprano Mary Wilson and Grammy award–winning bass-baritone Dashon Burton. 7 p.m. Frontyard Festival, 445 S. Magnolia Ave, $35-$95, drphillipscenter.org.

Sunday, Dec. 12
Grandma Party Bazaar
Local vendors and local makers peddle gifts for those inscrutable friends and family members. 10 a.m. Stardust Video and Coffee, 1842 E. Winter Park Road, free, facebook.com/stardustie.

Monday, Dec. 13
Holiday Baroque with Rimma
Rimma Bergeron-Langlois, violin and conductor; Diane Bishop, bassoon; Colleen Blagov, flute; and Jamie Strefeler, oboe, play Vivaldi, J.S. Bach, Albinoni and Torelli. 7 p.m. The Plaza Live, 425 N. Bumby Ave, $18-$54, plazaliveorlando.org.

Tuesday, Dec. 14
Ginger Minj's Winter Wonderland
A nondenominational musical romp through the holidays with Ginger Minj and Gidget Galore! 8 p.m. The Abbey, 100 S. Eola Drive, $25-$40, abbeyorlando.com.

Wednesday, Dec. 15
Golden Gals Live: Cheesecake and Cheer
Blanche, Rose, Dorothy and Sophia deck the halls with cheesecake and cheer. 8 p.m. The Abbey, 100 S. Eola Drive, $25-$35, abbeyorlando.com.

Thursday-Saturday, Dec. 16-18
Tushin' Through the Snow
Tymisha "Tush" Harris kicks off a brand-new outdoor cabaret series with a holiday performance. Tickets sold as tables for two. Darden Courtyard, Lowndes Shakespeare Center, 812 E. Rollins., $60, orlandoshakes.org.

Friday-Sunday, Dec. 17-19
Holiday Matsuri 2021
Holiday Matsuri is a festively themed anime, gaming and cosplay convention with holiday cheer. Marriott Orlando World Center, 8701 World Center Drive, free-$700, holidaymatsuri.com.

Saturday, Dec. 18
The Nutcracker
With Russian Ballet Orlando and Orlando Philharmonic Orchestra. 7:30 p.m. Walt Disney Amphitheater, Lake Eola Park, Rosalind Avenue and Washington Street, free-$25.

Tuesday, Dec. 21
Clara's Christmas Adventure
The Skyra Foundation presents a full-length production of the holiday classic The Nutcracker including a dazzling winter wonderland with a snowfall on stage. 2 & 7 p.m. Alexis & Jim Pugh Theater, Dr. Phillips Center for the Performing Arts, 445 S. Magnolia Ave, $29-$39, drphillipscenter.org.

Friday, Dec. 24
Christmas Eve Celebration
Enjoy free admission to the Morse Museum galleries between 9:30 a.m. and 8 p.m. with live violin music from 1-4 p.m. Charles Hosmer Morse Museum of American Art, 445 N. Park Ave., Winter Park, free, morsemuseum.org.

Sunday, Dec. 26
Central Florida's Kwanzaa Celebration Day 1: Umoja/Unity
Join us at the Winter Park Community Center for the day-long celebration of Umoja and the principle of unity! Enjoy a drum circle, dancing, performances, food provided by Flava Tribe, plus ancestor veneration to honor those loved ones that are no longer with us. 5 p.m. Winter Park Community Center, 721 New England Ave., Winter Park, $5.

Sunday, Dec. 26
A Drag Queen Christmas
Hosted by Trinity The Tuck & Monet X Change, with performances by Kylie Sonique Love, Jaida Essence Hall, Crystal Methyd, Brooke Lynn Hytes, Heidi N Closet and Willam. 8 p.m. The Plaza Live, 425 N. Bumby Ave., $50-$150, plazaliveorlando.org.

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