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There’s no denying it now, the holiday season is officially here and Portland is about to get extra festive this weekend!
After you’ve had your fill of turkey and pie, it’s time to dive into the season’s best events—holiday markets, twinkling lights, and unforgettable performances await. Picture yourself aboard the magical Polar Express, dancing to holiday tunes at Rock This Town’s Christmas Spectacular, or shopping local treasures at Definitive Brewing’s Holiday Market. From Monument Square’s Tree Lighting to cozy pop-ups and so much more, this weekend has everything you need to kick off the most wonderful time of the year!
Here’s The Thanksgiving Weekend Guide for Friday, November 29th – Sunday, December 1st, 2024
Friday the 29th
Monument Square Tree Lighting Ceremony | Monument Square | 1:00 PM Celebrations Start – Tree Lighting at 4:30 PM
Kick off the holiday season in style at the Monument Square Tree Lighting Ceremony! Starting at 1 PM, enjoy festive fun with live performances, ice carvings, a princess and superhero meet-and-greet, and a Frozen II watch party. Stick around for the grand ceremony at 4:30 PM, featuring Portland Ballet and a stunning performance by Julia Gagnon, American Idol Season 22 Top 7 finalist. Perfect way to sprinkle some holiday magic into your week.
Christmas at Victoria Mansion | Victoria Mansion | 10:00 PM – 4:00 PM (Tuesday – Sunday through January 5th)
Step into a world of Victorian-era splendor at Christmas at Victoria Mansion, running from November 29th, 2024, to January 5th, 2025. This year’s theme, Stories of the Season, transforms the Mansion into a storytelling wonderland, with designers drawing inspiration from classic 19th-century holiday tales and regional folklore. Tours every half hour from 10 AM to 4 PM (final admission 3 PM), this annual event is a feast for the eyes and the imagination. An enchanting tradition that brings history, art, and holiday cheer together! Tickets.
Holiday Joy Craft Fair | coworkHERS | 12:00 PM – 4:00 PM through December 23rd
Get ready to shop, snack, and celebrate at the Holiday Joy Craft Fair at coworkHERS! Running through December 23rd, this festive pop-up features a fabulous mix of art, music, and delicious bites—all within a coworking space dedicated to empowering women and fostering inclusion. It’s the perfect spot to find unique, handcrafted gifts while soaking in the holiday spirit. Don’t miss your chance to support local makers and leave with something truly special!
Maine State Ballet’s The Nutcracker | Merrill Auditorium | 2:00 PM (Repeats Saturday and December 1st, 7th, 8th)
The magic of the holiday season comes to life with Maine State Ballet’s enchanting production of The Nutcracker, running from November 29th to December 8th at Merrill Auditorium. Under the direction of Artistic Director Linda MacArthur Miele, this beloved classic tells the story of Clara and her Nutcracker Prince as they journey through the whimsical Land of Sweets. With stunning costumes and scenery by Gail Csoboth and live music from the Maine State Ballet Orchestra, this performance is sure to be a festive highlight for the whole family. Experience the wonder of the season! Tickets.
Rock This Town – Rockabilly Riot | One Longfellow Square | 8:00 PM
Come celebrate the holiday season with Rock This Town Orchestra’s Christmas Spectacular! This high-energy show brings together the best of 50s and 60s rockabilly hits with your favorite Christmas classics. From “Rock This Town” to “Jingle Bells”, expect a night of toe-tapping tunes and festive fun that will have you dancing in your seats all night long. With its visually stunning performances and electrifying atmosphere, this holiday extravaganza is one you’d be upset to miss. An unforgettable night of music and holiday cheer! Tickets.
The Polar Express Train | Maine Narrow Gauge | 2:45 PM, 4:00 PM, 5:15 PM, 6:30 PM, 7:45 PM (Multiple Dates & Times)
All aboard the Polar Express™ Train Ride—a magical holiday tradition! Starting November 29th, hop on at Portland’s Ocean Gateway Marine Terminal for a journey to the North Pole. This beloved experience, with over 23,000 passengers last year, offers live actors, hot cocoa, cookies, and a special visit from Santa himself, who hands out the first gift of Christmas. Enjoy festive music and the warmth of the steam locomotive as you head to the North Pole, and make memories that’ll last a lifetime. This event is the Maine Narrow Gauge Railroad’s largest fundraiser, supporting its mission and bringing holiday magic to families. Tickets.
Saturday the 30th
SPACE Pop-Up Shop | SPACE | Thursdays – Saturdays through December 20th
Shop local and support the arts at the SPACE Pop-Up Shop, open now through December 20th! Curated by the team at SPACE, this festive pop-up is packed with one-of-a-kind items from independent artists, including books, records, prints, clothes, and more. Whether you’re on the hunt for the perfect gift or a special treat for yourself, you’ll find something unique that supports creative talent close to home. Stop by the 534 Gallery Thursday through Saturday starting at noon.
Small Business Saturday Market | Fork Food Lab – South Portland | 10:00 AM – 1:00 PM
Kick off your holiday shopping with a big dose of Maine-made goodness at the Small Business Saturday Market at Fork Food Lab! This is your chance to support local food entrepreneurs and makers who are crafting some of the finest products in the state. With a lineup of talented vendors like Black Salt Dining, Cambodia’s Best and Electric Oven Bakes, you’re sure to find unique gifts (and delicious treats) to check off your list. Tickets are just $6, with all proceeds benefiting Fork Food Lab, so you can shop small and give back at the same time. Tickets.
Model Airplane – Funksgiving | Aura | 8:00 PM
The ultimate Thanksgiving weekend celebration! Taking over the stage with their signature blend of R&B, soul, and funk, this high-energy show is led by none other than the incredible Lyle Divinsky. Model Airplane, known for their legendary funk performances, this year’s Funksgiving is sure to get you moving as the band delivers two sets of groove-packed classics that’ll have you dancing all night long. It’s the perfect way to work off your Thanksgiving feast— Funksgiving is the party that never stops! Come ready to party! 18+ only. Tickets.
Rock out this holiday weekend with Rigometrics at their annual Rigsgiving celebration! Known for their high-energy, genre-blending sound, this Portland-based trio is set to blow the roof off with explosive guitar solos, pounding beats, and jaw-dropping vocals. Josef Berger shreds through electrifying melodies, while Derek Haney lays down the groove with his pulsating drums, and Keenan Hendricks hits soaring vocal ranges, all paired with hammering piano skills. This unforgettable night of rock ‘n’ roll is not to be missed— get ready for a serious sonic celebration! Tickets.
TimeMachine The Reunion Maine | Bar Publica | 8:00 PM
Get ready to rewind the clock and groove to the best of the past at TimeMachine The Reunion at Bar Publica! Starting at 8 PM, DJ duo Dale Da Dred and B.Aull will be spinning all the hits from the 80s, 90s, and 2000s, bringing those nostalgic vibes that’ll have you dancing all night long. This throwback party is the perfect way to relive the magic of those iconic decades. Tickets.
Comfort and Joy: Christmas in Olde New England | Maine Historical Society | 11:00 AM, 1:00 PM, 2:00 PM, 3:00 PM (Repeats December 7th, 14th, 21st)
Step back in time and immerse yourself in the cozy charm of a 19th-century New England Christmas! This holiday season, take a guided tour through the beautifully decorated Wadsworth-Longfellow House, showcasing the festive traditions of the Longfellow family. Learn about the delicious treats they enjoyed, the Christmas Eve rituals they observed, and the games and songs that filled their home with joy. With small, intimate tours limited to 12 guests, you’ll feel like you’re part of the family. Plus, enjoy a 10% discount at the Museum Shop, perfect for finding unique gifts! Tickets.
Sunday the 1st![]()
Mr. Sun Plays Ellington’s Nutcracker | One Longfellow Square | 6:00 PM
A fresh take on a holiday classic when Mr. Sun performs Ellington’s Nutcracker at this special show! This inventive reimagining of Tchaikovsky’s timeless suite blends the original melodies with the rich sound of an American String Band. Drawing inspiration from Duke Ellington’s iconic jazz rendition, Mr. Sun’s performance mixes close renditions of Billy Strayhorn’s original charts with bold improvisations, adding new flavors like Bluegrass and Dawg Music. With guests like Alison Brown on banjo and Jerry Douglas on dobro, this performance will have you experiencing The Nutcracker like never before—sophisticated, festive, and full of surprises. Tickets.
Spencer and the Walrus present Beatles Night 3 Family Matinee | State Theatre | 3:00 PM (Friday & Saturday @ 8:00 PM)
Gather the whole family for Spencer and the Walrus’ Beatles Night Family Matinee, where the iconic tunes of the Fab Four come to life in a rockin’ live performance! This all-ages show is the perfect opportunity for the whole family to experience the timeless classics of the Beatles—Hey Jude, Come Together, All You Need Is Love, and more—performed live by a talented ensemble of Portland musicians. No wigs, no accents—just the raw energy of the Beatles’ music, from Twist and Shout to Let It Be. Best of all, $1 from each ticket goes to support local youth music programs, making this a show you can feel good about. Tickets.
Holiday Market | Definitive Brewing Co. | 1:00 PM – 6:00 PM
Unwrap the magic of the season at Definitive Brewing! Join for a rotating lineup of talented makers, artisans, and artists showcasing their locally crafted goods. From pottery and art to jewelry, candles, home goods, and more, there’s something special for everyone on your list. Come sip a pint, shop local, and support Maine’s creative community this season! Visit at definitivebrewing.com/calendar for more info and to see what vendors to expect!
For more events head to our Events Calendar here.
