Ho ho ho, the holiday spirit is high in Portland, Maine!
Buzzing with an array of exciting events that will fill your weekend with holiday cheer, this weekend you can enjoy enchanting holiday markets to heartwarming theater productions on a holiday classic. As we usher in the season of giving and gratitude, let’s explore the joyous happenings around town, including the enchanting “Christmas at Victoria Mansion,” the musical magic of “Magic of Christmas” with the Portland Symphony Orchestra, and so much more. Let this guide be your holiday compass to navigate the wonderland of events in Portland.
Here’s The Weekend Guide for Friday, December 8th – Sunday, December 10th, 2023
Friday the 8th
Christmas at Victoria Mansion | Victoria Mansion | 10:00 AM – 4:00 PM (Last entry as 3:00 PM), Tuesday – Sunday all December
Step into a holiday wonderland at Victoria Mansion! Embrace the magic of the season as top florists, designers, and artists transform this historic mansion into a Victorian-era spectacle. This beloved tradition, now in its fourth decade, invites you to explore the enchanting ‘Colors of the Season’ theme. Wander through rooms adorned with vibrant hues inspired by both the holiday spirit and the Mansion’s own opulent palette. Join for a self-paced tour from November 24, 2023, to January 7, 2024, and discover the timeless beauty of a Victorian Christmas. Tickets.
Felted Ornament Making | Toad & Co. | 6:00 PM – 8:00 PM
Learn how to make felted ornaments and celebrate the season with festive snacks and drinks! Toad & Co. is so excited to welcome Gaby Stratmann of bug-eyed co. to the shop for a felted ornament making workshop. Included in the workshop is 2 hours of instruction on the techniques and steps of needle felting, a ornament kit of your choice (either Busy Bees or Felted Garden), and festive refreshments and snacks. They will also be offering 30% off for participants in the retail space for holiday gift shopping. The ticket includes a felted ornament kit, foam felting block, as well as snacks and refreshments. Tickets.
Holiday Cocktail Class Vena’s Fizz House | Blind Tiger | 6:00 PM – 8:00 PM
Stir up some holiday magic with Vena’s Fizz House at Blind Tiger! Join for ‘The Class of Christmas Past,’ a delightful cocktail class that will turn even the biggest Scrooge into a festive fan. On the menu, they have two holiday-themed specials: the ‘Ebenezer Old Fashioned,’ a cherry-infused delight with hints of orange, and the ‘Tiny Tim Toddy,’ a cozy blend of ginger, cloves, and cinnamon. You can choose bourbon, rum, or apple cider for a mocktail twist! Plus, take home the secret ingredients to keep the holiday spirit alive with your own creations. Tickets.
A Christmas Carol | Portland Stage Co. | Multiple dates & times
Step into the holiday spirit with ‘A Christmas Carol’ at The Portland Stage Co.! Celebrate the season with this timeless tale of love, family, and the spirit of goodwill, beautifully brought to life on stage. Featuring charming costumes, delightful music, and a touch of ghostly magic, this enchanting production is a must-see for the whole family. Tickets.
Portland Symphony Orchestra Magic of Christmas | Merrill Auditorium | Multiple Dates & Times
Get ready for the 43rd year of holiday magic with Magic of Christmas! Join the Portland Symphony Orchestra for this cherished tradition, led by the talented Music Director Eckart Preu and featuring special guests. Let the spirit of the season fill your heart as they perform beloved Christmas classics, both timeless and new. And of course, don’t miss the enchanting ‘Sleigh Ride’! Tickets.
Vivid Motion Dance Presents: ‘Twas The Night Before… Burlesque | The Hills Art | 7:30 PM – 9:30 PM
Portland’s longest running burlesque tradition is back! Join Vivid Motion Dance for this year’s hot-hot-HOTTEST winter show, co-directed by Brigitte Paulus and MJ Emerson. In true innovative and quirky Vivid Motion Dance style, they have taken the classic holiday poem “Twas the Night Before Christmas” and turned it into a sizzling and sensual dance performance, complete with a live band onstage. Tickets.
Saturday the 9th
6th Annual Ugly Sweater Crawl | Fore Play – Registration | 4:00 PM – 10:00 PM
Deck the halls and don your ugliest sweater because it’s time for the 6th Annual Ugly Sweater Bar Crawl! Get into the holiday spirit with hundreds of merry-makers. Here’s how it all works: join the registration party and receive fantastic crawl swag, including an official lanyard; Follow your lanyard to five or more participating bars with fantastic drink deals; Dance to the tunes of their DJ entertainment and strike a pose for the photographer; and make it to the official after party and receive a holiday-themed giveaway. Complete the crawl and earn your bragging rights and a special giveaway at the after party. Will you crawl your way to holiday glory? Participating bars include Bonfire, Gritty’s, Dock Fore, Fore Play, Three Dollar Dewey’s and Citrus (official after party with DJ). Tickets.
Holiday Pop-Up Show | LB Kitchen | 4:00 PM – 8:00 PM
Get ready to sleigh the holiday season at LB Kitchen’s Holiday Mini-Market Extravaganza! Join for a festive bash featuring some of their favorite friends and makers. Sip on sparkly bubbles and wine tastings poured by Devenish Wines, while indulging in oysters from the legendary Lady Shuckers at the oyster bar. Enjoy peppermint lattes, both non-alcoholic and boozy, plus complimentary shopping popcorn. Discover the genius of celebrity blanket jacket maker, Cece and the Seams, and fall in love with the stunning jewelry creations of Big Feelings Jewelry. Illuminate your holiday with captivating scents from Candle Cowboy and sip your favorite drink from charming strawberry mugs courtesy of Ceramica Co. Shine bright with the creative brilliance of Mel Andrel, their guiding light for this incredible event. Expect disco lights, a giant wreath, and an all-around WILD time!
Pink Talking Fish | State Theatre | 8:00 PM
Pink Talking Fish is a musical phenomenon, a Hybrid Tribute Fusion Act that takes the music of three iconic bands – Pink Floyd, The Talking Heads, and Phish – and weaves them together into an extraordinary auditory journey. These bands aren’t just musical acts; they’re cultural phenomena that have inspired and connected people through their artistry and sensational live performances. Pink Talking Fish recognizes that although the music from each of these bands is distinct, combining them creates a mesmerizing narrative. It’s the emotional depth of Pink Floyd, the funky and danceable rhythms of The Talking Heads, and the eclectic styles, intricate compositions, and pure joy of Phish, all merged into a single remarkable experience for music enthusiasts. Tickets.
State Theatre Presents Pokey LaFarge | Portland House of Music & Events | 7:00 PM
Pokey LaFarge is an American Renaissance man — an acclaimed musician, writer, actor, and designer. Fusing the rustic sounds of the past with his wry humor and eclectic music sensibilities, singer/songwriter Pokey LaFarge is “an artful ambassador for old-time music, presenting and representing the glories of hot swing, early jazz, and ragtime blues.” (NPR’s Stephen Thompson) Over his 15-year career, Pokey has sold-out theaters worldwide; toured and recorded with Jack White. His music has been featured in TV shows like Boardwalk Empire and recently had a role in 2021’s Netflix movie Devil All the Time alongside Robert Pattinson and Tom Holland. Tickets.
Sunday the 10th
Cozy Winter Market | Congress Square Park | 11:00 AM – 3:00 PM
Warm up with the Friends of Congress Square Park as they host their first Cozy Winter Market! They will have all sorts of tasty treats, hot beverages, and locally made gifts for sale — plus fire pits to sit down and snuggle up around. Vendor line-up includes: Vagabond Coffee, Mellifluous Portland, The Challah Shoppe, MAIZ Colombian Street Food, Milk Bottle, Mount Cabot Maple, Kittylamb, Lucky Fox Bookshop, PineView Pottery, jbishop.design, R Nicole Studio and more!
Domingo Colombiano | Cocktail Mary | 2:00 PM
Join Cocktail Mary for DOMINGO COLOMBIANO!! Starting at 2pm, Isaac’s (Owner) mother in law, Elsy, will be serving her famous, homemade arepas. Calling in Love Cacao will also be here selling and sampling single origin cacao. And on top of that, they are launching their holiday drink menu!
Holiday Dash 5K | Eastern Prom Trail Portland | 11:00 AM
Join for Portland Trails’ annual, one-of-a-kind Holiday Dash 5K, presented by Martin’s Point Health Care! Whether you dress up in a winter-themed costume or keep things more traditional, this race along the Eastern Prom Trail is sure to warm your spirits. They will have hot cocoa waiting for you after you cross the finish line. The Holiday Dash 5K is Portland Trails’ largest fundraising event of the year. All proceeds from this race go toward maintaining and caring for the trails you love – all 75 miles of them. That’s why this year, you can fundraise for Portland Trails! Sign-up
Rasa String Quartet | One Longfellow Square | 7:00 PM – 10:00 PM
The Rasa String Quartet, hailing from Boston, masterfully blends classical and folk traditions. They are recipients of multiple prestigious awards and have collaborated with renowned folk musicians. As the 2022-23 ensemble in residence at Phillips Exeter Academy, their talent shines. Their program, titled “Strum,” showcases the art of strumming and includes works by Beethoven, Debussy, Turina, and contemporary composers like Jessie Montgomery and Caroline Shaw. This captivating performance explores the connection between music and storytelling, making it accessible and engaging for all audiences. Tickets.
For more events head to our Events Calendar here.