The holiday season is in full swing and Portland’s got a line-up of festive events that’ll make you feel like the season’s greetings have come alive!
This weekend, get ready to shop local and support Maine’s talented artisans at events like the Caravan Artisan Market at Allagash Brewing and the Boozy Book Far at Novel. Whether you’re exploring the charming Old Port Holiday Historic Walking Tour, enjoying a creative evening at the Friends & Family Pizza and Pottery event, or catching the magical Let It Glow tree lighting at The Porthole, there’s enough holiday spirit going around for everyone to enjoy. Deck the halls and make this weekend one for the books!
Here’s the Weekend Guide for Friday, December 6th – Sunday, December 8th, 2024
Friday the 6th
Copper Beech Tree Lighting | Portland Museum of Art | 6:00 PM
Photography by Molly Haley, mollyhaley.com
Get into the holiday spirit at the Portland Museum of Art’s annual Copper Beech Tree Lighting! The festivities kick off at 6 PM with music by 317 Main Community Choir, poetry from The Telling Room, and sweet treats courtesy of B+B Bakery. Warm up inside the museum and explore As We Are, Peggy Bacon: Biting, Never Bitter, and more—all free until 8 PM. A perfect night of holiday cheer awaits!
Boozy Book Fair | Novel | 5:00 PM – 9:00 PM
‘Tis the season for books and booze! Join Novel – Portland’s book bar and cafe for their festive Boozy Book Fair, hosted alongside Back Cove Books, Greenhand Books, and Coast City Comics. They’ll have a curated selection of books, gift items, and merch to make your holiday shopping extra special. Plus, enjoy a drink while you shop and discover the perfect read (or gift) to get you in the holiday spirit!
Music History Fest | SPACE | 5:00 PM – 8:00 PM
Celebrate the relaunch of Screed Magazine with the Music History Fest at SPACE during the First Friday Art Walk. This free, all-ages event is a dream for music lovers, featuring karaoke, zine-making, and an exhibit from Maine Punk showcasing artifacts from Maine’s punk history. Dive into interactive activities like surveys, community idea walls, and art-making to help shape Screed’s next issue. Wear your favorite band tee—or go all-out in musical cosplay—to score a free copy of their latest release. Come for the nostalgia, stay for the creative energy!
The Rainbow Affair and After Party | Maine Studio Works | 5:00 PM
Get ready to sleigh at The Holiday Rainbow Affair & After Party benefitting Equality Community Center. Happening at the Maine Studio Works, this fabulous celebration is back with a winter holiday twist, featuring food from Black Betty’s Bistro, drinks by Sagamore Hill, and live entertainment that’ll have you jingling all the way. Stick around for the after-party with beats from DJ Liz Rhaney and a dazzling performance by Tasha Tektite. It’s the ultimate night to don your gay apparel and celebrate the season in style! Tickets.
UNWRAPPED: Holiday Burlesque | Sacred Profane Brewing | 7:00 PM
Unwrap some holiday cheer with THEM Burlesque! This dazzling evening of glitz, glamour, and festive fun brings a lineup of stunning performers ready to heat up the season with their teasing tunes and captivating moves. Hosted by the jolly Timmy Elliott as Santa, the stage will light up with stars like Rosie Havoc, Poletoria, Fabergé, and more. Grab a drink, some food, and a seat—you won’t want to miss this unforgettable holiday spectacle! Tickets.
State Theatre Presents The Masterstroke Queen Experience | PHOME | 8:00 PM
Is this the real life? Is this just fantasy? Relive the glory of Queen as this electrifying tribute rocks you with iconic hits like Bohemian Rhapsody, We Will Rock You, and Don’t Stop Me Now. From their anthems to their legendary ballads, it’s a killer Queen experience you won’t want to miss. So, break free, and join PHOME and The Masterstroke Queen Experience for a night that will have you screaming, “We are the champions!” Tickets.
Indigo Poppin’ Dance Party | The Jewel Box | 10:00 PM
Get ready to groove, because Indigo Arts Alliance is bringing the vibes to The Jewel Box for their annual Indigo Poppin’ Dance Party! This year’s theme? Y2K fabulousness—think Bratz Dolls, Destiny’s Child, and brat summer all rolled into one unforgettable night. Join Friday, December 6th, from 10 PM to 1 AM, with DJ Ben Spalding (2022 Fall David C. Driskell Fellow) spinning the tracks that’ll keep you moving. Suggested $5 cover goes straight to supporting Indigo Arts Alliance’s mission of Art + Activism. Dance into the holiday season in style!
Saturday the 7th
Odd Fellows Holiday Craft Bazaar | 651 Forest Ave | 10:00 AM – 3:00 PM
Holiday magic at the Odd Fellows Holiday Bazaar! On Saturday, Woodfords Corner transforms into a festive haven with 30 local artists showcasing their amazing creations. Make a day of it in Woodfords Corner! Find thoughtful gifts and maybe snag something special just for you! While you’re there, grab a Woodfords Weekend Bingo Card and explore the neighborhood. Visit any of the 25 participating businesses to complete a bingo and enter to win fabulous prizes from local shops.
Old Port Holiday Historic Walking Tour | Monument Square | 11:00 AM – 1:30 PM (Multiple Dates)
Discover the holiday magic and rich history of Portland’s Old Port on this festive 2 ½ hour, 2-mile guided walking tour! Starting at Monument Square by the city’s official holiday tree, you’ll learn about the origins of Christmas trees and America’s first Christmas. Along the way, explore over 50 historic stops, visit the iconic Lobster Trap Tree, hear the tale of Charles Dickens’ unusual Portland visit, and end outside Henry Wadsworth Longfellow’s home with the story of his poem Christmas Bells. Reserve.
Winnie-the-Pooh | The Children’s Museum & Theatre of Maine | December 7h – 29th
Step into the Hundred Acre Wood with Winnie-the-Pooh, adapted by Sean Patrick Nill from the beloved tales by A.A. Milne. In this heartwarming production, Christopher Robin adjusts to life in London after leaving his countryside home, feeling lonely and uninterested in making new friends. But with the help of his father’s imaginative stories about a lovable bear and his forest friends, Christopher Robin discovers the magic of play, friendship, and new beginnings. Perfect for audiences of all ages, this charming adaptation brings the timeless adventures of Pooh, Piglet, and the gang to life on stage. Don’t miss this delightful journey into a world of wonder and whimsy! Reserve.
After ten amazing years, SLAB closed its doors this past fall, but they’re back for one last hurrah! Join this Saturday at Leisure Cocktail Co. for a special pop-up with Sauce and Destroy at 2pm until sellout. Enjoy three delicious topping options, all featuring the legendary Sauce and Destroy pizza sauce. Don’t miss your chance to taste this epic collaboration before it’s gone!
Portland Winter Farmers’ Market | 631 Stevens Avenue | 9:00 AM – 1:00 PM
Portland Indoor Farmers’ Winter Market is returning to 631 Stevens Avenue in Portland this weekend! Open every Saturday from 9 AM – 1 PM through April 12, 2025, this market is your go-to spot for fresh local produce and winter essentials. With over 20 Maine farmers and artisans, you’ll find everything from fresh greens, eggs, and meats to baked goods, jams, and even oysters. Enjoy live music, easy parking, and SNAP/EBT benefits doubled at the Market Info Booth. Plus, pick up unique items like market tote bags and aprons, join the Friends of the Market, or take a chance at winning monthly gift certificate raffles.
Let It Glow: Lobster Tree Lighting Celebration | The Porthole | 6:00 PM
A holiday season packed with festive cheer at The Porthole! Join on Portland’s Biggest Deck for the annual Let It Glow Lobster Tree Lighting Celebration, starting at 6 PM – complete with a boozy hot chocolate bar! Before the tree shines bright, make sure to visit the Holiday Maker’s Market, featuring live music by Andi Fawcett, and unique local finds. And don’t forget, the fun kicks off earlier that day with Santacon in Portland at 4 PM. Come for the lights, stay for the laughter, and enjoy the best of the season with The Porthole!
Sunday the 8th![]()
SIDEWORK Artist Market Sunday | 685 Congress Street | 1:00 PM – 5:00 PM
Join for the 7th annual SIDEWORK Artist Market at Big Tree Hospitality’s new full-time space at 685 Congress Street, the former Local 188 location! This exciting new venue means they can host more vendors than ever before, making it the perfect place to find unique holiday gifts. Enjoy food, drinks, and a raffle, with all proceeds donated to Maine Needs, nonprofit supporting families and individuals with essential items throughout the state. Come shop, mingle, and celebrate the season while supporting local artists and a meaningful cause!
Pizza and Pottery | Friends & Family | 4:00 PM – 9:00 PM
Mark your calendars for an evening of creativity, community, and delicious eats! Join at Friends & Family for Pizza and Pottery, featuring a special holiday pottery sale by Handful Studios and their talented teaching artists. Browse beautiful and functional art perfect for gifts, enjoy mouthwatering pizza and snacks, and sip on wild and wonderful wines by the glass. Plus, there’ll be gift wrapping, jazzy tunes, and a welcoming vibe to make your evening extra special. Come for the art, stay for the fun!
Holiday Blitz! Caravan Artisan Market | Allagash Brewing Co. | 11:00 AM – 4:00 PM (Also Happening Saturday)
Get ready for the ultimate holiday shopping experience! Join Caravan Artist Market at Allagash Brewing’s atmospheric ‘The Cellars’ for this two-day pop-up event. Browse and support over 30 Maine artists and makers, featuring everything from original art and pottery to handmade jewelry, woodworking, skincare, and cozy knitwear. Plus, indulge in food from Black Salt Dining and coffee from Vagabond Coffee while sipping on unique Allagash brews on tap. With a family-friendly vibe and no admission fee, this is your chance to shop local, find one-of-a-kind gifts, and enjoy the holiday cheer!
For more events head to our Events Calendar here.
