Like Santa Claus on Christmas Eve, December has come to town and it’s sure showing across the city. Simply put, the holiday season in Portland is on as the city kicks off the first weekend of December with a slew of festive celebrations including SantaCon (they’re coming in droves and crawling to a bar near you!), Holiday markets and pop-ups (there are many!), Red & White Anniversary Party (beers, lobster and cocktail insanity!), and Holidays at Hadlock (Slugger and Santa sightings in store!)
Here’s the Weekend Guide for Friday, December 2nd – Sunday, December 4th, 2022
Friday the 2nd
A Tuna Christmas | Portland Stage Co. | 7:30 PM (Multiple Dates + Times)
Are you ready for a funny holiday show? The Tuna Plays are fierce and funny satires of life in Texas and all around this country. Like an American Chekhov– this play features flawed, sometimes truly horrible, funny human beings doing the best that they can and not succeeding. Portland Stage Co. delights in poking fun at the powerful and uncomfortable forces in our lives. A Tuna Christmas lives in this long tradition, and PSC encourages you to join them for to laugh, think, and contemplate. Tickets here.
Holiday Pop-Up Shop | Indigo Arts Alliance | 12:00 PM – 8:00 PM (All Weekend)
Stop by Indigo Arts Alliance for an opportunity to take home exquisite works of art from their past Artists-In-Residence and some of the incredible Black and Brown artists in the global community! On First Friday they will be hosting a Freestyle Friday Live with their friends from Signature Soul. On Saturday, December 3rd from 10pm – 1am they will throwing an after party at The Jewel Box with DJ Ben Spalding, their current David C. Driskell Fellow. (A suggested cover of $5 as all proceeds will go to supporting Indigo Art Alliance and their mission of Art + Activism in 2023). Last but not least on Sunday, December 4th from 2-4pm Kafari will be in the studio creating an ethereal Sunday Soundscape to close out the final day of the shop!
Holiday Art Fair | Ruby’s West End | 5:00 PM – 8:00 PM
Join Ruby’s West End For December’s First Friday Art Fair with original artwork from friends around Portland. Local artists showcase their work and offer interactive creations from 5 pm – 8 pm. Fill your gift list with original artwork from Portland based artists Kbuurns, Dylan Quinn, Robin Carlson, Art By Lil, and your host “Dont Look at This Dave”! $5 Glass Pour Wine + $2 PBRs!
Toby McAllister | Aprés | 7:30 PM – 9:30 PM (Repeats Sunday)
Live music at Aprés! Toby McAllister has been playing music since he got his first guitar when he was 13 years old. He immediately realized this was his passion, and hasn’t stopped playing/performing since. Out of high school, Toby formed Sparks The Rescue, which went on to tour the world. Notably, Sparks did the Van’s Warped Tour in 2010, toured Europe/UK with The All American Rejects, and have had their music on MTV. After the touring slowed, and the band members started settling down, Toby found his place back in his home state of Maine where he continued playing music as a full time job.
NAWA Wrestling | Geno’s Rock Club | 8:30 PM – 11:30 PM
Live Pro Wrestling returns to Geno’s Rock Club with a great night of action. Local band “Alions” plays at 8:30pm and the wrestling starts at 9pm sharp. Wrestlers scheduled to wrestle will include: NEW North Atlantic Champion “Big” Geno Bauer, Cousin Larry, Flash Nick McKenna, and more. 21+ event. $10 cover at the door.
Saturday the 3rd
Santacon | Old Port | 5:00 PM – 12:00 AM
Join hundreds of other Santas on an epic bar crawl! Make some friends. Have a few drinks. It’s been a while, so everyone is a little rusty… and, the best way to clean off that rust is alcohol. A full Santa suit is the classic (If you’re in just a hat, you’ll feel underdressed), but the group is open to others if they’re creative (Reindeer, Christmas trees, leg lamps, a few snowmen, actual-lit-up trees, and even Hanukkah Harry.) Group photo around the Monument Square tree around 7pm. 21+ event. Map of participating locations here. There are no tickets – The full costume is your ticket for entry.
Speckled Ax Mugstock 2022 | Speckled Ax – Thames Street | 7:00 AM – 2:00 PM
1 day of mugs and coffee! Speckled Ax invites local potters, ceramic artists and shoppers to their Thames Street shop for a day of showing off handmade mugs and drinking vessels, and the general public for a day of purchasing them! There’s no cost involved—they just like the idea of a room filled with cool mugs, and giving artists a place to make some money during the holidays.
Holiday with Santa & Gingerbread Houses | Woodfords Club | 10:00 AM – 1:00 PM
For children of all ages! Get in the holiday spirit with photos with Santa, gingerbread houses and hot chocolate! Pictures with Santa, whether with individuals or groups, will help you keep memories alive. Decorating your own Gingerbread House will showcase your artistic skills and can become a centerpiece for your table for the holidays. Finally, at the Hot Chocolate Bar, you can add several delicious toppings such as peppermint sticks and whipped cream to your hot chocolate. Profits from this event benefit Woodfords Club’s restoration and preservation efforts. $10 for each photo and $10 for each gingerbread house. Part of Woodfords Weekend.
LIVE Music with James Humphrey | Dogfish Bar & Grille | 7:00 PM – 9:00 PM
Do you miss hanging out at Dogfish during their closure? Does you miss Travis James Humphrey ? Do you miss Travis playing at Dogfish? Yeah, well The Dogfish Bar & Grille feels the same way. For one night only they are going to unlock the doors for a night to bring him back! There will be drink specials galore, great company and music. It’s the holiday season and there is no better way to celebrate. $15 cover charge at door.
Red & White Anniversary Event | Highroller Lobster Co. | 7:00 PM
Highroller Lobster Co. is honored and excited to bring back their signature anniversary event, the Red & White Party, to ring in five wonderful years of lobster, beer, and cocktail insanity. To mark five years of wild ups and downs they have blown out all the stops and are excited to debut a full tap list of collaborations with some of their closest colleagues in the beverage industry – a wide variety of beers, ciders and seltzers that you’re gonna love. A photographer will be on hand to capture you in your finest red and white attire on the red carpet, and upon entering you’ll be met by plenty more surprises and delights. The kitchen is closing at 7pm so the whole staff can take part in the festivities. Guest bartenders will be taking over for the same reason. No cover.
Sunday the 4th
Move Wild: Brewery Yoga | Oxbow Brewing Company | 11:00 AM – 12:00 PM
Move Wild Studio is excited to be collaborating with Oxbow Brewing Company for a special event: Yoga Flow – an all levels 50 min Vinyasa YOGA Class. Get ready to feel centered and grounded as you connect breath with movement. Flow together then hang out with a delicious Oxbow Brew for a Cozy Sunday Funday. Tickets here.
Barre & Brew | Urban Farm Fermentory | 10:00 AM – 11:00 AM
Join Pure Barre Portland for this FREE Pure Barre Pop-Up class! Attendees will be led through a 45-minute Pure Barre class followed by complimentary pours of UFF Jun or Kombucha and additional sweet surprises. Attendees are welcome to stay and enjoy a special Winter Market event post-class. This class is FREE and open to the public. Space is limited. Reserve your spot online at Pure Barre Portland.
Holiday at Hadlock | Hadlock Field | 10:00 AM – 12:30 PM
After a two-year absence due to Covid, the Sea Dogs will host Holiday at Hadlock where they will turn the place of summer memories into a winter wonderland, highlighted by Santa’s arrival from the North Pole via helicopter (ELF One). Santa Claus is scheduled to land at 11:00 AM at Hadlock Field from the North Pole. Festivities also include an arts and crafts room, free hot chocolate and cookies, make your own s’mores station, holiday music, Toys-for-Tots drop-off location (fans are encouraged to bring a new unwrapped toy to donate), face painting, photo ops, Slugger the Sea Dog and more. Free event.
Christmas Tree Sale | Chaval | 10:00 AM – 2:00 PM (Happening Saturday Too)
Get Your Christmas Tree For A Good Cause – Chaval is partnering with Barbara Bush Children’s Hospital at Maine Medical Center for their Christmas Tree Sale! Chaval will have local Maine Christmas trees for sale from Allagash View Farms and all proceeds from the sales will benefit The Barbara Bush Children’s Hospital. They will also have some local Artisans selling beautiful items for your holiday gift giving. On Saturday they will have coffee and baked goods from Chef/Owner Ilma Lopez and on Sunday they will be open for a Chaval “Pub” Lunch (awesome!)
For more events, head to our full Events Calendar here.