The Weekend Guide for Dec 7th – Dec 9th | Portland Old Port

The Weekend Guide for Dec 7th – Dec 9th

Lots of delicious beers, great food, prime holiday shopping, beautiful faces, and ugly sweaters. That’s what this weekend in the Old Port is made of.


Join Flight Deck Brewing at Maine Oyster Company for an incredible night of sipping and slurping. Sample a fantastic selection of their beers and enjoy a wonderful selection of local oysters starting at 4 pm.

If there’s ever been a time to find yourself at the First Friday Art Walk, it’s this one! Make your list and check it twice as you stroll through various downtown Portland establishments and find gifts for that special someone you’ve got.

Escape the holiday madness and join Fork Food Lab for the ultimate treat-yo-self happy hour. Unwind with a glass of Cellardoor wine, snack on your own mini cheeseboard with local cheese and crackers, get a 10-minute restorative chair massage, and shop a selection of beautiful silver & turquoise jewelry by local company Lazuli Maine. It starts at 5 pm, and a % of all proceeds go to Full Plates Full Potential!

Also starting at 5 pm, MECA’s Holiday Sale supports education, outreach, and student programs while providing an opportunity for you to purchase unique, one of a kind gifts for the holiday season.


Get your hands on some LiveME merch while you sip on fresh beers at Rising Tide Brewing Company. Shop gifts for your favorite Mainer or Maine lover starting at noon!

No one does a Classy Christmas party better than Michael Scott, but Oxbow Brewing is giving it a shot starting at noon! There’ll be holiday beers, eggnog, a tree lighting, tons of Christmas music, and oysters from the Shuck Shack… OH and a live string quartet.

The 2nd Annual Ugly Sweater Bar Crawl is here! Get the ugliest and most festive holiday sweater you can find and head to 10 participating Old Port bars to enjoy their specials while enjoying tons of amazing specials at each one, starting at 5 pm!

Take a musical break from holiday hullabaloo with Dan & Darren as they play at The Porthole while you enjoy fresh seafood & yummy drinks!


Bust out the ugliest of your holiday sweaters, Santa suits, festive tops, and leggings for Be Well Bend & Brews: Ugly Sweater Edition! Get your workout in with a 1 hour of power featuring half body weight sculpting and half vinyasa flow, followed by a beer and a protein bar to refuel. It starts at 10:30 at Oxbow Brewing!

Join Margaritas from open to close for a Sunday Funday Football Fiesta including specials like $4 drafts, $6 house margaritas, and ½ price select apps.

Boston Music Awards’ “New Artist of the Year” nominees, Gentle Temper will return to Bissell Brothers to perform while you enjoy their beer and maybe even a few bites from the Locally Sauced window.