The Weekend Guide for May 17th – 19th | Portland Old Port

The Weekend Guide for May 17th – 19th

Ah yes, the weekend before Memorial Day weekend in Portland, time to prepare for the beginning of summer (well not the solstice, but Memorial Day really marks the beginning of summer, right?). Get your boat out, shave your toes, pray your favorite character survives the GoT finale on Sunday. Regardless of what the weather gods, and GoT writers, decide to bring this weekend, we’ve got some great events lined up for you!


Do you like Urban Outfitters? How about helping the homeless? What about getting 10% off your purchase at Urban Outfitters for helping the homeless?! Today through 19th, bring two or more cans to UO in the Old Port to donate to Preble Street and you will indeed get 10% off your purchase.

Happy Fruited Friday! Oxbow Brewing will be releasing three new fruited beers that you don’t want to miss. This all-day event starts at noon!

Calling all Lords, Ladies, Wildings and Sell Swords… Arcadia presents a night of GoT inspired food and drinks as we prepare for the final episode. Starts at 5 pm!

Comedy at a secret pop up venue located in the heart of the Old Port?! We’re in. If you purchase a ticket, you’ll be notified the day of the show of the actual location. This show we feature a New England comedy legend. The show begins at 7 pm!


Definitive Brewing turns one! To celebrate an incredible first year, they’re throwing one big party. There will be three new bears on draught and in cans and will be debuting their brand-new back patio bar. The fun begins at 10 am and goes all day!

Do you know what goes best with sausages and beer? Psychedelic Bluegrass! Head to the Thirsty Pig at 7 pm to hear some original folk tunes by Borscht.

Sister’s Deli is celebrating their three-year anniversary! There will be sandwiches, free Sister’s swag, a corn hole competition and great company from 11 – 3 pm.

Scavenge Portland has taken the traditional scavenger hunt, flipped it on its head, and added in a mini pub crawl. You’ll be asked to find items, take pictures/videos, and explore the best of Portland. Head to Three Dollar Dewey’s at 3 pm or 7 pm on Saturday to get started!


The Southern Maine Heart Walk is the American Heart Association in Maine’s largest fundraising event! Join over 3,000 local supporters for a morning kick-off followed by a walk or timed 5k run around Portland’s Back Cove. Starts at 8:30 am!

Learn to make dandelion wine with Rewild Maine! Meet at Root Wild at 11 am to stroll up to the park to gather dandelions and then return to the kombuchery for the brewing. Everyone will get a bottle to take home after the fermentation process is complete.

If you didn’t get enough of Definitive Brewing on Saturday head right on back from 12 to 5 pm to eat some good food and possibly find your new best friend! The Pixel Fund will be there with some of the cutest pets in the area, all available and waiting for their forever homes.

Put your Game of Thrones knowledge to the trivia test! Head to Fork Food lab from 4 – 6 pm for your chance to win a viewing basket with sweet and savory treats. Tickets include one Fire and one Ice cocktail, snacks, and trivia entry.

Nothing better than some good laughs to prepare you for the week ahead! Empire presents Anders Nielsen headlining Sunday Night Comedy. Starts at 8 pm. This event is 21+.