The Weekend Guide for October 5th – 7th | Portland Old Port

The Weekend Guide for October 5th – 7th

We’re feeling the Fall vibes on this fine First Friday and they’re not stopping all weekend long.


It’s the first Friday of October, so that means it’s time for the First Friday Art Walk featuring shows, programs, food, and drinks at dozens of venues throughout the city! It all starts at 5 pm.

There are just a few spaces left aboard the Fall Foliage Sunset Wine Sail with Wine Wise Events, this time exclusively featuring Emerging European wines, while you enjoy learning all about them and a side of delicious cheeses, fruit, and nuts.  

Keep the art-rich Friday night going with Portland’s premiere of a 5x Tony Award-winning play, The Curious Incident of the Dog in the Night-Time, presented at Good Theater, starting at 7 pm!

Empire’s First Friday Comedy series will feature Dennis Fogg, Steve Cloutier, and Leonard Kimble, with host Ian Stuart! The show begins at 8:30.


If it’s tacos, tamales, pupusas, carne asada, rellenitos, etc. you’re after, the Latino Festival is the place for you, starting at 12 pm! All proceeds will benefit the Sacred Heart Church!

Songs, Spirits, and Swashbuckling with the Portland Rugby Football Club… Sounds like a great time to us! Join them for a Pirate Pub Crawl starting at 2 pm at Gritty McDuff’s with rum specials there, Foreplay, and Oasis, a 50/50 raffle, pirate costume contest, and cash prizes.

The Noonday Crawlers are bringing their funk/blues/rock with a side of spook sound to the Thirsty Pig starting at 8 pm and it sounds like just the thing to get you in a spooky October mood.

If UFC is your thing, don’t miss the UFC 229: Khabib vs McGregor viewing party at Fore Play! And for those who want to get their dance on, DJ El Shupacabra will be playing upstairs. Just a $5 cover at the door!


If your Saturday was rough, Bull Feeney’s wants to help you out. Get in early and take 15% off your entire Sunday Brunch tab, starting at 10 am!

If you find yourself in Deering Oaks Park from 11am-5 pm you’ll be surrounded by food, live music, activities for the whole family, giveaways, raffles, artists, craftsmen, and more for the Portland Harvest Festival! This celebration of Fall will be raising funds to increase literacy within Portland Public Schools.

The Second Annual Oyster Festival will commence at Ri Ra, sponsored by Guinness benefit Full Plates Full Potential! Enjoy live music, an oyster shucking competition with chefs from Maine’s finest restaurants, an oyster bar, locally sourced seafood specials, live auction, raffle prizes, and more! This event is free and all ages friendly and begins at 11 am!