The Weekend Guide for September 21st – 23rd | Portland Old Port

The Weekend Guide for September 21st – 23rd

The weather might be getting a little chillier but that won’t stop us from getting out to enjoy a weekend full of fun in the Old Port!


Support your local fire department and local breweries at the 2nd Annual Boots, Brews, and Bites with Nonesuch River Brewing Company! Enjoy brews from local breweries, paired with bites from local restaurants, while supporting local firefighters! The fun starts at 4 pm.

Waking Windows is back! Two days full of local talent including 100+ bands, authors, artists, DJs, comedians, and thinkers across 18 venues throughout Bayside and Congress Street!

There are just a few highly coveted tickets left for the Fall Foliage Sunset Wine Sail, featuring sparkling wines with Wine Wise Events! Enjoy a beautiful sail aboard the 74-foot sailboat, Frances while you sip on and learn about delicious wines and enjoy a selection of cheeses, fruit, and nuts.

Third Friday means Danny & Jake are bringing their guitar and cello to Bull Feeney’s and playing indie covers from 9:30 pm!


We’re so happy we live in a world where there are Oktoberfests. Slab is holding their annual Oktoberfest with themed pizza specials, 15 different Oktoberfest beers, and music on the patio! Beer and food starts at 11, music starts at 5 pm.

Join Orono Brewing Company on the Bayside Bowl rooftop from 4-7 pm with a couple hundred OBC cans, including their Fruitful Kettle Sour and 44 North Coffee Stout! No cover charge, and as always, tacos… Need we say more?

Kick off the first day of fall by cruising the Casco Bay with the Red Shoe Society to benefit the Ronald McDonald House of Maine! Complimentary food and a cash bar for a good cause… Sign us up. It sails at 6:30 pm!

Maine’s favorite bluegrass band, The Moosetones are coming to the Thirsty Pig! You know what else will be there? Really good food and really good beer. The music starts at 7 pm!


The second annual Dirty Gears and Local Beers bike ride will commence at 10:30 am at Coffee By Design on Diamond Street. It starts with a mandatory espresso, followed by the first beer stop at Allagash!

Royal Hammer will be bringing the reggae vibes to Bunk Brewing Company for one last summer live music session! No Wolfpack will be DJing between sets, Kind & Company will have a pop-up shop, and Thainy Body will be serving up food 2 pm to sell out!

Join the Honor Movement Studio in the woods for a donation based, outdoor yoga session from 3-4 pm! BYO Mat and good vibes.