The Weekend Guide for September 14th – 16th | Portland Old Port

The Weekend Guide for September 14th – 16th

In a desperate attempt to squeeze the last few bits of summer out of this beautiful mid-September weather, we present to you, The Weekend Guide.


Now that it’s mid-September our rooftop days are numbered. Join Foundation Brewing Company for a party on the Bayside Bowl rooftop with music, tacos, and great times starting promptly after work at 5 pm. Is this what they call kismet?

Catch the bourbon-flavored cajun mayhem of Sylvain’s Acadian Aces at Maine Craft Distilling starting at 7 pm! There’ll be dancing, cocktails flowing, and an all-out cajun style romp.

Party the night away with Portland’s kicking, flipping, and splitting drag queen Kat Walker for Drag It Up Empire. She’ll be lip-syncing the house down and shock you into laughter with her sassy stand-up comedy with special performances by Cherry Lemonade, Gigi Gabor, Paxil, Lady Ginger, and Mizz Diveena starting at 9:30 pm at Empire Live Music & Events.

We’re pretty sure the only connotations we have with Fridays are good ones, but el malo begs to differ. They’re bringing you a Bad Friday with good music starting at 10 pm at Blue!


Do your good deed of the day and join Casco Bay Cleanup Project for their Low Tide Tidy: Coastal Cleanup at 9 am on East End Beach to clear the beaches of debris and garbage, enjoy free Bard coffee, and ocean-friendly giveaways!

We didn’t think there could be anything better than Oktoberfest, until Bunktoberfest came along. A crisp $20 bill will get you a Bunktoberfest stein, .5L of beer, music, and access to the traditional Bunktoberfest Bouncy Castle! It starts at Bunker Brewing at noon with food by Terlingua, music by Raging Brass, and Ice Cream from The Parlor Ice Cream Co.!

Catch the Portland Rugby Football Club take on the Boston Irish Wolfhounds RFC, a fall league fixture at the Fox Street Field starting at 1 pm!

Hop aboard Casablanca’s final booze cruise of Summer 2018! This Great Gatsby themed party is a chance for you to look snazzy and dance the night away on the beautiful Casco Bay! Put together your swankiest roaring 20s themed party getup and get on board at 6:30 pm.


Join the Portland Flea-For-All for Flea Bites in Congress Square Park for a new lineup of trucks, carts, and special menus, complemented by Portland’s favorite vintage, handmade, and antique dealers starting at 11 am!

Fall is here but the beer is still fresh at Rising Tide Brewing Company! Head to their patio to enjoy a cold on and local music by Bread & Circus starting at 1 pm.

The long, long winter is looming over our heads, let’s get as much time with live music on the Porthole deck as we can, this time with Country Roads starting at 2 pm!