Portland’s Old Port Is Celebrating Halloween Early With a Costume-Filled Bar Crawl

Your Halloween Costume Could Win You $100 at This Portland, Maine Bar Crawl

If you’re putting time, money, and possibly a little hot glue into your Halloween costume, you might as well give it more than one night out. Especially when there’s $100 on the line.

Portland’s second annual Boos & Booze Halloween Bar Crawl is happening Saturday, October 24, from 4 to 10 p.m., giving you a reason to celebrate a full week before Halloween.

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And this isn’t a pick-one-bar-and-stay-there situation. The published lineup features nine Old Port stops, turning your night out into a costume-filled trip around downtown.

Your Costume Could Earn Its Keep

The $100 costume contest is what caught my attention. We all have that friend who treats Halloween like a competitive sport, and this feels like their moment.

Tickets also include two complimentary shots, drink specials, an event map and lanyard, and event photography. So yes, there should be evidence of that group costume you somehow convinced everyone to wear.

Where’s Everyone Heading?

Registration takes place at Fore Play Sports Bar. Other participating locations include Glass Lounge, Tomaso’s Pizza & Bar, Three Dollar Deweys, Bonfire Country Bar, Gritty McDuff’s, Rosie’s Pub, and Andy’s Old Port Pub. The Porthole is listed as the official after-party location.

Honestly, a parade of Halloween costumes making its way through the Old Port sounds like people-watching gold.

Grab your friends, settle the costume debate, and check the official event page for tickets and updated details. Just get your ride home planned before the festivities begin.