The Weekend Guide for October 4th-6th | Portland Old Port

The Weekend Guide for October 4th-6th

It’s getting chilly out there, but Portland, Maine is heating up! Snag a ticket to the Downtown Portland Oktoberfest, attend a fundraiser/cocktail party for breast cancer, or visit the Children’s Odyssey Community Fall Festival!


Grab some goodies at the Pop Up Markets at Rising Tide Brewing Company from 12-7pm. Three to five Fork Food Lab members will set up at the Brewery to sell their delicious local food. Grab ready-to-eat and pre-packaged goods all while drinking a delicious brew!

October’s First Friday Art Walk will be from 5-8pm. Check out all the amazing art and culture Portland has to offer!

Support Planned Parenthood at the More than Ever 2019 fundraising event at Aura from 6-9pm. There will be storytelling, hors d’oeuvres, delicious desserts, and activities!


The Children’s Odyssey Community Fall Festival will be held from 11am-4pm at Children’s Odyssey. Entry is by donation and there will be a ton of fun kids activities including lawn games, a bounce house, face painting, animal visitors, crafts, and more! There will be Fall treats and lunch available for purchase! 

Get ready to jam at Bluegrass Bunker Saturday from 4pm-7pm at Bunker Brewing Company. There will also be Tacos La Poblanita starting at 11am!

Snag a pair of tickets to Downtown Portland’s Oktoberfest Sponsored by Sam Adams. This event runs from 4-10pm. Tickets are $15 for early birds and $20 general admission. They include a T-shirt, refillable pint glass, map, and drink specials at participating bars. There will also be costume contests at some of the bars, so come in your very best get-up! This is a 21+ event. Registration is at Pat’s Pizza.

Attend Witches Wear Pink Breast Cancer Fundraising Cocktail Party at Aura from 7-11pm. This is the 7th annual Breast Cancer fundraising event and supports Maine Cancer Foundation, MMC Breast Care Center and New England Cancer Specialist. Enjoy cocktails and hors d’oeuvres while bidding at the live auction. There will also be live music, so get ready to dance! This is a 21+ event so bring your ID! 


Attend Community Storytime at Print: A Bookstore from 11am-12pm. This event is geared towards ages 2-6 but all are welcome! There will be stories read and activities focused on celebrating the local community.

Get a ticket to the film Miles Davis: Birth of the Cool at the Portland Museum of Art. The movie runs from 2pm-4pm and features never before seen footage, studio outtakes, and rare photographs.  

Tickets for Freshmen Orientation 2019: Meet Maine’s Newest Brewers are on sale! Gather at Bayside Bowl from 3-5pm to meet the people behind Maine’s newest breweries. This event is a fundraiser for the Maine Brewer’s Guild. Tickets include samples, a souvenir tasting glass, and snacks!