A holiday weekend filled with national touring acts, an aerial acrobatics show and an outdoor flannel party that can’t be missed!
Friday, October 8th
Fall Foliage Wine Sail | 4:00 PM – 6:00 PM | Maine State Pier | Tickets
You’re in for an incredible wine education experience as you sail through beautiful Casco Bay, in Maine’s most colorful season, with scenic views of Maine lighthouses, islands, and waterways, and fall foliage colors in the backdrop … all while indulging in a wine class.
CAKEWALK: Lou DiFunk | 9:00 PM – 1:00 AM | Citrus
DJ Lou’s love of all things electronic music brought him to the level of wanting to learn how to DJ. He has lived in various countries, including Indonesia, Italy, and Sweden before finally residing in Boston, MA. These places had a profound effect on Lou’s love of music, dancing, and understanding on how music plays a role globally for people both politically and personally.
Scenes of Maine: Annual Exhibition of Paintings | 10:00 AM – 5:00 PM | Richard Boyd Art Gallery
This year’s exhibit is another great show of paintings documenting scenes in Maine through the eyes of artists with diverse backgrounds, perspectives, and styles.
Dimensions In Jazz: Rj Miller | 8:00 PM – 9:30 PM | Portland Conservatory of Music | Tickets
Electronic music comes in all sounds, colors, and textures, but drummer RJ Miller exploits the ambient side with chilled themes and moody soundscapes. The soul in the machine lies in the way Miller expertly juxtaposes his drum kit with piano, keyboards, and analog synthesizers through infectious melodies that move and groove.
Saturday, October 9th
Martina McBride | 8:00 PM – Close | Merrill Auditorium | Tickets
Contemporary country singer Martina McBride rose to stardom in the late ’90s, and early 2000’s starting with a more traditionalist approach in country music and later moving into more pop-friendly territory.
Latin Logic Salsa Band | 9:00 PM – 1:00 AM | The Yard | Tickets
This unique group aims to respect and maintain the tradition of old school salsa with a special touch of Latin jazz and Afro Caribbean rhythms, making it a fusion of flavors throughout Latin America.
Queer Makers Market | 11:00 AM – 3:00 PM | Congress Square Park
Come one, come all to a one-day market event featuring all queer artists, makers, doers, and shakers.
BANDALOOP| 1:30 PM – 4:30 PM | Canopy | Free Event
This unique act re-imagines dance, activating public spaces and inspiring wonder and imagination in audiences around the globe. An innovator in vertical performance, BANDALOOP seamlessly weaves dynamic physicality, intricate choreography and climbing technology to turn the dance floor on its side – literally.
Bikes & Beers | 7:00 AM – 2:00 PM | Definitive Brewing | Tickets
2nd annual event! Bikes & Beers Portland features a 15, 30, and 45-Mile ride departing from Definitive Brewing Company and traveling through the beautiful area of Portland, ME. All rides feature morning fuel stations, marked routes, GPS turn-by-turn instruction, rest stops, refreshments, ride marshals, and SAG support. Finish back at Definitive for a festival atmosphere of rewarding craft beers, live music, charity raffle & much more! All riding levels are welcome!
Filipino Street Food Pop up | 11:00 AM – 3:00 PM | Woodfords Corner
Round two in this food contest to see who has the best Filipino food! As always, get a taste of popular Philippines’ Street Foods in one pop-up event! Weekend Merienda in partnership with Veterans of Foreign Wars, Portland ME. Come and celebrate food in a whole new way!
Sunday: October 10th
Blue October | 7:00 PM – 1:00 AM | Aura | Tickets
Blue October is an American alternative rock band originally from Houston, Texas. The band was formed in 1995. The band has had sixteen Top 40 singles over their past eight studio albums and is best known for their platinum singles “Hate Me” and “Into the Ocean”
Flannel Jam | 2:00 PM – 8:00 PM | Maine Craft Distilling | Tickets
Hoot and Holla! Flannel jam is Levitate’s touring celebration of fall in New England. Featuring peak fall foliage, hot cider donuts, hot cider & whiskey, caramel apples, a kid’s corn pool/hay maze and so much more.
Rising Vibes Live Music | 1:00 PM – 4:00 PM | Rising Tide Brewing
Rising Tide Brewing Company is an independent, family-owned brewery that anchors Portland, Maine’s vibrant East Bayside neighborhood. Shoot on down and enjoy live, music all afternoon
Global Mental Health Awareness Day | 10:00 AM – 11:00 AM | Monument Square
October 10th is Global Mental Health Awareness Day. Join us to smash the stigma, spread hope and plant a yellow tulip bulb
SPOUSE with Dominic Lavoie & Tiger Saw | 7:00 PM – Close | Sun Tiki Studios | Tickets
SPOUSE is a band led by lead singer and guitarist José Ayerve and drummer J.J. O’Connell. The band formed in 1995 and has seen a revolving line-up throughout their decades-long career. The band—currently performing as a trio with co-writer and bassist Marc Seedorf—has been completing work on a long-awaited rock album, Feel Good Everywhere
Monday, October 11th (Indigenous People's Day)
Postmodern Jukebox | 8:00 PM – 11:00 PM | State Theatre | Tickets
Join the most original cover band for the best 20’s party this side of the Great Gatsby. So much energy and talent on one stage will make YOU feel 20 again
Indigenous Peoples’ Day Dinner | 6:00 PM | Lukes Lobster | Tickets
Lukes Lobster will be honoring Indigenous Peoples’ Day with a five course fundraising dinner on October 11, from 6-9 pm. All profits from ticket sales will go to Wabanaki REACH, an organization led by the Wabanaki people that supports the self-determination of Wabanaki people through education, truth-telling, restorative justice, and restorative practices in Wabanaki and Maine communities.
More event listings within Portland, Maine: CLICK HERE