A beautiful, crisp Fall weekend is here, and we have more then enough events for you to fill your entire weekend with fun! This is your weekend guide.
Friday, October 22nd
BLOCKHEAD w/ Arms & Sleepers | 8:00 PM – 11:30 | Bayside Bowl | Tickets
Blockhead returns with his first tour since the start of the pandemic, showcasing music from his upcoming new album ‘Space Werewolves Will Be The End Of Us All’. He is regarded as one of the modern masters of instrumental hip-hop and has more recently been releasing music on other platforms like Future Archive Recordings and Backwoodz Studios.
The Marc Chillemi Quintet | 10:00 PM – Close | Blue
Marc Chillemi is a Portland-based musician and composer active in Jazz and roots music from the Caribbean and West Africa. For 30 years Marc has amassed a considerable list of performances and recordings across a wide range of styles and genres.
Love w/ Keenan Orr | 8:00 PM – 1:00 AM | Flask Lounge
Keenan Orr has been a mainstay in Washington DC’s underground dance parties and clubs since the ’90s, including Buzz (DC) at Nation, Red, and Club Five.
Mouse on the Move | 4:00 PM – 5:00 PM | Children’s Museum & Theatre of Maine
Is the moon made of cheese? Two curious and hungry mice will attempt to find out in this magical and whimsical story. Help the mousey pair make new friends and explore the world outside their mouse hole. Ideal for children ages 0-5 and their families. Tickets are $15 per person for adults and children. Each child ticket includes an interactive storytelling travel bag for young audiences to use during the play and take home.
Walk Among the Shadows | 6:30 PM | Eastern Cemetery | Tickets
Ghostly storytellers, some buried at Eastern Cemetery, will materialize in the cemetery to tell their own stories. The stories were written by Lynne Cullen who also directed the spirits (as best she could—you know spirits, sometimes they listen, sometimes they don’t.)
Habibi w/ Dead Gowns | 7:30 – Close | SPACE
As the world starts to re-emerge and awaken, Habibi is ready to dance. After being coined by the New Yorker as having the Colgate white glisten of sixties girl group pop combined with an uncensored edge, for their acclaimed debut album, Habibi broke boundaries by introducing Farsi-sung tunes on their EP ‘Cardamom Garden’ that “shed rigid definitions of what constitutes American music.
Retro Fridays | 9:00 PM – 1:00 AM | Aura | Tickets
Internationally renowned DJ’s Innox and Jimmy Tabz along with the guest Djs and event planning expertise of AURA bring you retro nights. Come celebrate different music vibes with us, and different genre of music with the best Djs around.
Saturday, October 23rd
Fall Pop-Up Sale | 10:00 AM | 160 Presumpscot Street
Put on a sweater for the Kendrick & Bloom Fall Pop-Up Sale! Join everyone for some outdoor fun: Pumpkins for sale, with pumpkin carving stations, Live music, Homegrown teas and local treats, Local artists selling their art, and more! Pull up a hay bale to meet some old friends and make some new ones while you get a pumpkin, some fresh brew and support local artists. See below for some of our participating artists & vendors. Indoor/outdoor event.
Jay Larkin | 8:30 PM – Close | The Yard
Jay Larkin is a local solo acoustic musician. Having played solo and in the band Skosh for many years. He has shared the stage with acts such as The Charlie Daniels Band, The Marshall Tucker Band, and Randy Houser. Utilizing a loop station, He plays covers of all genres ranging from Old school funk/soul, 90’s Alternative, and reggae to rock, country, and blues.
Children’s Odyssey Community Fall Festival | 11:00 AM – 3:00 PM | Childrens Odyssey Preschool
Let the gourd times roll! This event has a multitude of things for you and the kids to do including: Food and drinks, Games and activities, DJ music and dancing, Animal visitors, Firetruck and police car visits, 2 magic shows, and more! All are welcome for this outdoor celebration!
Ryssa & Nic Optimistic | 9:00 PM – 1:00 AM | Citrus | Facebook Event
- Ryssa spins anything from deep house to techno sprinkled with remixes. She creates the vibe so you can lose yourself on the dance floor.
- Nic Optimistic is not one to shy away from an engaging performance while mixing tracks. His selection of songs is driven by the energy and connection he strives to share with those who came to dance. He keeps the dance floor moving with a collection of various house music genres centered on catchy vocal hooks and bass lines.
Portland Elks Fall Harvest Craft & Bake Sale | 9:00 AM – 4:00 PM | Elks Club, Congress St.
Craft Fair featuring 25+ vendors from all over Maine – soaps, candles, jewelry, Christmas wreaths, painted glass, tumblers, wooden pallet signs, knit goods, and so much more! Italian Pastry & Candy Sale; 50/50 Raffle; lunch served 11:00 am – 2:00 pm. Free admission. Plenty of Parking!
Wake Up Mama | 7:00 PM – Close | Sun Tiki Studios | Tickets
A Tribute to the Allman Brothers Band. A benefit for the preble street’s homeless support services. The band will keep you on your feet all night long, this event is a must if you like fun times, great drinks, and even better vibes.
Sunday, October 24th
Dopapod | 8:00 PM | Aura | Tickets | Facebook Event
Symmetry defines Dopapod. The band and each of its seven albums sports a palindromic name, meaning it can be read the same forward as backward. More than that, balance has become the band’s modus operandi, with the group consciously juggling the darker tones of heavy rock with lighthearted humor; synthesizing tastes of funk, jazz, bluegrass, electronica, and more within their complex improvisational compositions. During live shows, Dopapod is known for taking fans on a full-out journey, guiding attendees through periods of frenzied dance contrasted with moments of thoughtful contemplation.
Build Your Own Board with Chartcutemarie | 1:00 PM – 2:30 PM | Three of Strong Spirits | Tickets | Facebook Event
Come join Charcutemarie & Three of Strong Spirits for an afternoon of yummy food & delicious craft cocktails! Each ticket includes:
- One Complimentary Cocktail
- Artisan cheeses, cured charcuterie and all additional accompaniments (honey, fruit, nuts, etc.) for creating the perfect board on a disposable palm leaf tray.
- Step-by-Step guidance in creating a charcuterie board with pairing and styling tips led by Marie of Charcutemarie
- Honey dipper
- Small personalized gift
PugOween Party | 12:30 PM – 2:30 PM | 24 Whitehead Cir, Pocrtland, ME
You heard that right, PugOween Party! A group of pug owners in Portland, Maine and surrounding communities that like to get together and hang out with their dogs. Join them for some Halloween fun! Lots of pugs having fun. Prizes for the best Halloween costume!
All Hallows’ Market | 11:00 AM – 3:00 PM | Congress Square Park
Get ready for Halloween with Congress Square Park’s first-ever All Hallows’ Market! Enjoy Halloween-specific crafts, cards, art, accessories, and more, as well as hot cider and apples for purchase from Sweetsers Farm! Plus, you can get your face painted!
Cars & Coffee | 9:00 AM – 11:00 | 245 Western Ave, South Portland, ME
If it has wheels and you love it, we love it! This is a free event for any auto enthusiasts (vintage, new, import, euro, classics, domestic) please join us to hang with like minded people, and help raise money for Midcoast Humane with our 50/50 raffle!
Pumpkin Decorating and Apple Cider Mimosas | 11:00 AM – 1:00 PM | 42 Resurgam Pl, Portland, ME
Rosemont Bakery’s newest location on Thompson’s Point, Rosemont Market & Wine Bar, is hosting a Sunday Funday: Fall Edition. Fun for all ages, there will be pumpkin decorating, apple cider mimosas, hard cider tastings, and more! Their lawn space will be open for those who wish to gather outdoors.
For more of what’s happening in Portland, visit our Events Calendar HERE.
