Bella's Bingo Ball
Hosted by the Berkshires’ favorite BINGO queen, Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes, fierce vibes, and a little extra witchy wonder! October’s bingo features The Burrow as our special partner, supplying thr prizes and bringing fall favorites to shop throughout the evening. Come for the bingo, stay for the spells and shenanigans!
Rocky Horror Pre-Show Party at WANDER Berkshires
Get ready to do the Time Warp! Join us at WANDER Berkshires starting at 6 PM for a fabulous pre-show party celebrating The Rocky Horror Picture Show. Come dressed to impress, embrace the outrageous, and soak up the gothic glamour before heading to the Boyd-Quinson Theatre for the screening.
Whether you’re a longtime Rocky Horror fan or a first-time “virgin,” come kick off the night with music, costumes, and plenty of decadent, delightfully strange energy.
Costumes and fabulous attire are encouraged! Costumes must be audience-friendly: no nudity, no full-face masks, and nothing that blocks the view of those seated behind you.
WANDER Halloween Karaoke + Dance Party
HALLOWEEN AT WANDER
THURSDAY, OCTOBER 29 · 8–11 PM
$10 COVER or PWYC
It’s astounding. Time is fleeting. Madness takes its toll.
Join us at WANDER for a Halloween celebration inspired by the one and only Tim Curry and the cult classic that made him a legend: The Rocky Horror Picture Show.
We’re kicking off the night with ROCKY HORROR KARAOKE from 8–9 PM with Casi & Ash — grab the mic, choose your favorite character, and give us your best rendition of your favorite RHPS moments.
DJ Harsh Noise Boyfriend takes over from 9–11 PM with leftfield dance, bootleg edits, global club sounds, and experimental noise built for the WANDER dance floor.
No WANDER Halloween party would be complete without the infamous Luna Fire Faun will be bringing the heat with a live performance.
Come dressed as your favorite Rocky Horror character, your favorite Tim Curry incarnation, or simply come as you are. Costumes encouraged for a costume contest with prizes. Everyone welcome.
PRE-PARTY WITH BARRINGTON STAGE
Before the party, join us for a special Rocky Horror pre-party with Barrington Stage, celebrating this legendary cult classic and getting everyone ready to let loose at WANDER.
Karaoke · Dancing · Drag · Fire · Rocky Horror · Tim Curry
One night. One very big Time Warp.
Only at WANDER.
Supportive Community Gathering
Parents, families, and caregivers of trans*, non-binary, and gender expansive young people are welcome for this peer-driven social support group. Facilitated by Kelly Heck, LICSW, there will be a focus on sharing lived experiences as caregivers, and opportunities to discuss the joys and challenges of supporting our young people in their journeys.
Community Potluck
Rainbow Seniors & Stonewall Monthly Potluck
Join Rainbow Seniors and Stonewall for a monthly community potluck at WANDER, held on the first Thursday of each month from 4–6 PM. This welcoming gathering is a space for LGBTQ+ adults and allies to connect, share a meal, and build meaningful community in a relaxed and inclusive environment.
Bring a dish to share (if you’re able), enjoy good conversation, and spend time in a space rooted in care, creativity, and belonging.
Free. All are welcome.
Narrative Processing + Liberatory Visioning Workshop
Join us for our monthly Narrative Processing + Liberatory Visioning Workshop
This is a casual, communal gathering hosted by seeing rainbows, where we hold space with writing, reflection, and collective dreaming. Together, we stand intentionally in the liminal space between past and present, drawing on the generative energy of the group and the container we build to nurture a shared sense of liberation.
In this continuing workshop (2nd Sunday of the month), we’ll explore the power of narrative for visioning and healing; though rooted in writing, all mediums and forms of expression are welcome.
This is an open workshop, with cis allies welcomed. Come early to grab a beverage and snack.
Protest Open Mic
Protest Open Mic with host Robin OHerin
Every Second Wednesday of the Month
Bring Poems, Spoken Word, Songs and more….
FREE AND OPEN TO ALL PEOPLE ALL AGES
COME ONE - COME ALL!!!
Brick & Sip
We’re teaming up once again with Bottomless Bricks to offer an adults-only evening of building. Each month will be a themed build and your ticket also includes a zero-proof beverage from Wander’s thoughtfully crafted drink menu.
Whether you’re a seasoned LEGO® builder or just looking for a fun night out, this is the perfect way to add some festive joy to your week.
Ticket includes a build made of LEGO® bricks and a WANDER drink ticket
-Ages 18+
-Space is limited—grab your spot now and grow your creativity!
Understanding your ADHD Brain: A Conversation over Coffee
Understanding Your ADHD Brain: A Conversation Over Coffee
Led by Megs Crawford, ADHD coach, professional organizer, and host of theOrganizing an ADHD Brainpodcast.
This free community event creates a supportive space for anyone curious about ADHD — or navigating it daily — to discuss what feels challenging in everyday life. Participants are invited to share, listen, or simply learn as the group explores common patterns like overwhelm, freezing, or difficulty with routines.
The session will offer practical, ADHD-friendly tools and simple next steps to help people advocate for themselves at home, at work, or in conversations with others. All levels of familiarity with ADHD are welcome, including those just beginning to explore it.
Free to attend.
All are welcome
PUZ DUZ TRIVIA NIGHT
PUZ DUZ: Trivia Night (monthly)
Get ready to tease your brain and slay the game!
Bring your crew (teams up to 4)
🎁 Prizes for the top teams, laughs, and bragging rights guaranteed
Pick your teammates + Join us for some end of summer fun!
Bella's Truffle Bingo Ball
Hosted by the Berkshires favorite BINGO queen - Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes from Truffles by Tarah and even fiercer vibes.
Supportive Community Gathering
Parents, families, and caregivers of trans*, non-binary, and gender expansive young people are welcome for this peer-driven social support group. Facilitated by Kelly Heck, LICSW, there will be a focus on sharing lived experiences as caregivers, and opportunities to discuss the joys and challenges of supporting our young people in their journeys.
Autumn Phoenix - Live Acoustic Performance
Autumn Phoenix Live Acoustic Performance
Last Sunday of the Month Residency
You may know Autumn as photographer, she is also an award winning singer songwriter!
She will be performing original material (new and old), and some covers.
PUZ DUZ TRIVIA NIGHT
PUZ DUZ: Trivia Night (monthly)
Get ready to tease your brain and slay the game!
Bring your crew (teams up to 4)
🎁 Prizes for the top teams, laughs, and bragging rights guaranteed
Pick your teammates + Join us for some end of summer fun!
Community Potluck
Rainbow Seniors & Stonewall Monthly Potluck
Join Rainbow Seniors and Stonewall for a monthly community potluck at WANDER, held on the first Thursday of each month from 4–6 PM. This welcoming gathering is a space for LGBTQ+ adults and allies to connect, share a meal, and build meaningful community in a relaxed and inclusive environment.
Bring a dish to share (if you’re able), enjoy good conversation, and spend time in a space rooted in care, creativity, and belonging.
Free. All are welcome.
Understanding your ADHD Brain: A Conversation over Coffee
Understanding Your ADHD Brain: A Conversation Over Coffee
Led by Megs Crawford, ADHD coach, professional organizer, and host of theOrganizing an ADHD Brainpodcast.
This free community event creates a supportive space for anyone curious about ADHD — or navigating it daily — to discuss what feels challenging in everyday life. Participants are invited to share, listen, or simply learn as the group explores common patterns like overwhelm, freezing, or difficulty with routines.
The session will offer practical, ADHD-friendly tools and simple next steps to help people advocate for themselves at home, at work, or in conversations with others. All levels of familiarity with ADHD are welcome, including those just beginning to explore it.
Free to attend.
All are welcome
Protest Open Mic
Protest Open Mic with host Robin OHerin
Every Second Wednesday of the Month
Bring Poems, Spoken Word, Songs and more….
FREE AND OPEN TO ALL PEOPLE ALL AGES
COME ONE - COME ALL!!!
Brick & Sip
We’re teaming up once again with Bottomless Bricks to offer an adults-only evening of building. Each month will be a themed build and your ticket also includes a zero-proof beverage from Wander’s thoughtfully crafted drink menu.
Whether you’re a seasoned LEGO® builder or just looking for a fun night out, this is the perfect way to add some festive joy to your week.
Ticket includes a build made of LEGO® bricks and a WANDER drink ticket
-Ages 18+
-Space is limited—grab your spot now and grow your creativity!
Narrative Processing + Liberatory Visioning Workshop
Join us for our monthly Narrative Processing + Liberatory Visioning Workshop
This is a casual, communal gathering hosted by seeing rainbows, where we hold space with writing, reflection, and collective dreaming. Together, we stand intentionally in the liminal space between past and present, drawing on the generative energy of the group and the container we build to nurture a shared sense of liberation.
In this continuing workshop (2nd Sunday of the month), we’ll explore the power of narrative for visioning and healing; though rooted in writing, all mediums and forms of expression are welcome.
This is an open workshop, with cis allies welcomed. Come early to grab a beverage and snack.
Autumn Phoenix - Live Acoustic Performance
Autumn Phoenix Live Acoustic Performance
Last Sunday of the Month Residency
You may know Autumn as photographer, she is also an award winning singer songwriter!
She will be performing original material (new and old), and some covers.
Bella's Bingo Ball
Hosted by the Berkshires favorite BINGO queen - Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes by local bookstore Indie Readery & Records and even fiercer vibes.
Bella's BURROW Bingo Ball
Hosted by the Berkshires favorite BINGO queen - Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes and even fiercer vibes. Prizes will be provided by Beetle Buds.
Autumn Phoenix - Live Acoustic Performance
Autumn Phoenix Live Acoustic Performance
Last Sunday of the Month Residency
You may know Autumn as photographer, she is also an award winning singer songwriter!
She will be performing original material (new and old), and some covers.
Queer Book Club
This month’s pick: Mostly Dead Things by Kristen Arnett. We'll be meeting on Sunday, Oct. 25 at 11 a.m.
Brief description: After the death of her father, Jessa-Lynn must take over her family's unusual business: a taxidermy shop in Florida. While trying to make ends meet, she tries to keep the rest of her family from unraveling in their grief - and reckons with feelings for the woman who also happens to be her brother's wife.
In Paris in the 1950s, a young American man named David begins an affair with a bartender, Giovanni, while his fiancée is away on a trip. Torn between his desire for Giovanni and the promised security of a straight marriage, David faces a difficult decision once his fiancée returns.
Aura Photography at Wander!
Aura Photography at Wander!
Saturday October 24th 3-5 pm
See the colors of your subtle energy field with the Progen Aura Camera 6000! Receive your aura photo and an interpretation handout. Come anytime between 3-5 pm - walk-ins are welcome. Early sign ups get a discount!
Aura Photo and Handout: $36
Sign up online by October 18th- $32
PUZ DUZ TRIVIA NIGHT
PUZ DUZ: Trivia Night (monthly)
Get ready to tease your brain and slay the game!
Bring your crew (teams up to 4)
🎁 Prizes for the top teams, laughs, and bragging rights guaranteed
Pick your teammates + Join us for some end of summer fun!
Listening Session with State Representative Tricia Farley Bouvier for Trans and Non Binary residents
Listening Session with State Representative Tricia Farley Bouvier
for Trans and Non Binary Berkshire County residents, in partnership with seeing rainbows
Monday, October 19th
Session 5-6:30P
Join us at WANDER Berkshires for a listening session with representative Tricia Farley Bouvier for Pittsfield trans and non-binary residents. Please come and share your experience as a trans person in Pittsfield.
Understanding your ADHD Brain: A Conversation over Coffee
Understanding Your ADHD Brain: A Conversation Over Coffee
Led by Megs Crawford, ADHD coach, professional organizer, and host of theOrganizing an ADHD Brainpodcast.
This free community event creates a supportive space for anyone curious about ADHD — or navigating it daily — to discuss what feels challenging in everyday life. Participants are invited to share, listen, or simply learn as the group explores common patterns like overwhelm, freezing, or difficulty with routines.
The session will offer practical, ADHD-friendly tools and simple next steps to help people advocate for themselves at home, at work, or in conversations with others. All levels of familiarity with ADHD are welcome, including those just beginning to explore it.
Free to attend.
All are welcome
Protest Open Mic
Protest Open Mic with host Robin OHerin
Every Second Wednesday of the Month
Bring Poems, Spoken Word, Songs and more….
Our Featured performer for October is Ted DiPietro Jr.
Ted is a versatile musician whose talent spans performing, producing, and building community through music.
come on out and enjoy his eclectic mix of music.
FREE AND OPEN TO ALL PEOPLE ALL AGES
COME ONE - COME ALL!!!
BAC @ Wander: Mini Nature Assemblance Boxes
BAC @ Wander: Mini Nature Assemblance Boxes
1 Saturday, from 10:00am-12:00pm
Description: Join BAC on the second Saturday of each month this fall to explore a fun new technique in a creative community setting. This month invites all levels to exploring assemblage in beautiful cafe setting. Try something new, capture everyday moments and connect with a welcoming creative community. No long term commitment needed!
seeing rainbows narrative processing workshop
seeing rainbows hosts Narrative Processing Workshop
in this workshop, we stand intentionally in the liminal space between past and present. from this vantage point, we gather to draw upon the generative energy of the group with which we gather, and the space we hold together, and from this seed grow this bubble of liberation.
in this continuing workshop at WANDER Berkshires, we will specifically be exploring the power of narratives for both visioning and healing. although we are rooting this practice in writing, all media and forms of expression are welcomed.
REGISTER HERE
cis allies welcomed
The States in Between Tour
Shannon Tehya and Keegan James are continuing their “States in Between” tour with an intimate listening room concert bringing their rootsy pop sounds and light-hearted personalities to WANDER in Pittsfield Massachusetts! Bring a friend and get cozy in the warmest community space in town. You can expect to hear acoustic versions of Shannon and Keegan's greatest hits from their recent individual projects.
Doors at 5 - show at 6!
Monthly Community Potluck
Join Rainbow Seniors and this month’s co-host seeing rainbows for a monthly community potluck at WANDER, held on OCT 1ST ( first Thursday of each month) from 5-7PM.
This welcoming gathering is a space for LGBTQ+ community and allies to connect, share a meal, and build meaningful community in a relaxed and inclusive environment.
Bring a dish to share (if you’re able), enjoy good conversation, and spend time in a space rooted in care, creativity, and belonging.
Free. All are welcome.
Bella's Bingo Ball
Hosted by the Berkshires favorite BINGO queen - Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes and even fiercer vibes.
Autumn Phoenix - Live Acoustic Performance
Autumn Phoenix Live Acoustic Performance
Last Sunday of the Month Residency
You may know Autumn as photographer, she is also an award winning singer songwriter! She will be performing original material (new and old), and some covers.
This month’s featured performer is Hazel Basil.
Hazel is a singer-songwriter based in Northampton, MA. Her music revolves around the strength she finds in community, introspection, and self-acceptance. After realizing she was transgender in 2022, Hazel felt an immense surge of love for her community and music, and has been working to bring friends and strangers alike together over a mutual love of music ever since. Hazel has performed at venues across New England, including the Iron Horse, the Academy of Music, and Club Passim. She is also known locally for her work hosting monthly queer open mics at the Parlor Room in Northampton, MA. Hazel hopes that the self-acceptance and introspection she encourages through her work leads audiences to find more space for complexity, joy, and compassion. In the face of oppression, our joy is more important than ever.
Queer Book Club
This month's pick is Giovanni's Room by James Baldwin. Here's a brief blurb:
In Paris in the 1950s, a young American man named David begins an affair with a bartender, Giovanni, while his fiancée is away on a trip. Torn between his desire for Giovanni and the promised security of a straight marriage, David faces a difficult decision once his fiancée returns.
Silverlake Booking presents Hard Core Music Showcase
SILVERLAKE BOOKING PRESENTS
HARD CORE SHOWCASE
LUNG EATER
SUMMERS IN AUTUMN
DAISY CHAIN
EYES OF APATHY
VIGIL
FRIDAY | SEPTEMBER 25th
DOORS 6P
SHOW 7P
$10 door
ALL AGES
Crafty Karaoke
CRAFT + KARAOKE
THURSDAY SEPTEMBER 24th
6-9PM
Join us every LAST THURSDAY of the month for a double dose of cozy creativity and good vibes!
We’re preparing with a hands-on craft where you’ll make something special to take home.
Then, keep the energy flowing and sing your heart out with Ash during karaoke while you craft, connect, and celebrate community.
Wandering Dance Community Mixer
Wandering Dance Festival
Wednesday, September 23, 2026 | 7:00–9:00 PM
FREE Community Mixer bringing together dance artists, instructors, choreographers, performers, educators, organizations, and community partners from across the region.
Connect with members of the local and regional dance community, learn about creative projects and organizations, exchange ideas, and explore opportunities for collaboration.
Free and open to all. Come connect, share, and help strengthen our region’s dance community.
Complete the RSVP form to guarantee your spot: https://form.jotform.com/262364568004053
GBH News + NEPM Office Hours - What Matters to You?
What Matters to You?
GBH News + NEPM Office Hours
Wed | Sept 23rd 11a-1p
Join GBH News at an upcoming listening session. We want to hear what matters to you, what keeps you up at night, and what makes you proud. Come and meet a reporter to share whats newsworthy in our community -
or drop by to say hello!
Understanding your ADHD Brain: A Conversation over Coffee
Understanding Your ADHD Brain: A Conversation Over Coffee
Led by Megs Crawford, ADHD coach, professional organizer, and host of theOrganizing an ADHD Brainpodcast.
This free community event creates a supportive space for anyone curious about ADHD — or navigating it daily — to discuss what feels challenging in everyday life. Participants are invited to share, listen, or simply learn as the group explores common patterns like overwhelm, freezing, or difficulty with routines.
The session will offer practical, ADHD-friendly tools and simple next steps to help people advocate for themselves at home, at work, or in conversations with others. All levels of familiarity with ADHD are welcome, including those just beginning to explore it.
Free to attend.
All are welcome
BAC at WANDER: Commonplace Visual Journaling
BAC @ Wander: Commonplace Visual Journaling
1 Saturday, from 10:00am-12:00pm
Description: Join BAC on the second Saturday of each month this summer to explore a fun new technique in a creative community setting. This month invites all levels to try visual journaling and sketch in a beautiful cafe setting. Try something new, capture everyday moments and connect with a welcoming creative community. No long term commitment needed!
Protest Open Mic
Protest Open Mic with host Robin OHerin
Every Second Wednesday of the Month
Bring Poems, Spoken Word, Songs and more….
FREE AND OPEN TO ALL PEOPLE ALL AGES
COME ONE - COME ALL!!!
Community Potluck
Rainbow Seniors & Stonewall Monthly Potluck
Join Rainbow Seniors and Stonewall for a monthly community potluck at WANDER, held on the first Thursday of each month from 4–6 PM. This welcoming gathering is a space for LGBTQ+ adults and allies to connect, share a meal, and build meaningful community in a relaxed and inclusive environment.
Bring a dish to share (if you’re able), enjoy good conversation, and spend time in a space rooted in care, creativity, and belonging.
Free. All are welcome.
Autumn Phoenix - Live Acoustic Performance
Autumn Phoenix Live Acoustic Performance
Last Sunday of the Month Residency
You may know Autumn as photographer, she is also an award winning singer songwriter!
She will be performing original material (new and old), and some covers.
Queer Book Club
All are invited, even if you have not read the book!
"We The Animals is a coming-of-age story that follows a half-Puerto Rican, half-white boy and his two brothers as they navigate a tumultuous childhood charged with fierce love, family strife and their own chaotic antics. The unnamed narrator will eventually drift apart from his tight-knit family as he reckons with his sense of self."
Bella's Bingo PLANT Ball
Hosted by the Berkshires favorite BINGO queen - Bella Santarella, this monthly high-energy drag bingo night is $5 a card with fun prizes and even fiercer vibes.
We are teaming up with The Plant Connector to offer the plant prizes of your dreams!
Olivia Maaia live music performance
Olivia Maaia live music performance
SUNDAY | AUGUST 23 | 12-2:00PM
Her set will consist primarily of original compositions, with songs evoking everything from Berkshire summer campfires to angsty romantic breakups.
Come and catch her before she heads off to Boston for the fall!
Olivia Maaia is a 19 year old singer-songwriter who grew up in Washington DC, although was born and currently resides in Pittsfield, MA.
Dre’s Jouvert x Depot After Dark
AUGUST 22nd 8-11PM!
Dre’s Jouvert x Depot After Dark
A Night of Carnival Energy, Culture & Connection
---
Get ready for a one-of-a-kind night as Dre's Global Kitchen and The Weekend Is Never Over (TWINO) join forces to bring Depot After Dark to life with Dre’s Jouvert !
What is Jouvert?
It's the heartbeat of Caribbean Carnival
A sunrise celebration born from resistance, freedom, and the joy of a people who turned struggle into culture, music, and movement. It's about unity, pride, and pure, unstoppable vibes.
---
We’re bringing that energy straight to the alley with:
🎭 Caribbean Carnival dancers from Berkshire Brazil
🍛 Authentic island food by Dre’s Global Kitchen
🎶 Nonstop soca & dancehall beats from NYC's own DJ Shyboogie & DJ Shy Mac
---
Dress Code: Rep your roots! Come dressed in your country's colors or flag. This is a celebration of all Caribbean people and the spirit that moves us
So wear your heritage with pride !
---
Event Details
📅 Date: Saturday, August 22nd, 2026
⏰ Time: 6:00 PM – 11:00 PM
📍 Location: 34 Depot St, Pittsfield (between Wander, Tito's, and Crawford Square, right where Dre's Global Kitchen lives).
🎟️ Entry: $15 suggested / pay what you can
A huge thank you to Downtown Pittsfield for the continued support. Let's make this one for the books!
Back to School Fair
Join Berkshire Pride and Berkshire Trans Exchange for our annual back-to-school event on Saturday August 22nd from 12-2pm at Wander. This event features free school supplies, gender-affirming clothing and resources, as well as free haircuts! This year, we are partnering with Drag Story Hour's Bingo 4 Books Fundraiser, so there will be even more fun and excitement!
Poetry Reading with Melinda Goodman
Join Rainbow Seniors on Thursday August 20th from 6-7:30pm to hear Melinda Goodman read from her new book of original poems “Your Forever Heifer Princess”.
“Melinda Goodman is a marvelous poet, her work is full of wit and reassuring amounts of truth-telling, spiced with sparkling insights. I recommend her written words and her poetry video recordings.” — Judy Grahn
Melinda Susan Goodman has been teaching at Hunter College in New York City since 1987. She was a founding member of the Audre Lorde Women’s Poetry Center and was a former member of the editorial collective of Conditions, the world’s first Lesbian literary journal. Her poems have appeared in LGBTQ journals and anthologies and she was an early recipient of an Astraea Award for Lesbian poets. Goodman holds an MA from NYU and an MFA from Columbia University where she received a fellowship citation. In 2012 she was awarded a fiction fellowship from the New York Foundation on the Arts.
PUZ DUZ TRIVIA NIGHT
PUZ DUZ: Trivia Night (monthly)
Get ready to tease your brain and slay the game!
Bring your crew (teams up to 4)
🎁 Prizes for the top teams, laughs, and bragging rights guaranteed
Pick your teammates + Join us for some end of summer fun!