Elevate your weeknight above Gloucester Harbor. Join us on the Birdseye Rooftop for live music, handcrafted cocktails, and golden hour views stretching from the working waterfront to downtown Gloucester, all […]
$20
35 events found.
Events
Calendar of Events
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1 event,
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1 event,
Elevate your weeknight above Gloucester Harbor. Join us on the Birdseye Rooftop for live music, handcrafted cocktails, and golden hour views stretching from the working waterfront to downtown Gloucester, all […]
$20
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2 events,
Visit downtown Gloucester’s farmers market, the Backyard Growcery, brought to life by food equity nonprofit Backyard Growers every Wednesday, 2:30-6:30pm, at Burnham’s Field. The Backyard Growcery brings fresh, local food […]
Elevate your weeknight above Gloucester Harbor. Join us on the Birdseye Rooftop for live music, handcrafted cocktails, and golden hour views stretching from the working waterfront to downtown Gloucester, all […]
$20
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6 events,
How to See the Schooners with Cape Ann Cruises Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water. The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun! See […]
$100
Explore the art of painting color and light with water-based oils in a small group setting. Environmentally friendly and a bit faster drying, water-based oils offer the experience of traditional […]
Elevate your weeknight above Gloucester Harbor. Join us on the Birdseye Rooftop for live music, handcrafted cocktails, and golden hour views stretching from the working waterfront to downtown Gloucester, all […]
$20
From John Hays Hammond Jr.’s attempts to communicate with supernatural entities using a Faraday Cage to Irene Fenton Hammond’s extensive astrological writings under a mysterious pen name, this 55-minute, fully-guided […]
$27.50 – $35.00
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6 events,
What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives of one Gloucester family and the changing history of Cape Ann. This docent-led experience invites visitors to look closely at the details that transform a […]
Free with General Admission
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Main Street Gloucester 1-160 Main Street Gloucester MA 01930 5 PM Streets closed off to traffic & parking 6 PM Music Stages Open (x3) *Also look for these Special Guests on Main Street: Balloon Twisting by TBD Cape Ann Vernal Pond Team Reptiles (Captain Jack-TBD) Face Painting by Miss Wendy 6:15 PM Busker-TBD 7:30 PM […]
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We are back under the big tent at Windhover for Americana night - in keeping with our goal of elevating local talent, this night features Wood and Bone, a North Shore favorite known for complex and bluesy toe-tapping Americana, with opening act Kicked Off the Bus, Gloucester’s own wildly talented group of students.
$25
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9 events,
From stick figure doodlers to first-rate talents, join us for a seaside, En Plein Air sketch class with Sue Wheeler of Arts Abound in Magnolia. All skill levels are welcome! This two-hour session includes a 30-minute beginner sketch lesson. All you need to bring is a sketchbook, pencils, a ruler, and an eraser. Please note: […]
$25.00
Join noted raconteur Phil Storey for this "fun filled" Phil Facts about Gloucester's deep literary past! Phil Storey is a local local historian, noted raconteur, and master storyteller. He developed this engaging literary walking tour during Gloucester’s 400+ celebration and is excited to continue hosting it in partnership with the Gloucester Writers Center. Gloucester has […] 
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […] |
4 events,
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Join us for the Gloucester Schooner Festival Paint Out on Sunday, September 6, 2026, and capture the beauty of one of Cape Ann's most iconic events. From majestic schooners and colorful maritime flags to blooming dahlias, the sparkling ocean, historic waterfront, and bustling festival atmosphere, inspiration will be everywhere. Artists will paint throughout the morning, […]
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
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The closing concert of Folk Week, we have Ramon Tasat playing Sephardic songs in the beautiful St. Anthony's by the Sea. Vocalist, musician, and gifted entertainer Ramón Tasat thrills audiences with his magnificent tenor voice and unforgettable guitar arrangements. Ramón sings in Hebrew, Ladino, Spanish, Italian, and English, and specializes in Sephardic music.
$25
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0 events,
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1 event,
Visit downtown Gloucester’s farmers market, the Backyard Growcery, brought to life by food equity nonprofit Backyard Growers every Wednesday, 2:30-6:30pm, at Burnham’s Field. The Backyard Growcery brings fresh, local food to our community while supporting small-scale farms and up-and-coming food businesses. It’s more than just a market—it’s a space to connect, learn, and grow together. […] |
5 events,
From stick figure doodlers to first-rate talents, join us for a seaside, En Plein Air sketch class with Sue Wheeler of Arts Abound in Magnolia. All skill levels are welcome! This two-hour session includes a 30-minute beginner sketch lesson. All you need to bring is a sketchbook, pencils, a ruler, and an eraser. Please note: […]
$25.00
Explore the art of painting color and light with water-based oils in a small group setting. Environmentally friendly and a bit faster drying, water-based oils offer the experience of traditional oil paints without the necessity of solvents. Learn to see and use color relationships to interpret the effects of light. Join us on Thursday afternoons […]
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Tech on the Horizon: Behind the Big Top – Score Analysis & Live Tech in Circus Music w/ Peter Bufano
Tech on the Horizon: Behind the Big Top – Score Analysis & Live Tech in Circus Music w/ Peter Bufano
As part of our Tech on the Horizon series, join us in the community room for: Behind the Big Top: Score Analysis & Live Tech in Modern Circus Music w/ Peter Bufano. As part of our Technology on The Horizon series, step right up for a fast-paced, 75-minute peek behind the curtain into the illusionary […] |
8 events,
Calling all artists! Don’t miss your chance to participate in the 2026 Sawyer Free Library Art Auction, benefiting the Sawyer Free Library Building Restoration Campaign. Artists may submit up to two works for consideration. Artwork should be priced as it would be for any sale, with a maximum framed size of 18" x 22" and […] 
Over the course of three days, 9/11-9/13, a variety of talks, walks, and other activities will explore the downtown neighborhood around Gloucester City Hall which has been the cultural, educational, and civic center of the city since the 1800s. Learn about the past and present of the major institutions of the area, including the Library […]
$25.00
What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives of one Gloucester family and the changing history of Cape Ann. This docent-led experience invites visitors to look closely at the details that transform a […]
Free with General Admission
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Dive into the remarkable life and art of Nell Blaine, an artist whose journey transcends the boundaries of abstraction and figuration, illuminating the vibrancy of the world around us. From the bustling streets of New York City to the serene banks of the Seine in Paris and the colorful landscapes of Mexico and Gloucester Harbor, […] |
4 events,
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Discover the power of color in the natural world during this two-hour outdoor workshop led by artist and author Kimberly Collins Jermain. Set on the CAM Green, this hands-on session introduces participants to working with pastel through an exercise from Jermain’s newly published book The Nature of Color, which presents her innovative, nature-based approach to […]
$45.
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
Over the course of three days, 9/11-9/13, a variety of talks, walks, and other activities will explore the downtown neighborhood around Gloucester City Hall which has been the cultural, educational, and civic center of the city since the 1800s. Learn about the past and present of the major institutions of the area, including the Library […]
$25.00
|
4 events,
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
Over the course of three days, 9/11-9/13, a variety of talks, walks, and other activities will explore the downtown neighborhood around Gloucester City Hall which has been the cultural, educational, and civic center of the city since the 1800s. Learn about the past and present of the major institutions of the area, including the Library […]
$25.00
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory of his mother, Spencer dives into the mystery of his youth and uncovers the true identity behind his estranged father. Journey through time and space […]
$18 – $74
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0 events,
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1 event,
Since its first iteration in 2013, the Gloucester Writers Center’s “Moth”-like storytelling showcase has grown from a cozy evening among friends to one of the city’s most-loved events, featuring storytellers from Gloucester and beyond telling their true stories live on stage without notes. Coming up on September 15: Eight talented storytellers will reveal their big […] |
5 events,
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Artists participating in the 2026 Sawyer Free Library Art Auction are invited to drop off their accepted artwork. Where: Community Room, Sawyer Free Library Artwork Drop-Off: Wednesday, September 16 | 1:00–5:30 PM Please make sure all artwork is ready to hang. Can’t make the scheduled drop-off time? To arrange an alternative day, please contact Christine […]
Visit downtown Gloucester’s farmers market, the Backyard Growcery, brought to life by food equity nonprofit Backyard Growers every Wednesday, 2:30-6:30pm, at Burnham’s Field. The Backyard Growcery brings fresh, local food to our community while supporting small-scale farms and up-and-coming food businesses. It’s more than just a market—it’s a space to connect, learn, and grow together. […]
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A Western exhibition at a seaside New England castle? That's exactly what makes this temporary exhibition so special. Join Hammond Castle Museum for an exclusive opening celebration of "Brave-Too-Much": The Legend of John Coffee Hays, an original temporary exhibition presented in partnership with the Texas Ranger Hall of Fame and Museum in Waco, Texas. Through […]
$15.00
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6 events,
Join Us Mid-Day for Artful Conversations Take a midday pause and experience one work of art in depth. Artful Conversations are informal, docent-led gallery experiences that invite visitors to slow down, look closely, and engage in thoughtful conversation. Each session features a work of art or object that is new to view—whether a recent acquisition […]
$25
Explore the art of painting color and light with water-based oils in a small group setting. Environmentally friendly and a bit faster drying, water-based oils offer the experience of traditional oil paints without the necessity of solvents. Learn to see and use color relationships to interpret the effects of light. Join us on Thursday afternoons […]
From John Hays Hammond Jr.’s attempts to communicate with supernatural entities using a Faraday Cage to Irene Fenton Hammond’s extensive astrological writings under a mysterious pen name, this 55-minute, fully-guided specialty tour sets the stage for a fun and informative seasonal experience unlike any other. The dramatic, Gothic-inspired architecture of the Museum and the twilight […]
$27.50 – $35.00
|
6 events,
What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives […]
Free with General Admission
Odysseus, king of Ithaca, embarks on a perilous journey to return home after the Trojan War. Crossing the Mediterranean Sea with his fellow soldiers, they soon find themselves battling not only the elements, but an array of deadly obstacles and mythical creatures along the way. Directed by Christopher Nolan (The Dark Knight, Inception, Oppenheimer). Starring […]
$14
Join us on the water during the Centennial Season of Schooner Adventure! Now celebrating 100 years, Adventure invites you to experience Gloucester Harbor from the deck of a true National […]
$60
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9 events,
-
Residents and visitors are invited to take a closer look at Gloucester’s urban forest during a free guided Tree Walk & Talk at 9 a.m. Saturday, Sept. 19, beginning at […]
Join noted raconteur Phil Storey for this "fun filled" Phil Facts about Gloucester's deep literary past! Phil Storey is a local local historian, noted raconteur, and master storyteller. He developed this engaging literary walking tour during Gloucester’s 400+ celebration and is excited to continue hosting it in partnership with the Gloucester Writers Center. Gloucester has […]
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio […] |
4 events,
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory of his mother, Spencer dives into the mystery of his youth and uncovers the true identity behind his estranged father. Journey through time and space […]
$18 – $74
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AFTERLIFE MEDIUM EVENT Enjoy an intimate evening of mediumship messages with Endorsed Afterlife Medium Lauren Robbins, featured on The List TV, Married at First Sight TV Show (Boston), The Lady of the Dunes Documentary, and more. Lauren will walk around the room to deliver messages from those who wish to come through with evidential information […]
$54
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0 events,
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0 events,
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2 events,
Visit downtown Gloucester’s farmers market, the Backyard Growcery, brought to life by food equity nonprofit Backyard Growers every Wednesday, 2:30-6:30pm, at Burnham’s Field. The Backyard Growcery brings fresh, local food to our community while supporting small-scale farms and up-and-coming food businesses. It’s more than just a market—it’s a space to connect, learn, and grow together. […]
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory of his mother, Spencer dives into the mystery of his youth and uncovers the true identity behind his estranged father. Journey through time and space […]
$18 – $74
|
8 events,
Join Us Mid-Day for Artful Conversations Take a midday pause and experience one work of art in depth. Artful Conversations are informal, docent-led gallery experiences that invite visitors to slow down, look closely, and engage in thoughtful conversation. Each session features a work of art or object that is new to view—whether a recent acquisition […]
$25
Explore the art of painting color and light with water-based oils in a small group setting. Environmentally friendly and a bit faster drying, water-based oils offer the experience of traditional oil paints without the necessity of solvents. Learn to see and use color relationships to interpret the effects of light. Join us on Thursday afternoons […]
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We Love Greater Cape Ann and work hard to help support our Community in many ways. Your generous bidding will help the Chamber build for the future of this special place where we live, work and play. Live Auction/Silent Auction Fund the Future Paddle Raise Passed Hors d'Oeuvres, Plated Dinner, Cash Bar ❤ compete for […]
$100 – $900
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5 events,
What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives of one Gloucester family and the changing history of Cape Ann. This docent-led experience invites visitors to look closely at the details that transform a […]
Free with General Admission
Join us on the water during the Centennial Season of Schooner Adventure! Now celebrating 100 years, Adventure invites you to experience Gloucester Harbor from the deck of a true National Historic Landmark. Built in 1926 and lovingly preserved by generations of supporters, Adventure remains one of the last surviving Grand Banks dory fishing schooners in […]
$60
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Blues icon. Soul man. Rock and roller. Robert Cray is all these things – and more. The Georgia born, Washington-raised musician first picked up a guitar after seeing The Beatles on TV then, having witnessed Jimi Hendrix perform in Seattle, determined that his destiny would also follow a similar path. And so he has: across […]
$49.50 – $176.00
|
8 events,
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio […]
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory […]
$18 – $74
-
Join us for a cozy fall afternoon at our Autumn Market Pop-Up, a small, community-style craft fair featuring local makers, handmade goods, and seasonal treats. Set in a warm backyard […] |
5 events,
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio […]
-
Join us for the annual Fall Family Fest! This free community event is perfect for all ages and features a bouncy house, games, face painting, music, and a photobooth. Enjoy […]
Free with Pre-Registration
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory […]
$18 – $74
|
|
0 events,
|
0 events,
|
3 events,
Visit downtown Gloucester’s farmers market, the Backyard Growcery, brought to life by food equity nonprofit Backyard Growers every Wednesday, 2:30-6:30pm, at Burnham’s Field. The Backyard Growcery brings fresh, local food to our community while supporting small-scale farms and up-and-coming food businesses. It’s more than just a market—it’s a space to connect, learn, and grow together. […]
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1926: A Year in the Life of Hammond and His Castle Wednesday, September 30th 5:30 pm–7:30 pm Evening program: 5:30 pm–6:00 pm Networking 6:00 pm–7:30 pm Presentation & Discussion Light refreshments will be served. One hundred years ago, John Hays Hammond Jr. embarked on one of the most ambitious projects of his life: building Hammond […]
$15
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Cabot Movie Party events are a little extra: enjoy specialty drinks, photo ops, contests and other on-theme activities before the film! In tribute to the late great Dolly Parton, Steel Magnolias returns to the big screen at The Cabot. M’Lynn (Sally Field) is the mother of bride-to-be Shelby Eatenton (Julia Roberts), and as friend Truvy […]
$13.50 – $16.50
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7 events,
Embrace the transformative energy of Autumn to pursue your artistic vision. Explore the art of painting color and light with water-based oils in a small group setting. Learn to see and use color relationships to interpret the effects of light.
From John Hays Hammond Jr.’s attempts to communicate with supernatural entities using a Faraday Cage to Irene Fenton Hammond’s extensive astrological writings under a mysterious pen name, this 55-minute, fully-guided specialty tour sets the stage for a fun and informative seasonal experience unlike any other. The dramatic, Gothic-inspired architecture of the Museum and the twilight […]
$27.50 – $35.00
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Wines and pairings that make you go wow. 🍷 Join us Thursday, October 1 at 6:30PM for an intimate four-course wine dinner featuring acclaimed Australian winery Mollydooker Wines. Meet Luke Marquis, son of owner Sarah Marquis, and discover the stories behind each unforgettable pour, thoughtfully paired with a four-course menu. October 1 | 6:30PM Four […]
$120
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4 events,
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Ghosts of Jupiter, a New England-based band, has a rich history built on a foundation of progressive rock and psychedelic soundscapes. Led by current moe. keyboardist and founding member of Percy Hill, Nate Wilson, Ghosts of Jupiter formed in 2011. Their self-titled debut was met with regional success and critical acclaim, leading to live performances […]
$29.00
What can a house tell us about the people who lived there? Step inside the Capt. Elias Davis House and discover how architecture, craftsmanship, and everyday objects reveal the lives of one Gloucester family and the changing history of Cape Ann. This docent-led experience invites visitors to look closely at the details that transform a […]
Free with General Admission
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Elizabeth Bish was granted Rocky Neck Art Colony's Invitational Artist Residency for the month of October this year. She will give a public talk about her work at the Cultural Center on Rocky Neck on October 2 at 6:00 pm. She will be painting at her studio in the Amend Bish Art Gallery at 51 […] |
7 events,
Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike! 
Cape Ann Plein Air celebrates 10 extraordinary years! To commemorate our tenth year we have invited 36 award-winning artists to paint all week in five stunning Massachusetts communities—Gloucester, Rockport, Essex, Ipswich, & Manchester-by-the-Sea. Be part of this milestone moment for the Northeast’s leading plein air event. Celebrate art with us. Visit capeannpleinair.org to explore our […]
From stick figure doodlers to first-rate talents, join us for a seaside, En Plein Air sketch class with Sue Wheeler of Arts Abound in Magnolia. All skill levels are welcome! This two-hour session includes a 30-minute beginner sketch lesson. All you need to bring is a sketchbook, pencils, a ruler, and an eraser. Please note: […]
$25.00
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
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Raise a stein and set sail for a festive waterfront celebration at our Oktoberfest Harbor Cruise! Join us on Saturday, October 3rd from 1:00PM–4:00PM for an afternoon filled with sweeping […]
$69
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7 events,
Celebrate the 10th anniversary of Cape Ann Plein Air, October 3–11, 2026, a beloved annual festival welcoming artists to paint Gloucester and Cape Ann en plein air. Enjoy live painting, special exhibitions, artist demos, and opportunities to meet and collect work from participating painters. A must-see week for art lovers and visitors alike!
Michalak Fine Art Open to the public throughout the summer fall and holiday season. Come check out the work and process nationally recognized contemporary oil painter Vanessa Michalak. Her studio has been located at 77 Rocky Neck Ave for the past five years. Her work was featured in New American Paintings issue #110. She was […]
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NO SITTER NECESSARY: K-POP DANCE PARTY - DANCE BATTLE IS COMING TO THE CUT LIVE! You’ve been playing the soundtrack in the car line. Singing it at home. Dancing in the kitchen. Now take it to the dance floor. After packed dance floors and viral moments for the K Pop Parties at The Cut Live, […] 
Inspired by the true story of Beverly's beloved gray seal, Shoebert's Unfinished Journey is a joyful new family operetta by Arpeggione Ensemble. When Shoebert the seal found his way to a former mill pond, he unexpectedly galumphed into the world of another Schubert—composer Franz Schubert, whose songs celebrate mills, water, and fish. In Arpeggione’s heartwarming […] |