View the Gloucester Schooner Festival Aboard the Wejack with Cape Ann Cruises
2026-09-03 - 2026-09-07 | Cape Ann Cruises, 63 ROGERS STREET, Gloucester, M, 01930, United States
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 the Calendar and schedule of events below to learn more about our trips offered for the Schooner Festival. The Wejack is a classic power/fishing vessel that you’ll fall in love with, and is not a schooner., but is the perfect spectator boat to get the best views.
Schedule of Events – Cruise Tickets
Thursday, September 3rd, 2026
Schooner Challenge Race -5:30-7:30PM – Buy Tickets
Friday, September 4th, 2026
See the Schooners & Scenic Harbor Tour 12:00 PM – 1:30 PM – Buy Tickets
See the Schooners & Scenic Harbor Tour 3:30 PM – 5:00 PM – Buy Tickets
See the Schooners, Sunset & Scenic Harbor Tour 6:00 PM – 7:30 PM – Buy Tickets
Saturday, September 5th, 2026
See the Schooners & Scenic Harbor Tour 12:00 PM – 1:30 PM – Buy Tickets
See the Schooners & Scenic Harbor Tour 3:30 PM – 5:00 PM – Buy Tickets
Schooner Festival Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM 7:30PM – details & tickets
8PM – FIREWORKS Cruise Gloucester Harbor – Departs 8:00PM details & tickets
Sunday, September 6th, 2026
Parade of Sail Cruise Departs at 9:30 AM details & tickets
Mayor’s Cup Race – Departs at 12:30 PM details & tickets
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 3:30 PM details & tickets
See the Schooners at Sunset – Departs at 6 PM details & tickets
Monday, September 7th, 2026 – LABOR DAY
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 12 PM details & tickets
See the Schooners – Scenic Gloucester Harbor Cruise Departs at 3:30 PM details & tickets
See the Schooners at Sunset – Departs at 6 PM details & tickets

Birdseye Rooftop Live Music Access
2026-09-03 18:00 - 21:00 (America/New_York) | Beauport Hotel Gloucester, 55 Commercial Street, Gloucester, MA, 01930, United States
Bringing live music every Sunday-Thursday on the Birdseye Rooftop at Beauport Hotel with craft cocktails and unbeatable views.
Elevate your weeknight above Gloucester Harbor. Join us on the Birdseye Rooftop for live music by Dis N Dat Band, handcrafted cocktails, and golden hour views stretching from the working waterfront to downtown Gloucester, all paired with relaxed rooftop vibes and a sunset soundtrack to carry you into the evening. Slip into the pool or unwind in the hot tub as the sun sets and the evening settles in. This is your midweek moment, six stories above it all.
Rooftop Evening Pass begins at 6:00PM. Swimsuits encouraged.
This event is 21+ adults only. General Admission starts at $20 and does not include food and beverage. *Complimentary to hotel guests
Tickets are non-refundable. Events are rain or shine unless the rooftop closes due to inclement weather. Any closure decisions are made by Beauport management at 2:00PM the day of the event; guests will be notified by email.

Spiritualism Tours by Candlelight at Hammond Castle Museum
2026-09-03 18:00 - 21:00, 2026-09-10 18:00 - 21:00, 2026-09-17 18:00 - 21:00 | Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA, 01930, United States
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 atmosphere are enhanced by the light of handheld electronic lanterns throughout your tour.
New in 2026: Extended Hours and Midnight Tours
For the first time, Hammond Castle Museum is offering its popular Spiritualism Tours by Candlelight during extended late-night hours–including a midnight tour–on October 22nd and 29th—a one-of-a-kind experience for those celebrating the Halloween season on the North Shore!
Admission:
July, August, & September: $27.50.
October: $35.
Museum Member savings apply.
Please be mindful when processing your reservation to select the correct reservation date and corresponding admission price.

Gloucester Block Party #3
2026-09-04 18:00 - 22:00 | Main Street, Gloucester, MA 01930, Gloucester, M, 01930, United States
Main Street, Downtown Gloucester comes alive when the Street is closed off and we have live music, street performers, vendors, food vendors and more!
Many of our Shops and Businesses on Main Street will be open for business and welcoming Party goers. Other Gloucester businesses and non-profits will be represented on the Street as well. We can promise a night full of Live music, great food and fun activities with lots of local flavor!
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 Busker-TBD

Sunset Sessions at the Birdseye Rooftop
2026-09-04 19:00 - 22:00 | Beauport Hotel Gloucester, 55 Commercial Street, Gloucester, MA, 01930, United States
Enjoy the weekend in style at Sunset Sessions. An evening of vibrant energy, coastal glamour, and unforgettable harbor front views at Beauport Hotel’s Birdseye Rooftop.
Join us during our 10th year by the sea, every Friday and Saturday evening for a lively celebration featuring DJ entertainment from The 617 Event Group. Dance as the sun sets over Gloucester Harbor, sip handcrafted cocktails, and soak in the atmosphere high above the water. Feeling bold? Bring your suit and take a dip in the pool or hot tub. This event is for guests 21+.
General Admission starts at $30 and does not include food or beverage.
VIP Premium Lounge Tables are $300 and include entry and premium seating for four. For a more elevated experience, reserve one of our VIP Premium Lounge Tables on the Harbor View side of the rooftop. These exclusive tables include a bottle of Veuve Clicquot Yellow Label (inclusive of tax and gratuity)—perfect for toasting the night in style.
Tickets are non-refundable. This event is rain or shine unless the rooftop is closed due to inclement weather, as determined by Beauport management by 2PM on the day of the event. Guests will be notified via email.

Sweeney Todd: The Demon Barber of Fleet Street
2026-09-04 19:30 - 21:30, 2026-09-05 19:30 - 21:30, 2026-09-06 19:30 - 21:30, 2026-09-11 19:30 - 21:30, 2026-09-12 19:30 - 21:30, 2026-09-13 19:30 - 21:30, 2026-09-18 19:30 - 21:30 | Sophia Gordon Center for Creative and Performing Arts, 356 Lafayette Street, Salem, MA, 01970, United States
Salem State theatre celebrates 50 years of theatrical excellence with its production of Stephen Sondheim’s dark, witty and Tony Award-winning tale of love, murder and revenge.
Sweeney Todd has become a bloody, worldwide success since being awarded eight Tony’s, (including Best Musical), for its Broadway premiere. Stephen Sondheim’s and Hugh Wheeler’s (A Little Night Music, Pacific Overtures) tasty, thrilling, theatrical treat has simultaneously shocked, awed and delighted audiences across the world.
An infamous tale, Sweeney Todd, an unjustly exiled barber, returns to nineteenth century London, seeking vengeance against the lecherous judge who framed him and ravaged his young wife. The road to revenge leads Todd to Mrs. Lovett, a resourceful proprietress of a failing pie shop, above which, he opens a new barber practice. Mrs. Lovett’s luck sharply shifts when Todd’s thirst for blood inspires the integration of an ingredient into her meat pies that has the people of London lining up… and the carnage has only just begun!
FOR MATURE AUDIENCES
Music and Lyrics by Stephen Sondheim
Book by Hugh Wheeler
Directed by Peter Sampieri
April 17, 7:30 pm
April 18, 7:30 pm
April 19, 2 pm
April 24, 7:30 pm
April 25, 7:30 pm
April 26, 2 pm
TICKETS
$15 general/$10 seniors/free for all students with student ID and under 18.
Friday, April 24 is SALEM NIGHT. Free admission for Salem residents. This event takes place in our mainstage theater, no advance reservation required.
Tickets are available at: https://salemstatetickets.universitytickets.com/w/
For access and accommodation information, visit https://www.salemstate.edu/access or email access@salemstate.edu.

Mighty Mystic with Double Tiger
2026-09-04 20:00 - 22:00 | The Cut, 177 Main Street , Gloucester, MA, 01930, United States
Mighty Mystic is considered as one of the leaders in the international reggae scene and is a box office draw at venues and a staple at festivals. The Jamaican born U.S. based artist has 5 highly acclaimed albums 4 of which charted top 10 on Billboard and iTunes. He is labeled as a touring machine with roughly 40 tours equaling thousands of concerts and a career spanning two decades. His high flying, stage diving, brand of reggae music is electrifying and has been captivating audiences everywhere. He has gone from being a fan of reggae music to being a major contributor to the art. Mighty Mystic came on the scene in 2006 after scoring back-to-back international hits with “Riding on the Clouds” and “Revolution”. However, it wasn’t until the release of his first album “Wake up the World” (2010) that he became a household name. “Wake up the World” was a chart-topping album with guest appearance by reggae icon Shaggy. Mystic continues to wake up the world with energy and passion and a brand of his own which he emphatically calls “Hard Roots”.
FUN FACT: Mighty Mystic is also the younger brother of current Jamaican Prime Minister the Honorable Andrew Holness. When asked, does being the brother of Prime Minister Holness have any impact on your music? Mystic simply says “Andrew has a job to do and so do I, impact or not we both have our own mission to complete”.
THE EARLY YEARS
Mighty Mystic was born Kevin Mark Holness in the farming community of Goshen, St. Elizabeth, Jamaica to parents Morris & Sonia Holness. As a child, Kevin showed early interest in his native island’s music. It was common to hear him singing the latest tunes while imitating the actions of popular reggae artists. When Kevin was 9, the family left Goshen and relocated to Boston. Though oceans apart Kevin never lost the passion for his beloved reggae music. Kevin alongside his brother Stephen began performing at school talent shows, outdoor gatherings and anywhere a mic was on display and quickly made a name for themselves as the “reggae rappers”. Soon after the brothers formed their first band the “Thunder Band”. Kevin became “Mystic” as it was his dads nickname and also the name of the area in Boston where he lived. With Mystic on vocals and Stephen on the lightening sharp guitar the brothers would score a National hit (Riding on the Clouds) and a Global hit (Revolution) on their two first releases. This early success and family bond would be the foundation of which carefully crafted reggae music would flow.
MYSTIC OF TODAY
Though his brother Stephen has since retired, Mighty Mystic has continued to carry the reggae torch. And is now a Globally respected and sought-after artist on the reggae scene. His brand of “HARD ROOTS” with his high energy stage performance has been a magnet for the enthusiastic reggae fan base. He has managed to hold firm to his Jamaican roots while adding elements of Hip Hop and Rock giving Mystic his own identifiable sound. To date Mighty Mystic has released 5 successful albums Wake up the World 2010, Concrete World 2014, The Art of Balance 2016, Enter the Mystic 2019 and Giant 2022. Many of his releases have become cult like favorites within the global reggae genre. He has come a long way from performing at school talent shows to now sharing the stage with some of the greats like Ziggy Marley, Steel Pulse, Damian Marley, Buju Banton, Stephen Marley, Shaggy, SOJA, Toots and the Maytals, Collie Buddz, Sean Paul, Lee Scratch Perry, Barrington Levy, The Wailers, John Brownʼs Body, Dirty Heads Third World, Freddie McGregor, Capleton and the list goes on… Whether club, festival or TV you can be sure to be entertained by the vibes provided by Mighty Mystic. Be on the lookout for his up-coming 2022 “Giant” Album release world tour.
DOUBLE TIGER
Double Tiger (Jay Spaker) is an acclaimed producer, vocalist, and multi-instrumentalist who has become a central figure in the modern American reggae and dub scene. Originally gaining prominence as a key collaborator and producer for the influential label Dub-Stuy Records, he is known for heavily integrating sound system culture into contemporary roots aesthetics.
As a solo artist and front-man, his music blends smooth, melodic vocals with heavy, 1980s-inspired steppers and rub-a-dub riddims. He is also a long-time guitarist and vocalist for John Brown’s Body, firmly establishing his credentials within the progressive reggae-rock landscape.

En Plein Air Sketch Classes with Sue Wheeler
2026-09-05 09:30 - 11:30, 2026-09-10 13:00 - 15:00 | Hammond Castle Museum, 80 Hesperus Avenue, Gloucester, MA, 01930, United States
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: watercolors, pastels, oils, or acrylics are not permitted on the Museum grounds.
Attendees who wish to tour the Hammond Castle Museum after this class are entitled to a 20% discount on a self-guided tour. Tour tickets may be purchased in the Museum Shop before 2:30 pm on the day of this class.
Class Schedule:
Thursday Plein Air Sketch classes: 1:00 pm – 3:00 pm.
May:14
June: 11
July 23: (6 – 8 pm)
August: 6
September: 10
October: 8
Saturday En Plein Air Sketch classes: 9:30 am- 11:30 am.
May: 9
June: 20
July:18
August: 1
September: 5
October: 3
All classes are $25 each. Museum Member savings apply.
Weather-dependent; classes may be canceled, and reservations will be refunded if necessary.
About Sue Wheeler:
Sue has a lifetime of making art through various mediums from delectable pastries to abstracts in pastels, watercolor, and acrylics. She enjoys using her creative flair in quilting and interior design as well.
Sue graduated from the University of Denver with a Bachelor’s in business with a focus on hospitality management and earned an associate’s degree from the Culinary Institute of America. Following her tenure as a pastry chef in New Hampshire, Sue returned to school for a certificate in graphic design and put her talents to use as a designer in the book publishing and art publishing industries in Vermont. In early 2019, Sue opened her own gallery and studio, Arts Abound in Magnolia Village, MA, as an artistic haven for local artists. Through the gallery, over 30 artists featured their creative works, ranging from paintings, hand-painted silk scarves, silver jewelry, and more. Sue also ran many workshops and classes featuring many of the artists. Often, Sue would work late into the night, painting in her Arts Abound studio. After closing the gallery in 2022, Sue continued to offer the often sold-out painting classes, taught by some of the Arts Abound artists.
Sue has studied under numerous artists to learn watercolor, acrylic painting, cold wax & oil, and collage. Her goals for the Hammond Castle Museum sketch classes are to engage those who are new to the world of art and reinvigorate those who haven’t picked up a blank canvas or sketch pad in a long time. Sue’s philosophy on the creative process encourages you to be less concerned about the final product and instead to enjoy the journey of creativity and get lost in the moment. Once you find yourself in your work, you may just be surprised!

Barry Goudreau's Engine Room
2026-09-05 20:00 - 22:00 | The Cut, 177 Main Street , Gloucester, MA, 01930, United States
Join guitarist Barry Goudreau, formerly of the band “Boston”, to celebrate the 50th anniversary of the debut record that went on to sell 17 million albums. His awesome seven piece band of seasoned musicians, the “Engine Room”, will take you through the hits on the first two records as well as his other bands, and classic rock favorites. Don’t miss out!

Vintage Base Ball
2026-09-06 11:00 - 17:00, 2026-09-13 11:00 - 17:00 | Spencer-Peirce-Little Farm, 5 Littles Lane, Newbury, M, 01951, United States
It’s Base Ball, 1864 style at Spencer Peirce Little Farm! These fun, historically accurate games feature underhand pitching without gloves. A ball bounced once and caught is an out! Snacks, baseballs, and cards are available for purchase. Come and see for yourself how “America’s favorite pastime” was played in the 1860s. The teams competing are based on actual nineteenth-century baseball clubs from New England.
The Essex Base Ball Organization is a nonprofit “vintage base ball” group that plays the game as it was played in the 1860s. They are based out of Newbury, Massachusetts, and have four teams. They teach the history of baseball through games and demonstrations, offering youth clinics and lectures on baseball history at historical societies, libraries, and other civic organizations.
See HNE website for first pitch times; triple headers start at 11 AM, doubles at noon.

Gloucester Stage Company presents MOON MAN WALK by James Ijames
2026-09-10 19:30 - 2026-09-11 21:00, 2026-09-11 19:30 - 2026-09-12 21:00, 2026-09-12 19:30 - 2026-09-13 21:00, 2026-09-13 14:00 - 15:30, 2026-09-16 19:30 - 2026-09-17 21:00, 2026-09-17 19:30 - 2026-09-18 21:00, 2026-09-18 19:30 - 2026-09-19 21:00 | Gloucester Stage Company, East Main Street 267, Gloucester, M, 01930, United States
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 as we discover how our pasts shape, protect, and connect us all in this time-bending, regional premiere drama.
Written by Pulitzer Prize winning playwright James Ijames and directed by Dawn M. Simmonsº, Moon Man Walk runs September 13 to 29. All performances are at the Natti-Willsky Performance Center – 267 East Main Street, Gloucester. Showtimes are Wednesdays – Saturdays at 7:30pm, with matinees Saturdays & Sunday at 2:00pm.

A Band of Brothers - More than just and Allman Brothers Tribute
2026-09-11 20:00 - 22:00 | The Cut, 177 Main Street , Gloucester, MA, 01930, United States
18+, Positive I.D. Required
“A Band Of Brothers” isn’t just an Allman Brothers tribute band; they’re a powerhouse, uniting the top-tier talent of the East Coast. The brainchild of ace Boston guitarists Ryan Taylor and Johnny Trama, this collective, more than a mere homage, harness the Allman Brothers tradition as a vehicle to bring a unique and exciting experience every night. The ensemble features artists from an array of bands including – North Mississippi Allstars ,Dickey Betts and Great Southern, Pink Talking Fish, Neighbor, Dub Apocalypse, Peter Wolf’s Midnight Travelers, Dickey Betts Great Southern, Slightly Stoopid, Sonya Rae Taylor, Band of Killers and more.
Matt Zeiner began his professional music career touring with Matt “Guitar” Murphy, who exposed him to a fusion of blues and jazz. His career took a significant turn in 2000 when Dickey Betts of the Allman Brothers Band recruited him as a keyboardist and vocalist, leading to a fruitful collaboration and tour.
Ryan Taylor on slide guitar spearheads the band with his exceptional talents. His journey, steeped in the rich musical traditions of Austin and Nashville, saw Ryan honing his craft the old-fashioned way.
Johnny Trama on guitar conjures up riffs and rhythms that speak volumes. His journey through the realms of rock, soul, and blues, playing with icons like Bettye LaVette and Jesse Dee, has armed him with a mystical musical prowess.
Jesse Williams on bass is an alchemist of groove, spinning each note into a rhythmic tapestry. His Grammy-nominated escapades with the likes of Duke Robillard and Joe Louis Walker have endowed him with a bass prowess that’s both fluid and formidable.
Tom Arey behind the drums is nothing short of a powerhouse, orchestrating beats and fills with the finesse of a seasoned composer. His tenure with Peter Wolf’s Midnight Travelers has honed a style that’s explosive yet eloquent, much like the Allmans’ own percussive legends.
Brendan Tommaney on percussion is a true artist, painting rhythms with a palette of beats and textures. Educated at the New England Conservatory of Music and seasoned with groups like Pink Talking Fish, Tommaney brings a jazz-infused sensibility that adds depth and dimension to the band’s sound.
Paul Wolstencroft on keyboards crafts melodies that mesmerize and transport. His tenure with Slightly Stoopid has given him a swagger that shines through each performance, weaving a spell of harmonies and counter-melodies that elevate the band’s tribute from mere replication to a reimagined homage.

Our Founding Mothers and Fathers: More Revolutionary War Connections to the Salem Witch Trials
2026-09-17 13:00 - 14:00 | virtual program
Each year we meet hundreds, if not thousands, of individuals who can trace their family line back to the Salem witch trials. We often tell visitors that the English colonists of 1692 were the founding fathers and mothers of our country. They were themselves descended from the earliest settlers, who were establishing a new country and took the biblical instruction “be fruitful and multiply” to heart.
It is fascinating to consider the many connections between the Salem witch trials and the Revolutionary War generation, particularly the one most often referred to as our “Founding Fathers.” Part II of our Rev250 lecture series will focus on four more notable connections, including witchcraft skeptic Robert Calef, Ipswich court clerk Thomas Wade, condemned witch Mary Bradbury, and accuser Bathsheba Pope.
Join us on Thursday, September 17th at 1:00 pm for this free, virtual program.
Registration is required for this event.

Tanya Donelly
2026-09-17 20:00 - 22:00 | The Cut, 177 Main Street , Gloucester, MA, 01930, United States
Tanya Donelly first emerged in the indie-rock landscape in the early 1980s, co-founding Throwing Muses (with stepsister Kristin Hersh), then later co-forming The Breeders, before leading her own band Belly in the 1990s. With Belly she had her biggest commercial breakthrough, notably with the single “Feed the Tree”, earning critical acclaim and a Grammy nomination.
After that success, Tanya embarked on a solo career marked by lyrical richness, melodic innovation, and a shifting musical palette that embraces folk, country, ambient, and indie pop textures. Her solo debut, Lovesongs for Underdogs (1997), established her distinct songwriting voice outside of her band projects.
This Hungry Life (originally released in 2006) is a live album recorded in a unique intimate setting — a closed hotel in Bellows Falls, Vermont — featuring largely new material, plus a few covers and re-imagined tracks. The album reflects maturity in both voice and subject matter: themes of home, family, identity, and the passage of time are woven through in her warm vocals and intimate performance style, with the live setting giving the songs immediacy and connection.
Marking the 20th anniversary of This Hungry Life offers a chance to revisit her work at this pivotal moment: affirming her legacy in indie rock; celebrating her evolution as an artist who has never stopped refining her craft; and presenting This Hungry Life not just as a document of a live show but as a milestone in her ongoing journey — both musically and personally.
The Guardian:
“Recorded live in a disused Vermont hotel, Donelly’s vocal, full of personality, soars brightly over the audience and fills you with affection for hearth and for home.” The Guardian
