Kick off the season in festive Rockport style! Join us for Holiday Shopping Night and enjoy an evening of cheerful lights, local treasures, and holiday spirit. Start at Dock Square, where shoppers can pick up a free Christmas in Rockport tote bag filled with a list of participating businesses, special coupons valid all season long, and a bonus raffle ticket. As you explore Rockport’s charming shops, you’ll find festive treats and refreshments offered by many local retailers and be serenaded by strolling musicians bringing holiday magic to the streets. Every purchase at a participating store earns you an extra raffle ticket for a chance to win one of three exciting prizes. End the evening at the after party and live raffle drawing at Brackett’s Oceanview Restaurant where the celebration continues with good company, great prizes, and plenty of holiday cheer!
Cape Ann favorite and acclaimed singer-songwriter Chelsea Berry returns to the Great Hall at Hammond Castle Museum for two special holiday performances, accompanied by Kristen Miller on cello. Known for her soulful voice and heartfelt songwriting, Chelsea will perform selections from her holiday album Ring the Bells, along with songs that celebrate joy and togetherness.
On Saturday, December 6, (Doors at 6:30 pm | Performance at 7:00 pm), guests have two ticket options. Those with VIP Tickets arrive at 6:00 pm for an intimate Meet & Greet with Chelsea, including a complimentary champagne toast and preferred seating. Capacity is limited for this exclusive experience. General Admission ticket holders are welcome to arrive for the 7:00 pm performance.
On Sunday, December 7, (Doors at 5:00 pm | Performance at 5:30 pm), families are invited to join in festive sing-alongs, creating a fun and memorable night for all ages.
Chelsea has deep roots on the North Shore and Cape Ann, with past sold-out performances at some of the region’s most beloved venues. Her 2019 concerts at Hammond Castle Museum remain among our most memorable evenings. Over a 25-year career spanning twelve albums, she has toured coast to coast, sharing stages with legendary artists including Mavis Staples, Livingston Taylor, Chris Isaak, and Shawn Colvin.
As Thanksgiving approaches, we know that the holiday season is nearly here, so it’s time to start marking your calendars with December concerts and gatherings.
The Gloucester Meetinghouse Foundation is pleased to present the Dashing Rock Trio in a Celtic Christmas Concert with timeless melodies reimagined, on Saturday December 6th at 7:30pm in the Gloucester Unitarian Universalist Church, at the corner of Middle and Church Streets.
Based on the isle of Nahant in Boston Harbor, Dashing Rock Trio explores the music of the Celtic nations and beyond with varied instrumentation, including fiddle, nyckelharpa, flute, whistle, guitar, accordion, Scottish smallpipes and voice.
Elizabeth Ketudat, Dave Cabral, and Sarah MacConduibh have performed together for decades in multiple ensembles. They bring their deep friendship and experience to create the ensemble’s unique sound, a blend of tradition and fresh interpretation.
Dashing RockTrio performs at festivals, concerts, and private events. Whether on a grand stage or a cozy local venue, they bring vibrant energy and musicianship to every performance. We are delighted to present them to the community in the fine acoustics of our historic 1806 Meetinghouse.
Tickets are available at the door and online (recommended) with more information on our website. General admission is $30, students $10, under age 12 free.
Parking is available on the Green, entered between the granite pillars at 50 Middle Street, and around the Historic District. The side entrance at 10 Church Street offers elevator access.
Ever wonder how Gloucester’s public library came to be? The Sawyer Free Library invites the community to a special evening celebrating nearly two centuries of local history, innovation, and civic spirit. On Thursday, November 20 from 5:00 to 6:30 PM, the Library will present a film screening and panel discussion of Timeline Cape Ann: Sawyer Free Library in its Community Room.
Produced by Kory Curcuru of1623 Studios, Timeline Cape Ann: Sawyer Free Library traces the remarkable story of Gloucester’s public library—from its 19th-century beginnings in the Gloucester Lyceum to its role today as a vibrant civic and cultural hub. The short documentary explores how a small-town vision grew into a cornerstone of learning, access, and community connection.
The film situates the Sawyer Free Library within the broader story of American public libraries—beginning with Benjamin Franklin’s 1731 subscription library, which sparked a movement for shared knowledge and free access to books. By the early 1800s, the “Lyceum movement” swept New England, bringing citizens together for lectures, debate, and education. Gloucester quickly joined in. In 1830, residents established the Gloucester Lyceum, which merged Franklin’s ideals with this new spirit of civic learning.
The Library’s evolution accelerated under the leadership and generosity of Samuel Elwell Sawyer, a Gloucester native and philanthropist who made access to books free for all. His lasting legacy includes the donation of the Saunders House, which remains part of the Library campus today, and the 1872 incorporation of the Gloucester Lyceum and Sawyer Free Library, with a charter promising it would remain free forever.
Timeline Cape Ann also highlights the Library’s continued resilience and innovation—surviving fires, embracing technology, and expanding services through the 20th and 21st centuries. From WPA murals and children’s programs to its newly completed, state-of-the-art renovation and expansion, the Sawyer Free Library remains a living institution shaped by generations of readers, learners, and citizens.
Following the screening, Curcuru will be joined by Sawyer Free Library Local History Librarian Julie Travers and local historian and author Wayne Soini for a panel discussion and audience Q&A exploring the Library’s enduring role in Gloucester’s civic life.
This free public event offers a fascinating look at how one man’s generosity and a community’s shared commitment helped shape the heart of Gloucester.
Film Screening and Panel Discussion: Thursday, November 20, 2025 5:00–6:30 PM Sawyer Free Library, Community Room (Ground Floor), 2 Dale Avenue, Gloucester, MA
Gloucester’s weekly farmers market The Backyard Growcery is BACK for a pop-up holiday market hosted at The Cut in downtown Gloucester on Saturday, December 6, 12-3pm. Brought to you by Backyard Growers, stop by to celebrate the season in community, shop farm-fresh and locally-made foods, enjoy live music, and more, all in a great location. SNAP accepted. Plus, the Growcery is offering a $20 SNAP match per SNAP customer, through Backyard Growers’ Market Mint program.
Featuring:
Farm-Fresh & Locally-Made Food
Community Seed Swap
Eco-friendly Gifts for the Gardener
Family Holiday Craft Corner
2026 Backyard Growers Garden Applications
Live Music
And More!
Backyard Growers is a 501(C)3 nonprofit organization committed to creating equitable access to the resources, space & knowledge people need to grow their own food in our community and 100% of Gloucester Public Schools. Learn more about Backyard Growers at backyardgrowers.org.
Join Backyard Growers for an evening of festive fun for a cause at our FUNdraiser: Holiday Door Swag Workshop! Learn to make your own holiday swag for your door using seasonal foraged materials found on Cape Ann. We’ll provide drinks, nibbles, and all the materials.
Proceeds support Backyard Growers’ work creating equitable access to the resources people need to grow their own food in our community and at 100% of Gloucester Public Schools.
Tickets are selling very quickly.Don’t miss your chance to step back in time without going up the line.
Rain or Shine!
Step into the world of medieval and Renaissance culture at Hammond Castle Museum, where the castle itself provides a uniquely dramatic backdrop for a magical day steeped in history and fantasy in a stunning setting.
Experience the excitement of The Brotherhood of the Arrow and Sword as they return with their high-energy armored combat demonstrations, bringing the medieval battlefield vividly to life. Enjoy captivating performances from the L.I.A.R.s, who will fill the air with sea shanties, alongside a hulahoop artist, a storyteller, a wandering harpist, a bubble faery, and other enchanting entertainers. New this season, our kids’ tent offers little princes and princesses a craft for hands-on fun. With more vendors and food trucks than before, this year’s Faire is bigger, better, and more magical.
We are thrilled to host James B. Jones and Shelley Wolfe of Netflix’s Emmy Award-winning Love on the Spectrum (LOTS) will be joining us as our Honorary King and Queen! (You may remember that James was featured on a date at the Museum in Season Two, Episode 5 of LOTS! You can read more about that date here!) James and Shelley will be strolling the Museum grounds in full Renaissance spirit, and guests will have the opportunity to meet them and take photos with them from 11:00 am – 2:00 pm.
Your admission includes access to explore parts of the interior of the Museum and free access to all scheduled entertainment. *Vendor services are not included, and cash is recommended due to limited wi-fi. Cosplay is encouraged, but weapons of any kind are not permitted. Little ones ages 4 and under are free but do require a reserved ticket, and kids ages 5 – 12 are only $10! Hammond Castle Museum Member savings apply.
Don’t miss this extraordinary day of music, pageantry, and living history at Hammond Castle Museum, where the past comes alive in spectacular fashion!
Off-Site Parking is Required & Free Shuttles will run all day: Free parking will be available at Stage Fort Park (24 Hough Ave, Gloucester, MA 01930), with complimentary white Beauport shuttles, generously sponsored by Townsend Energy, running between the park and the Museum from 8:45 AM to 5:15 PM. On-street parking on Hesperus Avenue is prohibited. On-site parking is reserved exclusively for guests with mobility needs and is not guaranteed.
Cold Chocolate, a Boston-based duo that calls itself “a genre-bending Americana band,” makes its Cape Ann debut on Saturday, Nov. 15, at 7:30 p.m., as part of the Gloucester Meetinghouse Foundation’s 10th Anniversary series of concerts, lectures, silent movies and more. The location is the landmark 1806 Meetinghouse that is Gloucester’s oldest standing church and the home of the Gloucester Unitarian Universalist Church.
With Ethan Robbins on vocals, guitar and mandolin and Ariel Bernstein on vocals, percussion and banjo, Cold Chocolate fuses folk, funk and bluegrass and has released five albums. Simon Waxman of The Boston Review wrote that Cold Chocolate’s high energy and original music “sounds softer than the dew on the mountainside, harder than a Harley pushing back red dust, and sweeter than true love.”
With music for all ages, the band has shared bills with Leftover Salmon, David Grisman and Angelique Kidjo, and performed at festivals across the country. Tickets are available at the door and online with more information at: www.gloucestermeetinghouse.org. General admission is $30, students $10, under age 12 free.
The Gloucester Unitarian Universalist Church is located at 50 Middle Street in Gloucester. Parking is available on the Green in front of the Meetinghouse and at other locations in the Historic District. The side entrance at 10 Church Street offers elevator access.
The Gloucester Unitarian Universalist Church started its history as the first Universalist church in America in 1779, a rebellious congregation that played an important role in the quest for religious freedom as enshrined in the First Amendment to the United States Constitution. The architecturally significant building predates lighthouses on Cape Ann and is on the National Register of Historic Places. The Gloucester Meetinghouse Foundation is an independent, secular nonprofit 501(c)(3) corporation dedicated to the historic building’s preservation and its use for and by the Cape Ann community.
The Gloucester Rotary has published a 12-month Cape Ann photo calendar for 2026, featuring the photography of several local photographers. In addition to the beautiful photography, each calendar includes a raffle ticket for a $50 weekly raffle drawing throughout the year. The calendars are $25 each and proceeds from sales will be used for the Gloucester Rotary’s many community and international activities. Calendars may be purchased online at BankGloucester (160 Main St, Gloucester), the Weathervane (153 Main St, Gloucester), and at the Greater Cape Ann Chamber of Commerce (24 Harbor Loop, Gloucester) or from any Gloucester Rotarian.
Join 
Proceeds support Backyard Growers’ work creating equitable access to the resources people need to grow their own food in our community and at 100% of Gloucester Public Schools.
Cape Ann Community 