Even though the theme this year is “Your Favorite Children’s Book”, you can make anything for your entry.
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Middle Street Walk: Events at Sawyer Free Library
Middle Street Walk
Saturday, December 13 | 10:00 AM–4:00 PM
Sawyer Free Library · 2 Dale Avenue, Gloucester, MA
Celebrate the 27th annual Middle Street Walk, a beloved Gloucester holiday tradition where “the past is present!” Enjoy a festive day filled with music, art, community events, and FREE horse-drawn wagon rides along historic Middle Street. The Sawyer Free Library is excited to be part of the celebration with special programs for all ages.
Festivities at the Sawyer Free Library
10:30–11:30 AM — Holiday Music & Card Making for Kids
Drop in for cheerful music and hands-on card-making fun — perfect for children and families.
12:00–2:00 PM — Walker Creek Saxophone Quartet Performance
Enjoy a live performance from this talented saxophone quartet, filling the Library with seasonal favorites and jazzy flair.
1:00–4:00 PM — Tours of the Saunders House Historic WPA Murals
Professional conservator Lisa Mehlin will lead 15-minute guided tours of the newly restored WPA murals in the historic Saunders House. Learn about their remarkable history and the intricate conservation process. Registration required at SawyerFreeLibrary.org.
1:00–1:30 PM — Gingerbread Creation Contest Winner Announcement
Join members of the Middle Street Walk Committee — including Barbara Catalini of Cakes by Barbara — in the Children’s Room as they announce the winners of the 2025 Gingerbread Creation Contest. All gingerbread entries will be on display!
More details on Middle Street Walk festivities city-wide will be shared soon. We hope you’ll join us for this magical Gloucester tradition!
10 DAYS TO THE 2025 MIDDLE STREET WALK The program of the day’s events are listed on www.middlestreetwalk.org and paper programs will soon be available at shops and organizations around town. The rules for the Gingerbread Creation Contest are also listed there. There’s still time to make an entry! So much Free Fun to start the holidays!
Gloucester residents are welcomed for FREE EVERY TUESDAY at the Hammond Castle Museum. Nearly a dozen Christmas trees, dozens of wreaths, garlands and hand-made bows, two Menorahs, and playful 3D printed touches including gumdrop garland and a replica of the castle styled as a whimsical gingerbread house fill the space. Thousands of twinkling lights and flickering candles set the scene while nutcrackers, gingerbread men, and hidden gnomes and elves add a bit of fun for little ones exploring with their families.
Over the last several seasons, we have grown this program, and that tradition of care has long been guided by our Director of Collections, Beth Welin, whose thoughtful eye has shaped its beauty from the start. This year we were also fortunate to have the generous support of Elaine Quinn, of Elaine Quinn Interiors whose time, encouragement, and friendship helped us elevate the experience for the 2025 season.
We invite you to join us and experience the beauty and joy of the season. Proof of Gloucester residency is required at check-in for all those with Gratis Day admission reservations.
– Gloucester Gratis Days Self-Guided Tours are available every Tuesday throughout the entire 2025 tour season from May 6th through January 4th.
– Advance registration is recommended but not required. You may also register upon arrival in the Museum Shop.
Rockport Holiday Shopping Night
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!
Local Favorite Chelsea Berry Returns to the Great Hall For Two Performances This December!
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.
Reserve your tickets at: https://bit.ly/ChelseaHCM
A CELTIC CHRISTMAS:DASHING ROCK TRIO December 6th at 7:30pm
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 Rock Trio 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.
Sawyer Free Library to Host Film Screening and Panel Discussion: “Timeline Cape Ann: Sawyer Free Library”
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 of 1623 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.
Space is limited; registration is requested at SawyerFreeLibrary.org.
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
Backyard Growcery December Pop-Up Market
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.
Backyard Growers FUNdraiser: Holiday Door Swag Workshop
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.
Cape Ann Community 