Rally the corgi has sniffed out the Christmas events for kids in Gloucester for 2026. Hammond Castle Museum fills every room with nutcrackers, elves and candlelight for Deck the Halls through January 3, and Santa trades his sleigh for a ship on Beauport Cruiselines’ Santa at Sea sailings on Sunday, December 13. We check every date on the host’s own website or the official Cape Ann tourism calendar and link straight there. For the rest of the state, see our Massachusetts Christmas events for kids guide.
What Rally found in Gloucester
- 2 Christmas events for kids in Gloucester
- Deck the Halls: Hammond Castle Museum, daily 9 am to 3:30 pm through January 3
- Santa at Sea: Sunday, December 13, three sailings, $35
- Sensory-friendly 11 am sail and a PJ sail at 5 pm
- Every date checked on the Cape Ann Chamber calendar on Nov 11
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Ticketed and paid Christmas events for kids in Gloucester
Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.
Event hosts: free events are listed first. The #1 spot puts your event at the top of this page.Inquire about the #1 spotAdd your event for free
Castle holiday display
Deck the Halls at Hammond Castle Museum
- When: Daily, November 20, 2026 to January 3, 2027, 9 am to 3:30 pm; closed Thanksgiving, Christmas Eve, Christmas Day, New Year’s Eve and New Year’s Day
- Where: Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930 (opens in maps)
- Cost: Museum admission; pricing varies, see the museum’s website
- Ages: All ages
Expand to see the parent tip
Hammond Castle Museum on Gloucester’s waterfront dresses every room for its 8th annual Deck the Halls, a museum-wide holiday installation lit with candlelight and fairy lights.
Kids can hunt for the royal guard of nutcrackers, a gingerbread replica of the castle, and the elves and gnomes hidden around the rooms, while two menorahs mark Hanukkah alongside the Christmas trees.
Parent tip: Give younger kids a mission, like counting nutcrackers or spotting every gnome, to keep them engaged through the castle’s many rooms.
- Host
- Hammond Castle Museum (opens in a new tab)
- Address
- Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930 (opens in maps)
- Confirmed
- On the host’s page, checked
New Gloucester events every week
Rally researches Christmas events in Gloucester daily and updates this page with new events. Enter your email to get a weekly update with new events in Gloucester.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
Rally’s Christmas research
Rally the corgi has 1 more Gloucester event researched for you.
- New events every week We research new events daily and send you one email a week with the new ones we find in Gloucester.
- Exclusive access to free events Find the free Christmas events in Gloucester before they fill up.
- Unlock the filters Find Santa visits, free events and weekend plans in one tap.
- Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
- One-tap add to calendar Save any event to your Google, Apple or Outlook calendar so you never miss it.
Coming up on this page
- 1 Santa
- 1 Lights
Enter your email to get new Christmas events in Gloucester every week.
Santa cruise
Santa at Sea Cruise
- When: Sunday, December 13, 2026, sailings at 11 am, 2 pm and 5 pm (90 minutes each)
- Where: Beauport Cruiselines, Rowe Square, 6 Rowe Square, Gloucester, MA 01930 (opens in maps)
- Cost: $35
- Ages: Families with kids
Expand to see the parent tip
Beauport Cruiselines takes Santa out on Gloucester Harbor for three family sailings, each with photos with Santa, festive games, hot cocoa and cookies.
The 11 am sail is sensory-friendly with no loud music, the 2 pm sail is the classic version with holiday tunes, and the 5 pm Holly Jolly PJ Sail brings pajamas, waterfront lights and a reading of The Polar Express.
Parent tip: Bring a new, unwrapped toy for the Cape Ann Kids Holiday Fund, and pick the 11 am sail if your child does better without crowds and loud music.
- Host
- Beauport Cruiselines (opens in a new tab)
- Address
- Beauport Cruiselines, Rowe Square, 6 Rowe Square, Gloucester, MA 01930 (opens in maps)
- Confirmed
- On the host’s page, checked
New Gloucester events every week
Rally researches Christmas events in Gloucester daily and updates this page with new events. Enter your email to get a weekly update with new events in Gloucester.
Free. Unsubscribe anytime. Privacy policy (opens in a new tab)
We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Massachusetts Christmas train rides page.
See every event on a December calendar
Plan your December
When each Gloucester Christmas event for kids happens
Visit Hammond Castle on any day that suits you before the new year, and book one of the three Santa at Sea sailings on December 13 early.
- Deck the Halls at Hammond Castle MuseumGloucester · Nov 20 to Jan 3
- Santa at Sea CruiseGloucester · Dec 13
Looking further afield? Our Massachusetts Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Haverhill, Andover, Gloucester and Boston. The national search sorts every event by distance from your town.
A story for the drive home
A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.
A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.
Buy on AmazonKeep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Massachusetts city.
Gloucester Christmas events for kids: questions parents ask
What are the best Christmas events for kids in Gloucester this year?
Rally Takes the Train has confirmed 2 Christmas events for kids in Gloucester for 2026: Deck the Halls at Hammond Castle Museum, running through January 3, and Beauport Cruiselines’ Santa at Sea cruises on December 13.
When is Deck the Halls at Hammond Castle in 2026?
Daily from November 20, 2026, through January 3, 2027, from 9 am to 3:30 pm. The museum is closed Thanksgiving, Christmas Eve, Christmas Day, New Year’s Eve and New Year’s Day.
When is the Santa at Sea cruise in Gloucester?
Sunday, December 13, 2026, with sailings from 11 am to 12:30 pm, 2 to 3:30 pm and 5 to 6:30 pm from 6 Rowe Square. Tickets are $35.
Is there a sensory-friendly Santa event in Gloucester?
Yes. The 11 am Santa at Sea sailing on December 13 is a calm, sensory-friendly cruise without loud music or a DJ.
Who do I contact about Gloucester holiday events?
Hammond Castle Museum at info@hammondcastle.org, and Beauport Cruiselines at BeauportCruiselines@CruiseportGloucester.com.
Are there Christmas train rides for kids in Massachusetts?
Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Massachusetts Christmas train rides page.
How do you confirm these events?
We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked Gloucester on November 11, 2026. Rally is also contacting each organizer to confirm details like parking, restrooms and bad-weather plans.
Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.