Halloween lands on a Saturday in 2026, so you might expect Charlestown's ticketed, scheduled and promoted events to pile up on October 31. They pile up on October 24 instead. This Saturday and Sunday, October 24 and 25, hold the dog parade, The Anchor's family trick-or-treat, a pop-up market, an evening fire show in the Navy Yard and Halloween in the Gardens. On the actual holiday, the Navy Yard's busiest event venue has nothing on its calendar.
That split shapes both weekends. The weekend of October 24 is the planned one, and it has a scheduling conflict to sort out. October 31 runs on stoops, porch candy and a neighborhood tradition with no ticket page.
Saturday, October 24, and the 11 o'clock problem
Two of the weekend's biggest family events start at the same hour, about a mile apart.
The Charlestown Patriot-Bridge reports that the CharlestownDogs community group is bringing back its annual Howl-O-Ween Dog Costume Parade to the Charlestown Training Field from 11 a.m. to 1 p.m. It's free, with prizes for the best costumes. If the weather turns, the rain date is Sunday, October 25. The group posts updates on Instagram at @charlestowndogs, so check there Saturday morning if the sky looks uncertain.
The same two hours, 11 a.m. to 1 p.m., belong to The Anchor's Family Trick-or-Treat at 1 Shipyard Park in the Navy Yard. It has trick-or-treat stops, photo ops, pumpkin decorating and live music, and The Anchor's partners, vendors, friends and staff all take part.
A household with a costumed dog and a costumed kid has a choice to make. Here's how the day lays out:
- 11 a.m. to 1 p.m. Howl-O-Ween Dog Costume Parade at the Training Field, and Family Trick-or-Treat at The Anchor.
- 11 a.m. to 4 p.m. Halloween Pop Up Market at The Anchor.
- 1 p.m. to 4 p.m. Bunker Hill Monument open for climbs, with the last climb 30 minutes before closing.
- 6 p.m. to 11 p.m. Nightmare in the Navy Yard: Fall Fire Fest Edition at The Anchor.
The market's long window is what makes both midday events possible. Do the parade first, walk down to the waterfront and you still have the afternoon at the market. The Monument fits in too. The National Park Service's off-season hours for the Bunker Hill Monument began October 13 and run Wednesday through Saturday, 1 to 4 p.m. Your last chance to climb on the 24th is 3:30.
Afternoon and evening belong to the Navy Yard
The Halloween Pop Up Market at The Anchor runs Saturday from 11 a.m. to 4 p.m., with free admission. Food and drinks are for sale. One listing's write-up talks about spending "a Sunday afternoon" there. Ignore that line. The date fields on The Boston Calendar and Eventbrite both say Saturday, October 24. Expect local artists, makers and small businesses selling art and handmade goods, plus The Anchor's urban pumpkin patch and Halloween decorations. Costumes are encouraged.
The Anchor's homepage says the pumpkin patch is currently open for fall but doesn't give a closing date. If you want pumpkin photos, the 24th is a safe day to get them. Waiting for the 31st is a gamble.
After dark, The Anchor turns into something else. Nightmare in the Navy Yard: Fall Fire Fest Edition runs from 6 to 11 p.m. with live fire performances, cirque acts, haunted attractions, a movie lounge, costume contests, desserts and seasonal food and drink. General admission is free. VIP options are $95 per couple or $325 for a group of up to four.
All in, The Anchor fills the 24th from 11 in the morning to 11 at night, with three separate Halloween events in one day at one address. That's where the concentration comes from. The venue that runs the most Halloween programming in Charlestown has put it all on the Saturday before the holiday.
Sunday morning on Main Street
The weekend wraps up uphill. On Sunday, October 25, Gardens for Charlestown holds Halloween in the Gardens at 499 Main Street from 10:30 a.m. to 1 p.m. The lineup includes arts and crafts, face painting, balloon twisters, Knucklebones games and pony rides.
Admission is $10 per child, and some activities cost extra. The $20 advance bundle covers admission, a pony ride, face painting, a hot dog and a drink. Pony rides run only from 10:30 to 12:30 and stop half an hour before the event ends, so arrive early if they're the main draw. You can also buy tickets at the Gardens that morning.
Sunday is also the dog parade's rain date. If Saturday gets washed out, the parade and the Gardens event will overlap on Sunday morning instead.
October 31: the venue calendar goes quiet
Here's the other half of the split. The Anchor's public calendar shows "No events" for Saturday, October 31. On Charlestown's actual Halloween, the neighborhood's biggest event venue is out of the picture.
What fills the day is smaller, earlier and mostly run by neighbors.
The morning starts with a workout. According to Caught in Charlestown, Flight House Fitness and Battista Boot Camp are teaming up for a Halloween Boo-Camp, with classes at 8 and 9:30 a.m., plus recovery, vendors and a DJ. It's free for members and $25 for non-members, and 100% of proceeds go to the Boys & Girls Club of Charlestown. Flight House Charlestown is at 465 Medford Street, Suite 1000.
During the day, the streets become the show. Caught in Charlestown is running a Halloween Decorating Contest. Entry costs $20, and entrants get a small yard sign with a QR code that passersby scan to vote. Entry fees support Harvest on Vine, Charlestown's food pantry. First, second and third place each win a gift card to Prima, Waverly or Monument, the winner's choice. The same post notes that people from all over the city cross the bridge to walk Charlestown's decorated streets. The contest post doesn't give a judging date. Still, signs that go up before the 24th will be seen by both weekends' crowds.
The Monument keeps its usual Saturday hours on the 31st, 1 to 4 p.m. It closes right before the neighborhood's biggest Halloween hour begins.
For dinner after trick-or-treating, Caught in Charlestown also reports that the City of Boston has extended its 2026 outdoor dining season through November 15, weather permitting. The city keeps an outdoor dining map of participating restaurants. A Saturday Halloween with patios still open is a rare combination.
Monument Square, on its own terms
The evening has belonged to the Monument Square Halloween Trick-or-Treat for four decades. Last year's edition, as the Patriot-Bridge reported in 2025, was the 40th. It started at 5 p.m. on the Bunker Hill Monument steps at the top of Monument Avenue, and the founders came back to mark the milestone. The theme was "Bunker Hill 250th – American Revolution."
The 2025 announcement said everyone is welcome, with the focus on the children, and described the evening this way:
"The event remains a neighbor-to-neighbor celebration, not promoted outside Charlestown, to preserve its close-knit, community feel."
In 2025, organizers asked residents around Monument Square, the Training Field and Monument Avenue to decorate and to stock extra candy, since those homes are popular stops and often run out. They also invited trick-or-treaters to bring canned goods, cereal and other non-perishables for Harvest on Vine.
Organizers had not posted a 2026 time, theme or meeting point as of mid-October. The 5 p.m. start at the Monument steps is how 2025 worked. For this year, watch the Patriot-Bridge and neighborhood channels rather than assuming last year's schedule. And if your home is near the Square, the 2025 advice to stock extra candy is easy to follow either way.
Whether you're decorating a stoop on Monument Square or planning a dog costume for the Training Field, the Tracy Shea Real Estate Team keeps close track of Charlestown's calendar all year, from parade mornings to Monument hours. If you'd like to talk about life in the neighborhood, or a home in it, we'd be happy to help. Schedule a Consultation.
