I believe every kid who has ever trick-or-treated knows of one house on each block you dare not tread. My neighborhood was no different. Halloween was a Top 3 event on every kid’s social calendar, and for me, it was numero uno. All Hallows Eve was the holiday equivalent of my Super Bowl, and trick-or-treat candy was my Lombardi Trophy. Each year, I suited up, grabbed my pillowcase, and hit the street in search of candy like I was storming the field.
On this particular Halloween, I was 12 and disguised as Freddy Krueger for the second consecutive year. It had rained earlier, so by 6 p.m., the air was crisp, and the streets reflected the sky, adorned with fallen orange and brown leaves. My crew included my brother, two cousins, and four friends, united on a mission for every Snickers bar and Twix within an eight-block radius.
Most houses were the same—“Great costumes!” followed by a few chocolates tossed into our bags. But then we spotted an old Victorian house that had been abandoned for years, its lights now glowing. We exchanged nervous glances, knowing this was a bad idea, but the mission was the mission
We marched up the stone walkway, our hearts racing. Three large oak trees loomed in the yard, and dim lighting flickered from a second-floor window.
“TRICK OR TREAT!!!” we yelled. The door swung open to reveal a man in his early 30s, looking like Weezer’s lead singer. “You guys want some candy?” he asked, gesturing us inside. Wait, that’s not how this works!
He led us into a dimly lit kitchen filled with bowls of full-size candy bars. “Help yourself, kids!” As we dove into the unexpected stash, I noticed a group of people sitting on the floor in a candlelit room nearby—no furniture, just smiles. One waved at me, and before I could react, the man said, “And you guys are welcome over any time.” My friend Charles immediately bolted for the door, exclaiming, “F THAT SHIT!”
After a few more handfuls of candy, I grabbed my brother, and we fled, laughing all the way home with the greatest candy haul of our lives. What became of Rivers and his odd crew remains a mystery. We never saw them again, not even in the neighborhood. That house? We stayed far away. They were probably vampires.
Mrs. Ambrose drew her arm within her husband’s, and as they moved off it could be seen from the way in which her sloping cheek turned up to his that she had something private to communicate.
In the years since, I’ve learned that some of the best neighborhoods for trick-or-treating in Boston — where the only thing haunting the streets are kids and their candy bags!
- Beacon Hill: Known for its historic charm, the streets around Louisburg Square are especially friendly, with many residents eager to hand out treats.
- Back Bay: The streets along Commonwealth Avenue and Marlborough Street are lined with beautifully decorated homes and a mix of traditional and gourmet candy options.
- West Roxbury: The neighborhoods around the West Roxbury Village and around the parks are great for families, with plenty of houses ready to welcome trick-or-treaters.
- South End: Check out the area around Tremont Street and Washington Street, where residents often go all out with decorations and creative treats.
- Jamaica Plain: The streets around Centre Street and the Arborway are popular, with many families participating in a lively Halloween spirit and community events.
- Charlestown: The area near Bunker Hill and along Main Street features a tight-knit community with lots of candy and decorations, making it a fun spot for kids.
- North End: While it’s famous for its Italian restaurants, neighborhoods like Hanover Street and Salem Street see residents sharing treats, making it a unique trick-or-treating experience.
- Dorchester: Areas around Adams Village and Neponset feature friendly neighbors and lots of activities, perfect for a festive Halloween night.