Fall in New England is the perfect time to get out and about with family or friends—and what better occasion to celebrate the season than Halloween? Boston has plenty to offer when it comes to reasons to dress up in costume and explore the city during this festive time of year.
From trick-or-treating in one of Boston’s decked out neighborhoods or participating in a dog costume parade, to going all out at the Haunted Happenings in Salem or running a 5K in costume, you won’t be disappointed in this list of activities and events to check out. And also keep in mind that most of the city’s top restaurants and bars offer Halloween-inspired specials and events, so no matter where you plan on heading, be sure to pack a costume for your Halloween trip to Boston!
Check Out Salem's Haunted Happenings Activities Throughout October
While the annual Salem Haunted Happenings takes place in a Boston suburb, this is where you’ll want to be if you’re looking for a fully immersive Halloween experience during October. Each year, over 250,000 people visit Salem to celebrate, with 2019 being the 37th year. Why Salem? This historic town is home to the Salem Witch Trials of 1692. And you can get to Salem from Boston on the MBTA Commuter Rail or Ferry.
Take a Ghosts and Gravestones Tour
Go “from Beantown to Screamtown” on the Ghosts and Gravestones Tour aboard the Trolley of Terror, where you’ll learn all about the city’s ghost stories. The tours do run throughout the year—daily from April to October; Saturdays from December to March—but Halloween is the perfect time to take one. This 90-minute tour will take you to sites like the Omni Parker House, a haunted hotel and a 400-year-old unmarked burial ground, while listening to stories about gruesome executions, grave-robbing, punishments and more that took place throughout Boston’s history.
Go Trick-or-Treating in One or More Boston Neighborhoods
Of course, a prominent Halloween activity, but going trick-or-treating in one of Boston’s neighborhoods is a great way to experience the city during this festive time of year. Many of the historic and picturesque areas like Beacon Hill, the Back Bay, and Charlestown deck out their brownstone-filled neighborhoods with seasonal displays and décor that adds to the experience. Depending on where you’ll be, be sure to check ahead on the neighborhood’s website or social media pages, as dates and times for trick-or-treating can vary. Good news: that means the kiddos can dress up and collect candy on more than one night!
Get Your Shopping in While the Kids Trick-or-Treat at the Prudential Center's Pru Boo
For 25 years, the Prudential Center has been hosting its Pru Boo event, where families can trick-or-treat in the popular shopping plaza indoors amongst more than 50 participating stores and restaurants the Sunday before Halloween. Aside from filling the little ones’ bags with candy and parading around in costumes, families can enjoy activities including face painting, magic shows, and even a kids’ concert, the latter of which is weather permitting given that it’s held in the South Garden outdoors.
To participate, show up and give a $5 donation to local nonprofit Playworks or do so online in advance. Parking at the Prudential Center is $18, but discounted passes are available at the check-in stations. Taking the MBTA Green or Orange Line to get there is easy, too!
Bring Your Pup to One of Boston’s Annual Dog Halloween Parades
Dress your four-legged friend up in a fun costume and head to the Annual Doggone Halloween Costume Parade, which is put on by the Downtown Boston BID. Aside from plenty of adorable dogs-in-costume photo opportunities, there are also plenty of freebies and prizes for those participating, with winners in a variety of categories that range from scariest costume to the best human and dog combo costumes. Water and snacks are provided for both dogs and their owners. The 4th Annual Doggone Halloween Costume Parade will take place on Nov. 1, 2019.
Another option for parading your costumed dog around town is the annual Halloween Pet Parade and Costume Contest in Faneuil Hall. Sponsored by Canobie Lake Park’s Screeemfest, this parade also offers prizes in several different categories and offers goodies from local vendors. The 2019 parade is set for Oct. 26.
Explore Beacon Hill on the Beacon Hill with a Boo! Walking Tour
Whether you plan to trick-or-treat in Boston’s Beacon Hill or not, there’s another way to take in this festive neighborhood on Halloween: the Beacon Hill with a Boo! walking tour. This is Boston By Foot’s most popular tour and has been something those visiting Boston have enjoyed for 30 years. Much like the Ghosts and Gravestones Tour, this one will tell stories about mysteries, murders and other spooky events that took place in Beacon Hill as you stroll along the streets and take in the seasonal décor that surrounds you. You’ll learn all about the city’s witches, Dr. George Parkman and other dark tales. Tickets are $20 and can be purchased here.
Take the Kids to the Franklin Park Zoo for Zoo Howl
Boston’s historic Franklin Park Zoo, just four miles from downtown, is where you’ll find 72 acres of animals ranging including lions, tigers, gorillas, giraffes and more. Around Halloween, from Oct. 26-27, 2019, the Zoo hosts their Zoo Howl event, inviting kids from in and around Boston to trick-or-treat surrounded by the animals, while also participating in other fun activities like a puppet show, costume contest, and howling contest. For candy, the zoo will be giving out varieties made with certified sustainable palm oil in an effort to raise awareness for the palm oil crisis. Tickets to Zoo Howl fall under general admission rates and the event will take place rain or shine.
Run in the Costume Dash 5K on the Charles River Esplanade
If you’re at all into running, the Costume Dash 5K that takes place along the Charles River Esplanade is the perfect fall Halloween activity to participate in. The name says it all—just dress up and run! At this time of year, you can expect beautiful foliage all around as you run along the river—a pretty flat route that welcomes runners of all experience levels. The race is sponsored by the Massachusetts Department of Conservation and Recreation and ends with an after-party for those 21 and over. The Costume Dash 5K takes place on Oct. 26, 2019, and the registration cost is $45, with early bird pricing discounted to $35.
Drink Your Way Along the Official Boston Halloween Pub Crawl in Faneuil Hall
For a taste of Boston’s bar scene with a Halloween twist, sign yourself up for the Official Boston Halloween Pub Crawl, which takes place primarily in the Faneuil Hall area. And this bar crawl isn’t just a one-day affair—it’s three full days of bouncing around from bar-to-bar in your Halloween costume, with this year’s taking place Oct. 31 to Nov. 2, 2019. Stops include Hard Rock Café, Mija Cantina, Howl at the Moon, Side Bar, Wild Rover and many more.
Sample Craft Beers at Hop Culture’s Spooky Brews Halloween Party and Craft Brew Festival
If craft beer is more of your thing, head to Hop Culture’s Spooky Brews Halloween Party and Craft Brew Festival, held on Nov. 1, 2019, at the Innovation and Design Building in Boston. Admission is $60, which comes with unlimited samples from more than 20 participating breweries, including Vitamin Sea Brewing, Lamplighter Brewing Co., Widowmaker Brewing, and many more. The event also has a DJ, food, and costumes are encouraged.
Pick Pumpkins for Seasonal Decor at a Local Farm
Many of the Boston area’s farms and apple orchards also offer pumpkin picking, with one good option being the Belkin Family Lookout Farm, which is 20 miles from the city in South Natick. Here you can pick your pumpkins for Halloween, Thanksgiving, or seasonal fall décor in general while also enjoying cider donuts and a variety of family activities at the farm, including seeing the barnyard animals, face painting, hayrides and more.