Halloween in Boston celebrations start at least a month before the actual event on October 31st.
After all, Boston has some of the country's oldest graveyards, haunted tales, and scary events, plus great places to shop for Halloween costumes. If you visit Boston during October, be sure to take part in these Halloween events!
Here are some of the best places to celebrate Boston Halloween . . . starting with graveyard tours and ghost stories.
Not just for Halloween, Boston's nightly Ghosts and Gravestones Tour combines a trolley ride with walking to visit the city's scariest sites.
Costumed "gravedigger" guides show you the darker side of Boston. They'll entertain you with haunted tales about the city's earliest days and strange discoveries - the mysterious North End tunnels, the unexplained Day of Darkness back in 1780, and the haunting ghost of Boston Harbor, the Lady in Black. And then there's the scariest part of the tour . . . a chilling visit to 2 of Boston's oldest graveyards, accompanied by tales of the macabre.
Ghosts and Gravestones tours fill up fast around Halloween in Boston - so make your reservation now!
When: October 31, 2013; 6pm - 9pm
Where: Hampshire House,
Part theater, part musical event, and part culinary adventure, Dining in the Dark presents a memorable evening at Hampshire House, the special occasion dining venue in a magnificent Beacon Hill mansion. You'll put on a blindfold before entering the candlelit dining room, and all your other senses will take over as you savor the exquisite meal, stirring music, wonderful story, and of course, your dining companions.
You can also enjoy a special Thanksgiving Dinner at Hampshire House
Boston pubs and hotels get into the Halloween spirit with prizes for best costumes, live music and/or DJs, and shows. Tickets usually required (call in advance to check); most are 21+. Several Halloween parties and events to check out:
Liberty Hotel (215 Charles Street, 617-224-4000) - Night of the Living Dead extravaganza with DJ, specialty drinks, and costumes; Saturday, October 27, 8pm, tickets $35, or included in Liberty's special Halloween Package (includes 2 party tickets, parking, and breakfast for 2, plus a luxury room. November 2, 2013 Check rates.
The Greatest Bar (262 Friend Street, West End near TD Garden, 617-335-5582) hosts Haunted House V - Enjoy sounds by Breeazy and explore 4 floors of terror: The Crypt, The Terrace, the Keepers Room, the Haunted Attic - Saturday, October 26, 2013, 8pm.
Church of Boston (69 Kilmarnock, Fenway neighborhood, 617-236-7600) - Clandestino Halloween Party 2013 - Saturday, October 26, 8pm; tickets $15/$20 after 10:30pm
Lansdowne Pub (9 Lansdowne St, Fenway, 617-247-1222) - Halloween Ball with live music by Bearfight on October 31; shows start at 9pm.
Half-price (and less!) tickets to Halloween events and shows are available through Goldstar. Check out these offiers:
Boston Haunts Pub Crawl - Wear your best costume!
Hairy Tales - Adults-only show featuring gothicized versions of Sleeping Beauty (Vampirilla) and Little Red Riding Hood at Boston Center for the Arts
Frightful Fridays - A ghostly walking tour at Gore Mansion will take you back on a spine-tingling journey to 1806
Sinners and Saints Halloween Cruise - 21+ 3-hour cruise in Boston Harbor - compete in the costume contest!
Based on my own admittedly non-scientific observations, Beacon Hill's historic homes display some of the most colorful and lavish Halloween door and window decorations in the city. You can easily stroll through the neighborhood on your own - Chestnut and Mt Vernon Streets are great starting points.
Even better - join one of the popular Beacon Hill photography tours. Your guide will make sure you see the neighborhood's famous cobblestone lanes and other photo-worthy, give you tips on how capture the best shots, and entertain you with stories about the famous residents - past and present - who live here. Of course, you can take this tour throughout the year, but having lots of Halloween decorations to photograph adds to the fun!
You'll encounter the dead, the undead, and everything in between at the last, biggest, and perhaps the best SoWa Open Market of the season.
With over 130 vendors and a $250 price for the best costume, this popular outdoor market will be packed with ghouls, goblins, and the macabre - along with wonderful things to buy and take home.
Live music, pumpkin carving, food trucks, and lots more make this the perfect pre-Halloween destination - plus if you're smart, you can do all of your holiday shopping before the market closes for the season.
Date: Sunday, October 27, 10am-4pm
Location: 460 Harrison Ave, Boston's South End
Historic graveyards dating back to the 1600s enhance Halloween in Boston. You can easily explore these Freedom Trail sites on your own.
Granary Burying Ground contains the remains of some of the greatest Revolutionary War heroes. One of Boston's oldest historic sites, it is where you'll find tombstones and grave markers for patriots Samuel Adams, Paul Revere, and the 5 Boston massacre victims.
A block away is King's Chapel Burying Ground, Boston's oldest cemetery. Many of the first generation of English Puritans who settled in Boston are buried here. Intricately carved seventeenth century headstones show Time wrestling with Death.
And, if you enjoy scary ghost stories, King's Chapel Burying Ground is supposedly haunted by Captain Kidd, hanged for piracy in 1701.
Of course, like many other Boston Halloween tales, that story may not actually be true.
Excellent information signs at both of these burying grounds on Boston's Freedom Trail will guide you as you discover where all the bodies are buried.
Each year, ImprovBoston creates a new musical comedy full of squirting blood (aka red corn syrup), juvenile humor, tasteless dialog, and catchy tunes to entertain and gross out Halloween fans.
GoreFest 11 is a special 1-night only cabaret-style musical celebrating the macabre.
Expect plenty of laughs and lots of splattering blood, not all of which lands on the actors. Don't wear your good clothes.
ImprovBoston's Halloween romp aspires to be inappropriate for people of all ages, and therefore is not for children, the squeamish, the easily offended, or anyone with a sense of decency.
But if you love this kind of comedy, not just for Halloween, get your tickets now. And you may also want to check out other best Boston comedy clubs.
When: October 24 - 31
Tickets and more information: Check ImprovBoston's website - or call 617-576-1253 for times and reservations
Address: ImprovBoston Theater, 40 Prospect Street, Cambridge (Central Square)
Nearest T station: Red Line/Central Square
If you're looking for a family-friendly Halloween event in Boston, Pru Boo is the biggest Halloween party in the city for toddlers to 12 year olds. The Shops at Prudential Center host this annual event, with all proceeds going to a non-profit partner to benefit children.
Let your children don their scariest costumes and bring them to this safe and fun event featuring costumed characters, concert, pumpkin decorating, trick-or-treating, face painting, magic tricks, and much more. They'll have tons of fun, you can browse for great shopping deals throughout the surrounding shops, and babies who need help the most will benefit.
Date: Weekend before Halloween - check the Boston Event Calendar for updated details
Location: Shops at Prudential Center, Boston's Back Bay neighborhood
Nearest T Station: Green Line/Pru Center
Cost: $4 per child (12 and under)
Pumpkin carvers of all ages are invited to exercise their skills on Saturday, October 12, 2013 from 12noon - 3pm at 75 Chestnut, one of Beacon Hill's most charming neighborhood restaurants. Carve, paint, and decorate your pumpkin, and then take it home with you. Reservations required - 617-227-2175.
The pumpkins are complimentary - but plan to indulge yourself with some of 75 Chestnut's special fall fare - pumpkin bisque, cranberry apple crumble, and for the grown-ups, the special apple, peach, and pumpkin martinis made from locally-grown produce.
On October 31st starting at 5pm, 75 Chestnut invites visitors to stop by in costume and enjoy various Halloween specials and wicked witches brews, including the featured drink of the night: a Halloween Spider Martini made from secret ingredients
75 Chestnut is owned by Thomas Kershaw, who also owns the "real" Cheers (also known as the Bull and Finch) on Beacon Street.
During the weeks before Halloween, Boston party-goers and power shoppers head across the river to the Garment District in Cambridge for budget costume choices. In addition to this funky secondhand clothing store's usual vast array of recycled costumes, retro fashions, and vintage gems, you'll find a great assortment of wigs, swords, masks, body paint, and other Halloween gear in the month or so before Boston's favorite holiday. Cheap prices - so you'll still have plenty of $$s left for buying candy.
My best insider tip for the Garment District: Go early to beat the crowds and get the best selection!
Address: 200 Broadway at Portland Street intersection, Cambridge
Open: Daily; call 617-867-5230 for hours
Nearest T station: Red Line/Central Square
Dorothy's surely qualifies as the biggest costume shop in Boston, if you measure by the huge quantity of costumes and accessories cramming every aisle, floor to ceiling.
In the weeks before Halloween, Boston shoppers line up for the chance to survey the offerings in this Fenway specialty shop on the edge of Back Bay between Berklee College of Music and the Christian Science Mother Church, and almost next to Bodega, one of Boston's famous "insider" shopping secrets.
Dorothy's almost bursts with every costume and accessory imaginable, and most are very reasonably priced - for example, sturdy fishnet stockings run about $5. Other stellar finds include hats, fake mustaches, wigs, costumes, cheap cowboy boots, outrageously fake jewels, and stilettos.
Most costumes are for adults. You'll want to hit the gym before strutting around in many of them. Don't bring your children unless you want amuse fellow-shoppers as you attempt to explain x-rated details in family-friendly language.
This family-owned shop has been here since 1947, and for the fashionably adventurous, it's not just for Halloween. Boston is a more interesting place to party because of it.
Address: 190 Massachusetts Ave, near Huntington Ave, Back Bay
Hours: Open daily; call 617-262-9255 for hours
Nearest T station: Green Line/Hynes
Almost directly across the street from Dorothy's Boutique and Bodega is Army Barracks, a well-stocked Army-Navy type store specializing in vintage uniforms and accoutrements.
Army Barracks is hard to miss - just look for the life-sized models out front. Like Dorothy's and the Garment District, it's not just for Halloween - but you'll find plenty of ways to transform your image here.
Address: 173 Massachusetts Ave, Back Bay
More information: 617-437-1657
Nearest T station: Green Line/Hynes
Take a day trip or even a long weekend from Boston to experience Halloween in Salem, Massachusetts, also known as the "Witch Capital" after the infamous witch trials of 1692 led to the execution of 20 people and 2 dogs.
A bus tour to Salem from Boston is an easy option for getting there, plus you'll have plenty of time to explore, visit a witch museum, and see other famous sights in the area.
Check out Halloween in Salem for more about the witch museums. To find this year's date for Salem's Haunted Happenings Grande Parade, usually held in early October, check the Boston Events for October.
Get Our Free Newsletter
Boston in October