10 Spooky Things To Do In Boston This Halloweekend!

by | Oct 28, 2022 | Dirty Water News

Halloween really seemed to creep up on us this year! Looking for last minute plans or just need somewhere to wear that costume that’s been hanging in the back of your closet? Welcome to your weekend plans.

Monday, October 24th – Monday, October 31st – 5:00PM-8:00PM

Pumpkin Painting at Lansdowne Pub – Does your stairway look a little blah? Is it in need of some welcoming decorations for the herd of trick or treaters who will be running up those steps? The Pub has got you covered. From 5-6:30PM or 6:30-8:00PM for $25, guests, or aspiring artists, will be welcomed by a prix fixe menu option and specialty fall cocktails including Tequila & Spice, Pumpkin Spice Martini, and Mulled Wine.

Get creative! For tickets, visit Eventbrite

Friday, October 28th – 6:00-9:00PM

Haunted Brewery Party – They’ve always known their brewery was haunted … why not. make the most of the spooky scene for Halloween. Bring your spooky spirit and join Samuel Adams for a Haunted Brewery Halloween Party! Sing your skeleton heart out during karaoke or give your best ghoul for the costume contest. Ticket includes your first beer ($10 in advance or $15 at the door). Be sure to also book your haunted brewery tours or pumpkin carving tickets.

Friday, October 28th, 29th, 31st 

Trick or Drink Bar CrawlBarCrawlerz is taking Boston by storm this Halloween weekend. This 3 day bar crawl is sure to have you feeling like a true zombie. Registration on Friday will begin at 6PM and end at 11PM, Saturday from 4PM to 10PM, and Monday 6PM to 11PM. Each participating bar will have their own unique drink specials to get guests in the wicked spirit including, but not limited to, Witches Brew, Toxic Shock, Absolut Death, and Boston Strangler Shots. 

​​Participating bars include:

  • Back Bay Social (Registration)
  • The Bebop
  • House Of Blues
  • Rock Bottom Brewery
  • Sidebar
  • Sissy K’s
  • Summer Shack
  • Scholars
  • Wild Rover

Tickets can be purchased here.

Saturday, October 29th – 9:00AM

Allbirds x Boston Road Runners Charity Dash – Don’t let the Halloween festivities distract you from reaching your fitness goals. Allbirds and Boston Road Runners are teaming up to put on a community-run that raises awareness and funds for local Boston-based nonprofits. A portion of the race fees will be donated to nonprofits of the runners choice that improve the community, health, and youth initiatives in the city.

Runners will meet outside of Allbirds at promptly 8:45AM where the race will begin at 9:00AM and conclude at the same location following the 3.5 miles. Coffee will be served to all participants upon completing the course.

To sign up for this charity dash, visit Race Roster.

Saturday, October 29th – 12:00PM-2:30PM

Doggone Halloween ParadeI guess people can’t get enough of adorable dogs dressed up in Halloween costumes. I mean, can you really blame them? This year, the annual Doggone Halloween Parade will be taking over Downtown Crossing in addition to its original location at Summer Street Plaza. Judges will be awarding Best Costume, Scariest Costume, Cutest Costume, and Best Dog & Human Duo.

There will be a plethora of pet-friendly vendors as well as fantastic prizes, treats for all, face painting, fall activities, and more.

Saturday, October 29th – 1:00PM-3:00PM

Hallo-Queen Drag Brunch – Calling all bad witches! Local queens FKA, Pam, Bruiser, and Pristine will be strutting down High Street Place while Halloween themed brunch offerings will be served from multiple vendors.

The $15 ticket includes a reserved seat for the show!

Saturday, October 29th – 3:00PM-5:00PM

Margaritas & Masterpieces – The Painted Burro is kicking off their new series with a Dia De Los Muertos, also known as Day of the Dead, theme. This holiday to honor loved ones is often overshined by the spine-chilling events of Halloween. This Somerville Mexican Kitchen and Tequila Bar is highlighting Mexican culture by hosting a sugar skull painting class. Guests are highly encouraged to channel their inner artist and get creative to truly make their skull one of a kind.

Tickets include:

  • 6″ White Plaster Decorative Sugar Skull
  • An Assortment of Paints & Paint Brushes
  • Creative Inspiration For Painting Your Sugar Skull
  • A Signature Dia De Los Muertos Margarita

And can be purchased through this link

Saturday, October 29th – 7:00PM-2:00AM

The Haunted Mansion at The Greatest Bar – This Friend St. staple will be transformed into a chilling haunted house as their creaky doors will begin to take visitors at 7PM. This night is guaranteed to be filled with drinks, shots, music, prizes, and memories. There will also be a chance for guests to show their creativity in the costume contest where a $1,000 cash prize will be up for grabs. 

For more Halloweekend events at The Greatest Bar visit their website here.

Sunday, October 30th – 11:00AM-2:00PM

Rise and Rumble Donut Throwdown – In the heart of the chic Back Bay neighborhood of Boston, a hint of sweetness will cut threw the terror of Halloween weekend. Making its debut for the first time since pre-COVID, the Himmel Hospitality Group’s Rise & Rumble doughnut competition is bringing a spooky twist to this year’s standoff. The title of “Best Doughnut”, as well as other categories, will be battled for between eight of the city’s top pastry chefs. Chefs from The Banks Fish House, Grill 23, Bistro du Midi & Harvest, Lionheart Confections, The Barbara Lynch Group, Sarma, Mamaleh’s, and The Barrelman will all be dressed in their favorite costume as guests are also encouraged to dress up too.

Guests will be able to attend the event, sample doughnuts, enjoy bites, a non-alcoholic beverage station, a cash bar, and will ultimately get a say in crowning the champion. 

Tickets can be purchased on Eventbrite.

Sunday, October 30th – 2:00PM-6:00PM

SomerStreets Monster Mash – SomerStreets, the open streets concept of Somerville, will be closing off roads to vehicles and opening them up for creepy crawling, zombie walking, and more! This is a free and family friendly event featuring a Halloween Parade, both adult and kid interactive activities, food vendors, craft vendors, music, and more.

Attend one or attend them all – Just make sure you’re choosing wisely… or else…..