Things To Do in Massachusetts During the month of October

There are so many fun events around the state this month but sometimes it can be hard to find them! Today I’m sharing a list of a bunch of events happening this month in Massachusetts! If you’re looking for something to do on the weekends or you just want to participate in more events around you, this list is the perfect place to find something for everyone to do! Some of these events are free but some need tickets purchased. If you click the link, it’ll bring you to the website where you can purchase tickets for that event!


October 1:
Oktoberfest at Cisco Brewers Seaport

Room to Grow Fall Fest

October 2:

3rd Annual Cider Donut Run

Fall Floral Arranging Workshop with Central Square Florist!

Brick or Treat at Legoland *every day until October 31st*

Secure the Shadow: Spirit and Post-mortem Photography at The House of the Seven Gables

October 3:

New England Witchcraft Tales hosted at Hamilton-Wenham Public Library

Enchanted Garden *every day until November 10th*

Mean Girls Trivia

Bit Bar Boo Bash

October 4:

Fall Colors Kayak Tour

Harpoon Octoberfest 2019

Lanterns in the Village 2019

Topsfield Fair *until October 14th*

MFA Film: The Cell

Not So Spooky Halloween

October 5:

Harry Potter Murder Mystery Dinner Show

Boston Food Truck Festival at The Rose Kennedy Greenway

Ghastly – The Oddity & Horror Marketplace in Lowell, MA

90’s Bar Crawl

Apple Festival Hosted by Yankee Candle Village MA

Lanterns In the Village

Harry Potter Trivia

Boston Public Library Book Sale

October 6:

Fall Foliage River Cruise *multiple dates*

Harpoon Dogtoberfest

Pilates on the Patio

Strangest Things: A Murder Mystery Dinner Party

Harvest Fest at Linscott Park in Swampscott, MA

October 7: 

Silent Book Club Hosted by Trident Booksellers & Cafe

300 Years of the Clough House at Old North at Old North Church & Historic Site

October 8:

Lauv ~how i’m feeling~ Tour / Boston

Hocus Pocus Mom/Friend & Me Paint Event/ Taunton

October 9: 

Post Malone – Runaway Tour

Movie Night: Teen Witch hosted by Far From The Tree Cider

Hocus Pocus Trivia & Costume Contest Hosted by The Wine Lab

October 10:

LeakyCon 2019 Boston

FSPL Presents: Best Booksale Ever! hosted by Friends of the Somerville Public Library (MA)

Candle Maker at Nu Kitchen

Joe Hill & Stephen King

October 11:

Harbor Islands Fall Foliage Lunch Cruise

October in Salem Night Market by Creative Collective Merchant Marketplace

Sara Bareilles: Amidst The Chaos Tour 2019

Mason Ramsey: Hows Ur Girl & Hows Ur Family Tour Pt. II

Halls of Darkness: Fears & Phobias by Hammond Castle Museum

Haunted Harbor at Salem Horror Fest

Tales From the Crypt – 30th Anniversary Tribute

October 12:

New England Chocolate Festival

Brick Safari Kick-Off Celebration

Autumn Spirits Weekend by Tower Hill Botanic Garden

Harry Potter Adventure-POP UP

Carrie Movie Night at Deacon Giles Distillery

Fall at the Hall Hosted by Faneuil Hall Marketplace

Howl-o-Ween Pet Parade

October 13:

Nervo at Mémoire

Wizards & Witches Dinner

Cranberry Festival at Edaville Events Field

Haunted Harbor at Salem Horror Fest

Dante’s Inferno Screening

October 14:

Opening Our Doors Celebration

Harry Potter Trivia Hosted by Captain Crew’s Question Cruise and Far From The Tree Cider

Indigenous Peoples’ Day at the MFA

October Book Swap! Hosted by Trident Booksellers & Cafe

October 15:

Haunted Road Trips of New England Hosted by New England Curiosities at Tewksbury Public Library

Natasha Bedingfield

The Shaw 54th: Restoring the Memorial and the Dialogue on Race

Everett Fun Run! by Night Shift Brewing

October 16:

The Early November w/ Have Mercy and OWEL at Brighton Music Hall

Movie Night: Harry Potter Hosted by Far From The Tree Cider

Panel Discussion: Slavery & its Legacies at Old North Hosted by Old North Church & Historic Site

October 17:

The Great Pumpkin Roadshow – Boston Hosted by Elysian Brewing

MAMMA MIA! An ABBA & 70’s Disco’s Dance Party

NOTCH Pumpkin Carving Contest 2019

October 18:

Taylor Swift Night at The Point

Fall Pumpkin Float 2019 at Frog Pond

Paint Nite at Mount Vernon!

October 19:

Boston Hard Cider & Doughnut Fest at The Greatest Bar

Boston Book Festival Sisters in Crime Panel! at the Boston Public Library

Rockport Harvestfest Hosted by Rockport Exchange

Disco Night


Pumpkin Ball Hosted by Yankee Candle Village MA

Boo at the Zoo

Spooktacular Open House at NEAS Hosted by Northeast Animal Shelter

October 20:

Fall Foliage River Cruise

SomerStreets: Monster Mashed-Up in Somerville, MA

Spooky Cheese Night

Boo at the Zoo

Head of the Charles 2019

American Craft Fair by Tower Hill Botanic Garden and Worcester Center for Crafts

Patio Pumpkin Carving!

October 21:

Hocus Pocus Trivia Hosted by Captain Crew’s Question Cruise and Far From The Tree Cider

Dr. Neil deGrasse Tyson: Letters from an Astrophysicist at the Chevalier Theater

FALL FUN! Hosted by Brush Strokes Art Studio

October 22:

BCR Flatbread Benefit in Somerville Hosted by Black Cat Rescue and Flatbread Somerville

Spooky Somerville: GrownUp StoryTime at Remnant Brewing

Crafternoon: Halloween Painted Rocks

Fall Harvest Festival with Lexington Farmers Market Hosted by LexFUN!

October 23:

An Evening with Gregory Maguire

Movie Night: Hocus Pocus Hosted by Far From The Tree Cider and Speakeasy Donuts

Plant Nite – Autumn Garden!

Boston Music Showcase & Wine Night

6th Annual Downtown Trick or Treat Hosted by Whitelam Books

October 24:

Soul Searchin’ with Jamila Woods

Nightmare on Main Street in Peabody, MA

It’s All Hocus Pocus – Halloween Creative Workshop

4th Annual Harvest Party

World Of Dance Live! Tour Orpheum Theater

Glow Boston Halloween | Dia De Los Muertos

October 25:


MFA Late Nites

Tomes of Terror: Beyond Grimm

BSSC Halloween Party 2019

Corn Maze and S’mores

Haunted House

Scotty Sire – What’s Going On Tour at The Paradise Rock Club

Dead Herring: A Cemetery Symbolism Scavenger Hunt

October 26:

The Witches Almanac Magickal Masquerade Ball

Basic Witches Halloween Brunch at City Tap Boston

Halloween Pet Parade & Costume Contest at Faneuil Hall

Taste of Maze

10th Annual Halloween Stroll Hosted by Stoneham Chamber of Commerce and Stoneham TV

Halloween Bar Crawl Boston

Red Lantern Presents: Halloween ft. Music by Soluna

Boston Costume Dash 5K

Trick or Treat at The Street

West Medford Halloween Block Party

Day of the Dead Halloween Party

Pumpkin Palooza at Lawn on D

October 27:

Timmy Trumpet at Mémoire – Halloween Weekend

Movie Night at Deacon Giles Distillery Hosted by Speakeasy Donuts and Deacon Giles Distillery

Gluten-Free New England’s Greater Boston Expo!

Castle Island Association’s 37th Annual Halloween Celebration Hosted by Castle Island Association

Woburn Host Lions Club Halloween Parade Hosted by Woburn 502

19th Annual Halloween Horror Marathon

Monster Mash Sing Along Toddler Time Hosted by Sky Zone Everett

Fall Colors Ride Hosted by Bike to the Sea

Trunk or Treat

October 28:

I Love Mondays feat. R3HAB 10.28.19

Hocus Pocus at Harpoon Hosted by Harpoon Brewery

Hocus Pocus Trivia Hosted by The Castle: A Board Game Cafe

Nocturnal Animal Pumpkin Trail

October 29:

Dia De Los Muertos Paint Party

RuPaul’s Drag Race – Werq The World Tour 2019 at the Boch Center

Everett Fun Run! by Night Shift Brewing

Halloween Slime & Cupcake Making/Costume Contest

October 30:

Movie Night: The Witches Hosted by Far From The Tree Cider and Speakeasy Donuts

Halloween Candy & Beer Pairing Hosted by Bone Up Brewing Company

Trident Cinema: Hocus Pocus! Hosted by Trident Booksellers & Cafe

Movies Under the Dome: The Blair Witch Project

Halloween Silent Disco x Bit Bar Salem Feat. DJ Yosay

October 31:

Haunted Halloween Costume Cruise

Halloween Costume Party

Halloween Candy & Beer Pairing Hosted by Bone Up Brewing Company

Trivia in the Tap Room – Halloween Edition Hosted by Harpoon Brewery

Tomes of Terror: Beyond Grimm

Trick or Treat at Melrose Businesses Hosted by Melrose Chamber of Commerce

Ned Devine’s Halloween Party 2019

Annual Doggone Halloween Costume Parade

The Rocky Horror Picture Show (on 35mm)

Throwback Halloween Party with DJ Rolo

Halloween Music Bingo with the Haverhill Exchange Club Hosted by Haverhill Exchange Club and Bradford Country Club



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