Looking to get into the Halloween spirit? Check out this collection of free spooky activities happening in the Boston area this month.
1. Doggone Halloween Pet Parade
Calling all dog lovers! The Downtown Boston Alliance is hosting a puppy costume parade from 12-3 p.m. on Oct. 25. Enter your furry friend for the chance to win a prize! The event is free for all to attend, taking place within Downtown Crossing.
Hosted by Ashlee Feldman from JAM’N 94.5 radio station, this event features live Halloween-themed music covered by the Glass Artists string quartet, local vendors and $1 Ben & Jerry’s ice cream. The Oct. 17 concert runs from 6-8:30 p.m. and is located at The Rocks at 111 Harbor Way in the Seaport.
3. Harvard Book Store After Dark
Looking for a new scary read? On Oct. 30 at 8:30 p.m, Harvard Book Store is hosting a festive book event. Share your favorite scary book or story in a three-minute pitch to receive a coupon for 20% off a purchase! It is also a great opportunity to practice public speaking in a low-stakes environment. Sign up to pitch your favorite story here. Plus, you can enter the costume contest for another chance to win a 20% off coupon. In the final hour of the event, flashlights will be provided for a “lights out” store browsing hour!
Want to get into the Halloween spirit a little early? As part of a Creature Double-Feature, The Substation in Roslindale is hosting a watch party on Oct. 26 for two spooky movies: “Hocus Pocus” at 5 p.m., followed by “The Thing” (1982) at 7:30 p.m. There will be a costume contest with prizes, so get dressed up! Doors open at 4:30 p.m., and you can reserve your free tickets here.
5. Halloween Trivia Night at Boston Public Market
Looking to put your trivia skills to the test? Head to Boston Public Market on Oct. 24 for some Halloween-themed trivia, with two sessions at 6 p.m. and 7 p.m. Winners will take home prizes!
Head to The Anchor in Charlestown at 7 p.m. on Oct. 25 for all things Halloween! From a walk through Boston’s largest urban pumpkin patch to live music, costume contests and more, this haunted waterfront experience is guaranteed to get anybody into the spirit of Halloween!
7. BLAIR 2025 Concert at City Hall Plaza
Calling all music fans! This annual concert and Halloween party features an all-women line-up of DJs and artists. Support female musicians at City Hall Plaza on Oct. 31 from 6-11 p.m., with local vendors and food trucks adding to the fun!
8. Halloween Candy Palate Training at George Howell Coffee
Have a sweet tooth but retired from trick-or-treating? George Howell Coffee, located in the Boston Public Market at 505 Washington St., is hosting a candy taste test on Oct. 30 from 1-2 p.m. Capacity is limited, so grab your free tickets here while you can!
9. “Rosemary’s Baby” Watch Party
Kick off your Halloween festivities with a screening of a horror classic! The Parker Hill Branch of the Boston Public Library, located at 1497 Tremont St., is hosting a watch party of “Rosemary’s Baby” on Oct. 31 at 2 p.m. The library is only a seven-minute walk from the Brigham Circle stop on the Green Line!
10. Halloween Karaoke at The Pearl
Bring your friends and get ready for a fun night of karaoke at The Pearl, located at 67 Guest St. in Boston. The event starts at 8 p.m. on Oct. 30, and costumes are highly encouraged!