October bucket list for Boston, MA

Save this to make the most out of your October plans.

Pumpkins on a door stop in Boston.

Pumpkin season has arrived in Boston.

Photo via @jakehunterallen

Now that everyone is awake for the end of September, let’s talk October festivities. We have crafted a bucket list for things to do to get the most out of the spookiest month of the year.


Scare Leave | All month | Times vary | Shore Leave | Price of purchase | Visit the Halloween pop-up for a scary good time and a spooky cocktail or two.

Harvest Party | Wed., Oct. 12 | 5:30-10 p.m. | Boston Public Market | $50+ | Shop the local vendors + see New England’s largest pumpkins.

Pumpkin Carving Bash | Sat., Oct. 22 | 11:30 a.m. + 2 p.m. | Sweet Cheeks Q | $26 | Tickets include a pumpkin, a carving kit, painting kit, and either a nonalcoholic drink or an Angry Cheeks cocktail for pumpkin carvers over 21.

Ghastly Gala | Sat., Oct. 22 | 2-8 p.m. | Bone Up Brewing Company, 38 Norman Street, Everett | Free | Things will get spooky — shop the marketplace at 2 p.m. and live music begins at 6 p.m.

Howl-O-Ween Contest | Sun., Oct. 23 | 3-4 p.m. | Break Rock Brewing, 534 Victory Road, Quincy | $5.00 - $10.00 | Sign up your pet to compete in this costume contest for a howling good time.

Scaryoke | Tues., Oct. 25 | 9 p.m. | Painted Burro | Free | Head to Davis Square for a night of festival cocktails, monster sing-a-longs, and a costume contest.

Stranger Things Party | Sat., Oct. 29 | 9 p.m. | Liberty Hotel | $65+ | Head to the upside down for a night of specialty cocktails, dancing, and live music from DJ Frank White + DJ Joshua Carl.

Hocus Pocus Drag Brunch | Sat., Oct. 29 | 11 a.m. | Summer Shack | $20 | Tickets will sell out for this performance so get yours before they disappear.

Doggone Halloween Parade | Sat., Oct. 29. | 12-2:30 p.m. | Downtown Crossing | Free | Come as you aren’t for this annual pet parade.

Halloween bat cookie baking class | Sun., Oct. 30 | 11 a.m. | Flour Bakery + Cafe | $150 | Spots are scary limited for this baking class with pastry chef Coco Maniscalco.


  • Take in the fall foliage at one of these local spots. Peak foliage is expected to happen this month.
  • Cider season has finally arrived. Here are four local spots to indulge in the treat, in both donut + drink form.
  • Visit a pumpkin patch to pick your pumpkin and send us your best carvings. Stay tuned for our guide to the best patches.
  • Get lost in a corn maze like the Sauchuk’s Corn Maze, which features a Big Papi design this year.
  • Gather your ghouls and visit one of these 16 historic cemeteries for a haunting experience.
  • Spend a day in Salem and run amok at these Hocus Pocus locations.
  • Take a ghost tour or tour the crypt below Old North Church, featuring 37 vaults entombed from 1732-1860.

Did we miss your favorite October activity? Let us know and we can add your recommendation to the list.

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