Halloween in Boston

Boston’s coolest destination for all things food and drink offers 29,000 sq ft of socially distanced fun at 401 Park in the Fenway. This weekend, get your tickets in advance for the Negroni Flight or Fright Night (Oct 30, 5-6pm and 6:30-7:30pm), or stop by for Halloween fun on Oct 31.

And now through the end of November, stop by to check out 60 killer images from local legend Phillin Phlash; the Market's first-ever art show is free to visit.

Keep an eye on the @timeoutmarketboston IG handle for specific events and offerings. Saturdays and Sundays feature a make your own Bloody Mary Bar, letting you chose your spirit and customize to your heart's content. (Think pepperoni from Michael Schlow's and donut holes from Union Square Donuts.)

First order of Halloween business is to find the perfect pumpkin to demonstrate your carving skills. Skip the store bought pumpkins and head to one of these farms near Boston where you can pick your own from a patch surrounded by idyllic farmland. 

Salem is at its busiest during the month of October, when history and horror buffs head to the site of the witch trials. Check the city’s Haunted Happenings website for the full schedule. You can tour the Witch House or take a Ghost Tour any time of year, but there’s something extra spooky about being there in October. This year, the Haunted Happenings Market goes virtual, so you can check it out from anywhere.

Explore the spooky side of Boston on the Trolley of the Doomed. On this 90-minute tour, you’ll hear tales of the Boston Strangler, of murders and executions that took place on the Boston Common, and of paranormal activity at the Omni Parker House. Most of the tour is aboard the trolley, but you’ll also walk through two of the oldest burial grounds in the city and visit the site of a notorious grave-robbing scandal. The tour is available year-round, but Halloween is the best time to go (book tickets early), especially in costume.

Enter the woods in Westford and hope that you make it out alive. Witch’s Woods features seven different attractions. A ticket is required for the main attractions—Haunted Hayride, Castle Morbid, Horrorwood Chamber of Chills, Jackolantern Jamboree, and Vampire Passage.

You can still get your fix of spooky ghost tours this year, from the comfort of your own home. With GhostFlix, you can watch pre-recorded guided ghost tours from cities around the country, or tune in for eerie live-streamed tours. From Boston to New Orleans to Portland, OR and more, get ready to exlpore the spookiest American cities.

While the Mansion will not be open this year, Abingdon's spookiest spot is instead presenting a drive in experience. Each weekend features a double feature of horror on screen from old school classics to modern day terror. Stay alert - creatures will be roaming the grounds waiting for the right moment to make you scream. A special menu will be available from the Abington Ale House, delivered right to your car.

Boston Ghosts offers a chilling look into a more ghastly side of Boston. There are endless ghost stories to tell, from religious quarrels to fiery locals. You'll take a tour through downtown Boston’s most haunted hotspots and explore both the paranormal and historical worlds.

One of the oldest and most historic hotels in Boston, the Omni Parker House is said to be haunted. Originally built in 1855 and then rebuilt in 1927, the hotel is a stop on many ghost tours. There have been reported sightings on the 9th and 10th floors of a bearded gentleman dressed from the Colonial era, and the 3rd floor has been said to have its share of paranormal activity as well. 

At the top of your October shopping list, of course, is to get yourself a costume. The Garment District has everything you can think of for the perfect Halloween costume—witches, ghouls, monsters, plus any number of “sexy” outfits and all kinds of masks. Wallet-watchers scared off by brand new costumes can peruse the thrift section for retro finds.