Something Spooky Is Brewing in Boston Seaport Play It By Fear Returns Friday, October 16

Ashlee Feldman and the Glass Artists Host a Night of Live Music, Devilishly Good Bites and Halloween Fun at The Rocks at Harbor Way
Guests are invited to venture, if they dare, to Boston Seaport for Boston Seaport’s annual haunted Halloween celebration, Play It By Fear, on Friday, October 16, 2026, from 6:00–8:00 p.m.
For one night only, The Rocks at Harbor Way will take a turn for the spooky as Ghost HOST Ashlee Feldman leads an evening filled with live music, and plenty of tricks, treats and surprises. The night’s frightfully fun lineup includes:
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A one hour live performance of Halloween slasher themes and classic hits by the Glass Artists string quartet followed by DJ Brian Halligan to keep the music going.
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Seaport Insiders have exclusive access to tarot card readings, spooky character drawings by local artists Nick Shea and Rene James, and a haunted house-themed photo booth.
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Trick-or-treat with neighborhood favorites including The Sweetish Fish and Union Square Donuts.
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Ben and Jerry’s will be on-site serving $1 scoops, or grab takeout from one of a neighborhood haunt for a spooktacular picnic.
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Download the Seaport Insider App for devilishly good deals and a free surprise treat at the Insider tent. Link a credit card in the app to claim your treat.
WHEN: Friday, October 16, 2026 from 6:00pm – 8:00pm
WHERE: The Rocks at Harbor Way, 111 Harbor Way, Boston, MA 02210
ATTENDANCE: Play It By Fear is free and open to the public. For more information on Play It By Fear and to RSVP, please visit the event page.

Maureen Dahill is the founder of Caught in Media. Once a longtime wardrobe and prop stylist for brands such as Rue La La, TJ Max & Hasbro, she is a devoted lover of vintage clothing, Martini Mondays, Castle Island, AND a 4th generation South Boston native. Mother of three, married to Peter G.

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