Play it by Fear will take place on Friday, October 17th!

All are invited to step into the shadows and immerse themselves in a Halloween celebration like no other! Boston Seaport by WS welcomes back Play It By Fear, their annual Halloween celebration, this coming Friday, October 17 from 6:00pm – 8:30pm.

The Rocks at Harbor Way will transform into a spellbinding Halloween destination as JAM’N 94.5’s Ashlee Feldman hosts a frightfully fun evening filled with music, mischief, and memorable moments.

Set against a backdrop of eerie enchantment, this one-night-only experience features:

  • one hour live performance of Halloween slasher themes and classic hits by the Glass Artists string quartet
  • Beer and wine available for purchase from Castle Island Brewing
  • Live tunes from DJ Brian Halligan
  • Tarot card readings, spooky characters by local artist Maggie Lin, a haunted house themed photo booth and a towering pumpkin arch 
  • Sweet and savory bites from Puffy Clouds
  • Ben and Jerry’s will be on-site serving $1 scoops, or grab takeout from one of our favorite neighborhood haunts
  • Trick-or-treat at booths from various fan favorite neighborhood businesses like Pressed Cafe, Bond Vet, Framebridge, and more
  • The exclusive Nightmare Before Christmas jewelry collection from Little Words Project, available to purchase
  • A themed Seaport merch collab with artist Bill Crisafi, “Ghoul Dinner” and “I Am The Treat” is available for pre-purchase here, and will be available for purchase on-site with all proceeds going to BAGLY, (Boston Alliance of LGBTQ+ Youth)
  • Guests who stop by the Seaport Insider tent will receive a Seaport puffy pouch, redeemable with the download of the Seaport Insider app and a credit card linked. VIP members can redeem a Seaport pop socket charger for 800 points. Shoppers are encouraged to download the Insider app today to start earning perks from their favorite neighborhood retailers.
WHEN: Friday, October 17, 2025 from 6:00pm – 8:30pm

WHERE: The Rocks at Harbor Way, 111 Harbor Way, Boston, MA 02210

ATTENDANCE: Free. For more information on Play It By Fear and to RSVP, please visit the event page.

Photo Credit: Boston Seaport by WS, Photographer Eric Levin

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