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A free Oktoberfest in Southie, then Halloweentown

Castle Island Brewing pours a free Oktoberfest in Southie on the 17th. Friday is a scare in the Seaport, with pumpkin painting on Newbury later in the month.

Michelle McCormack

Michelle McCormack

Michelle is the founder of Secret Boston and a Producer. Born and raised on the mean streets of JP, she was once chased by a lion in Africa while on assignment for Town & Country Magazine.

A free Oktoberfest in Southie, then Halloweentown
  • Play It By Fear

    Fri, Oct 16 · 6:00–8:00 PM

    The Rocks at Harbor Way · Boston

    Play It By Fear

A string quartet plays the slasher themes

Play It By Fear is the night for a costume without a ticketed maze. It is Friday, October 16, from 6:00 to 8:00 p.m. at The Rocks at Harbor Way, 111 Harbor Way. The Seaport’s own listing has candlelight caricatures, a tarot table, and a photo booth. DJ Brian Halligan starts at 6:00 p.m. JAM’N 94.5 host Ashlee Feldman is the host. At 7:00 the Glass Artists string quartet plays Halloween classics and themes from slasher films, an hour after the DJ starts. A stand will be scooping $1 ice cream, and Union Square Donuts and The Sweetish Fish are on site. Seaport VIP Insider deals that night run from 5:00 to 9:00 p.m. The list includes Flight Club, Levain Bakery, and Puttshack, along with other Seaport businesses. The page does not list a ticket price, so check before you treat the caricature as free.

A free Oktoberfest on Old Colony Ave

Castle Island Brewing’s Oktoberfest is Saturday, October 17, from 11:00 a.m. to 8:00 p.m. at 10 Old Colony Ave in South Boston. It is free, and you have to be 21. The day is German lagers, a make-your-own pretzel necklace, hot beer poking, and oompah music from Kier Byrnes. The listing asks for lederhosen and dirndls.

A mixer with no timed dates

Date Faster’s Halloween singles mixer is Saturday, October 17, from 7:00 to 9:00 p.m. It is 21 and over, and there are no timed dates. The page lists name tags, hosts, drink specials, and a game of Two Truths and a Lie. The prize is a ticket to another Date Faster mixer. Drinks are bought at the venue and are not included. Costumes are encouraged. Ticket totals run from $9.30 to $23.17. You can ask for a refund up to 7 days before the event, or exchange the ticket for another date. The calendar lists Howl at the Moon, 184 High Street. The description on the same event also says the venue is to be announced. Read the ticket page the day you go, and do not plan the night around the pianos at Howl at the Moon until that line is gone.

  • Harvest Party

    Thu, Oct 22 · 5:30–7:30 PM

    Boston Public Market · Boston

    Harvest Party

A fundraiser after the market closes

The Boston Public Market Association’s Harvest Party is Thursday, October 22, from 5:30 to 7:30 p.m. at Boston Public Market, 100 Hanover Street. The market closes at 3:00 p.m. that day for the party. Tickets cover unlimited tastings from market vendors, local beer, wine, and spirits, plus live entertainment and a silent auction. Individual tickets are sold through Zeffy, so the nonprofit keeps the full price. Sponsorships and in-kind gifts are open too.

  • Halloweentown

    Sat, Oct 24 · 3:30–8:00 PM

    the TRACK at New Balance · Boston

    Halloweentown

A free screening at Boston Landing

Boston Landing screens Halloweentown indoors on Saturday, October 24, at the TRACK at New Balance, 91 Guest Street. Admission is free and an RSVP is required. The pre-party is at 3:30 p.m. and the screening is at 5:30 p.m. It is all ages. The page linked here lists 3:30 to 8:00 p.m. The Eventbrite listing ends at 7:00 p.m. This entry uses 3:30 to 8:00 p.m. Refunds can be requested up to 7 days before the event.

  • PruBoo

    Sun, Oct 25 · 11:00 AM–1:00 PM

    Prudential Center · Boston

    PruBoo

Trick-or-treat at the Prudential

PruBoo is a free family Halloween event on Sunday, October 25, from 11:00 a.m. to 1:00 p.m. at the Prudential Center, 800 Boylston Street. Kids trick-or-treat at more than 30 stores and restaurants. The page also lists face painting, Halloween crafts while supplies last, magic shows by Robert Clarke at 11:30 a.m. and 12:30 p.m., and The Stacey Peasley Band. A trick-or-treat bag is a $5 donation to Boston Children’s Hospital. The band is listed from 10:30 to 11:30 a.m. and from noon to 1:00 p.m. The 10:30 start is before the stated 11:00 a.m. start.

Paint a pumpkin on Newbury Street

Sonsie hosts pumpkin painting on Monday, October 26, from 6:30 to 8:30 p.m. in the downstairs Wine Room at 327 Newbury Street. The ticket is $44.52 and includes a pumpkin, paints, a welcome mocktail, and light bites, and you take the pumpkin home. Food at Sonsie is 20 percent off before or after the event if you stay to eat. Refunds are available until seven days before the night.

A costume rave at a secret location

The location is still a secret. Experience Halloween Night 1 is a costume rave on Friday, October 30, from 9:00 p.m. to 2:00 a.m., and the venue is listed only as TBA. Experience and Techno Brooklyn are hosting. Briela Veneno, Crossbow, and L9 play. Costumes are encouraged. It is 21 and over, and tickets are listed from $25.

A costume contest at Faneuil Hall

Ned Devine’s Halloween party is Saturday, October 31, from 8:00 p.m. to 2:00 a.m. at 1 Faneuil Hall Marketplace. There is a DJ and a costume contest. First prize is $300 and the runner-up prize is $200. Guests have to be in the door by 10:00 p.m. It is 21 and over with a valid ID. Angry Orchard is the sponsor. Sales are final. The poster says advance tickets are $10. Eventbrite’s total is $11.54.

Trixie Mattel DJs at Royale

Trixie’s Halloween is a 21-and-over dance party on Saturday, October 31, at Royale, 279 Tremont Street. Doors are at 9:00 p.m. Tara Dikhof opens, Trixie Mattel DJs, and the night includes pop-up performances from Boston drag performers plus a $1,000 costume contest hosted by Trixie. Katya is not performing. Presented by Royale Boston. Ticket sales are final. A promo code, DISCO, is $5 off. It does not apply to every show.

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