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Halloween Happenings in Southie

The Great Pumpkin Carving Event at Lincoln:
Lincoln is getting in the Halloween spirit with two nights of pumpkin carving, pumpkin themed drinks and food specials!  Carving events happen on Monday, October 17th and Monday, October 24th.  There will be prized for best designs! Tickets are $20 and include one pumpkin and one pumpkin carving kit! You can purchase tickets here! 

Children’s Magical Halloween Castle:
Take a magical journey! A local favorite, The Children’s Magical Halloween Castle, takes place on Saturday, October 22nd and Sunday, October 23rd 12pm-4pm each day.  The Castle Island Association transforms Fort Independence at Castle Island into a family friendly Halloween showcase.  Enjoy magic tricks, storytelling, popcorn and treats.  Don’t forget to wear your costume.This event is free and open to the public.

Neponset Great Pumpkin Float:
Did you know pumpkins float?  Well, apparently the DCR did because it’s time for the Annual Neponset Great Pumpkin Float at Pop John Pall II Park in Dot on Thursday, October 20th at 6pm – registration starts at 5:30pm. This wildly popular family event encourages you to bring a 6-8 inch hollow & carved pumpkin to the event. Each jack-o-lantern will have a candle inserted and lit before being launched en mass in the water at 6pm.  Floats and candles will be provided.   Free hot cocoa and candy treats will also be provided. The event is free and no registration is required.  This is the 14th year of this Dorchester tradition when hundreds of kids in costumes and their families participate in the floating parade of pumpkins!

Pumpkin Float 2016:
Bring the entire family to the annual Pumpkin Float at Frog Pond featuring floating pumpkins, luminaries and fun family activities! Refreshments, music and child-focused activities will make this a spooktacular way to celebrate Halloween. This is a FREE event presented by Boston Parks and Recreation in partnership with The Skating Club of Boston.  Bring your carved 8-inch pumpkin to one of the drop-off areas alongside the pond. We will illuminate them and float them for you. Watch as the pond fills up with glowing pumpkins. Halloween costumes are encouraged!  This family friendly event happens on Sunday, October 23rd from 4:30pm-6:30pm.

St. Peter Academy Spooktacular Halloween Event:
Enjoy some good old fashioned family fun at the St. Peter Academy Spooktacular Halloween Event! Head to the Lithuanian Club – 368 West Broadway on Friday, October 28t from 6pm-8pm!   Bring the kids to this fun-filled event with food, crafts, contests, dancing and more!  $20 for family of four.  $5 for each additional person.

RISE of the Jack O’Lanterns:
Get in the Halloween spirit at RISE of the Jack O’Lanterns featuring over 5000 carved and lit pumpkins! With four dates to see this iconic fall event, RISE take place indoors at the Boston Seaport Hotel and World Trade Center, from October 27 – 30. This is a perfect family-friendly event featuring hand-carved illuminated jack o’lanterns creatively arranged along a scenic walking path, set to a musical score.  Ticket information can be found here! 

Halloween Costume Dance Party:
Get those dancing shoes ready and head to the South Boston VFW Post (7 Ellery Street) on Friday, October 28th from 8pm-12am.  DJ LeAnne “Skip” Boylan will be spinning the tunes.  Tickets are $20  Proceeds from ticket sales will benefit K’s Place – a transitional home for women.

District Howl:
The biggest Halloween Bash in the Seaport District is happening at District Hall – DISTRICT HOWL! There will be live music from Never in Vegas, Halloween treats,tricks and a $300 CASH PRIZE for the BEST COSTUME!  21+ with valid ID.  For tickets visit here!  $10

Halloween at the PC:
You don’t have to be Polish to enjoy this Halloween Party!  Head to the Polish American Club (82 Boston Street) and enjoy a night of costumes, live DJ, cash bar and a best costume prize! Tickets are just $5 and you can purchase them here!

Cornhole Costume Challenge at the BAC:
Have fun for a cause!  The Boston Athletic Club is hosting a Cornhole Costume Challenge On Saturday, October 29th – 100% of proceeds go to the Angel Fund to support their fight against ALS. There will be a DJ, 2 complimentary drinks for each participants, food, and lots of great prizes. Doors open at 12:30pm.  Games start a 1pm.  Tickets are $60 for teams of two if you pay online and $80 at the door.   You can also just be a spectator for $20!  You can register here!  

70’s Night at Loco:
Loco Taqueria and Oyster Bar is celebrating the decade of bell bottoms, disco, and women’s lib.  Relive the 1970’s on October 29th from 9pm-1am.  DJ Ryan Brown will be spinning all your 70’s favorites.  Wear your best 70’s duds and you might just win the costume contest!  No cover!

Costumes for a Cure:
Stephi’s in Southie is hosting a special Halloween fundraiser for Leukemia & Lymphoma Society on Friday, October 28th beginning at 8pm.  Tickets are $50 and include two complimentary cocktails made with Tito’s Vodka, appetizers, DJ and dancing and costume contest!  To purchase tickets visit here!  100% of the proceeds will got to the Leukemia & Lymphoma Society with Tito’s Vodka matching every dollar raised!

Halloween on the Harbor:
Who says you have to wait until the 31st for Halloween? Start the party on Friday, October 29th with the best bar crawl in the Seaport District, Halloween on the Harbor! Walk or ride in a decorated duck boat to various venues along the waterfront from 7-10 PM and then hit the after party at MJ O’Connor’s at the Westin Hotel. Tickets can be found here and proceeds benefit Friends of the Fort Point Channel. $10 must be 21+

Halloween Fun at Coppersmith:
Enjoy a Halloween Family Brunch and Costume Contest. Join Coppersmith on Saturday, October 29th for brunch and bring your best Halloween outfit and win big for a great 1st ($500), 2nd ($250) and 3rd ($100) prize for college planning. Also, first 50 families will have free pumpkin carving available and everyone can come in and try their luck bobbing for apples all while we have family inspired Halloween movies playing in the background. Come experience home style cooking with Chef Jason Heard and don’t forget to try our DIY Bloody Mary Bar.

Costumes and Cocktails at the Playwright:
Monsters and ghosts and witches on brooms,
You’re invited to party under the moon.
It’s Halloween time, so come get a fright
Dancing and drinking and music all night!
COME IN COSTUME FOR A CHANCE TO WIN PRIZES!
We’ll have a DJ, Halloween inspired cocktails and more! Spread the word!  The fun happens on Saturday, October 29th from 9pm-1am at the Playwright! 

Stats Halloween Bash:
Stats is hosting a special Halloween Party on Saturday, October 29th from 8pm-1am.  There will be prizes for best costumes!

Trick or Treating on Broadway:
Trick or treat!  Smell my feet!  Beware of little ghosts and goblins (and their parents) roaming the streets in search for Halloween candy.  East and West Broadway will be filled with trick or treaters onMonday, October 31st from 4pm-6pm picking up candy from local businesses and residences.  So be warned!  This event is free and is hosted by the members of the South Boston Chamber of Commerce.

Check back – we’ll be adding more exciting events weekly!

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About the Author

Maureen Dahill

Maureen Dahill is the editor of Caught in Southie and a lifelong resident of South Boston sometimes mistaken for a yuppie. Co-host of Caught Up, storyteller, lover of red wine and binge watching TV series. Mrs. Peter G. Follow her @MaureenCaught.