5.4 min readBy Published On: October 26th, 2023Categories: See and Do0 Comments on Weekend Picks – Halloween Weekend 2023

IT’S  HALLOWEENKEND!!! Need plans for a spooky weekend? We got you covered!

Southie Spooktacular Halloween Parade

Get decked out in your most Spooktacular costume and strut your stuff on Saturday, October 28th at 3pm at M Street Park. There will be Halloween music, free popcorn, a balloon artist, a photo booth, games, crafts and costume contests/prizes (for dogs, too!).  Decorate a mini pumpkin with a funny face, or try your hand at the potato sack race!  Bring a bag for trick or treating! Find a house with a balloon around the park and trick or treat. See you there!  Follow the event on Instagram for the latest!

Halloween Fest at the Lot

Halloween Fest at the Lot will be a family-friendly event on Saturday, Oct. 28th from 4-9pm. Kids are encouraged to come in costumes to carve pumpkins and participate in other Halloween activities. There will be food and refreshments from the Cannonball Cafe. Beer and wine will be provided for the adults. The event is free but you can reserve a spot here!

Halloween at Lincoln

Lincoln is hosting a Halloween party on Oct. 28th. They will have live music featuring DJ Stenny. Enjoy delicious food and drinks to celebrate the spooky day. Make your reservations here!

Halloween Party Cruise

Calling all witches and zombies for a Halloween party cruise through the Boston Harbor on Sat. Oct. 28th from 6:30 to 9:30pm. The event will have spooky cocktails, ghoulish grub, and a DJ. Make sure to bring your best witch or zombie costume for a contest! Get tickets here!

Halloween at Capo

Head on down to the Supper Club at Capo for a night of fun on October 28th at 8pm. There will be live music brought to you by It’s Ya Boy KR. Wear your best costume for a chance to win $500 CASH!! I suggest going as the ghost of the original door guy who greeted you in a suit. 

Halloween at Shamrock Pub

Spend your Saturday night at the Shamrock Pub. The event will be sponsored by Angry Orchard. They will have a costume contest, giveaways, tastings, and more! There will be live music by Evin O’Riordan. 

Dia De Los Muertos Halloween Fiesta

410 Lounge at Loco is having a Halloween Fiesta on Saturday, Oct. 28th at 9pm. The event will have live music by DJ Flynn Rink, drink specials, and a costume contest. Walk-ins are encouraged but you can also reserve a table by emailing [email protected]

Hunter’s Halloween Party

Hunter’s is getting in the Halloween spirt on Saturday night starting at 9pm. There will be live music from DJ Cam Wick. Make your reservation here!

Fat Baby Halloween

Fat Baby will be having Scary-oke on Friday, Oct. 27th. They will also be having a costume party on Saturday, Oct. 28th, with a DJ. There will be prizes and giveaways. Make your reservation here!

The Broadway Halloween Party

The Broadway is hosting a Halloween party on Saturday night at 9pm with costume contest.  Winner will receive a $100 gift card.

Prepare for Game Day at The Dirty Italian

The Dirty Italian now has appetizers and desserts for game-watching! Featuring everything from steak and cheese eggrolls, wing dings, mac and cheese bites and more, in addition to the Dirty Italians famous cheese cake brownie balls, pistachio almond cake, chocolate chip cannolis and more!

Sinful Halloween Soiree

Join Tall Ship for a Sinful Halloween Soiree on Saturday, Oct. 28th from 7-11pm. The spooky night will include food and drink, dancing, and a wicked good time. Come in your best costume! Get your tickets here!

Howlween Event at South Boston Dog Park

The South Boston Bark Park is having a  Howl-o-ween Doggie Costume Contest and Fundraising Event on Sat 10/28 from 11am-1pm. The Doggie Costume Contest judging will be at 12pm. There will be prizes, raffles, and pooch party favors. 

PKL Family Friendly Halloween Brunch Event

On Sunday from 12pm-4pm at PKL enjoy a family-friendly Halloween celebration featuring mini pumpkin decorating, a free kids pickleball court, Halloween movies in the lounge, plus a tattoo station, photo booth, corn hole, prizes and more! Costumes encouraged!  Plus games, live music and Bloody Mary flights for the adults!

Last Call For SoWa Open Market

Sunday is SoWa’s last day for the open market from 11-4pm. Artisans, craftspeople, designers, and local farmers gather in the SoWa Open market, and shop owners open their doors. They have live music and food trucks.

Irish Step Dance Lessons + Membership Drive

The South Boston Irish American Society is hosting Irish Dance Lessons at Seapoint (upstairs). The Woods School of Irish Dance will be leading the class on Sunday, Oct. 29th from 2-5pm. It is $10 at the door. There will be a cash bar and raffles. Plus, fill out an application and become a member of the Irish American Society! 

ICA Playdate-Spooky Shadows

Spooky Shadows is a family-friendly activity at the ICA on Saturday, Oct. 28th from 10-5pm. Create shadow puppets with Shadow play artist Lily Xie. The museum admission is free to families on Saturday! Reserve tickets here and use code PLAYDATE at checkout. 

Southie Costume Crawl

Put on your costume and bar crawl all over Southie on Saturday, Oct. 28th. Check in at Publico or Six West from 12-2pm. Once you receive your bracelet, you will have free access to all the bars featured on the crawl. The bars include Castle Island Brewery, Fresh Boston, Worden Hall, Telegraph Hill, Seapoint, Dot Tavern, Stats, Hunter’s, Broadway, The LOT on Dot, and Moonshine 152. Get tickets and find out more info here!

Layla’s Spooky Brunch

Layla’s is hosting a spooky brunch on Sunday, Oct. 29th from 10am-3pm. There will be a costume contest and frightfully delicious specials from the kitchen and bar. Make your reservations here!

New Art Exhibition at the Gallery at  249 A Street 

The Gallery at 249 A Street announces the opening of its latest exhibition.”VIDEO+PAINT · NEW WORK · BEBE BEARD + STEVEN MULLER.” The gallery is free and open to all by appointment. To arrange to see the show, please email [email protected]. The Gallery at 249 A Street is supported by a grant from the South Boston Community Development Foundation.


Patriots Vs. Dolphins Oct. 29th at 1pm. 

Bruins Vs. Red Wings Oct. 28th at 7pm. 

Celtics Vs. Heat Oct. 27th at 7:30pm.

Here are 12 spots to watch the game in the neighborhood! 

Check back! This list may be updated.


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