It’s so important to support our small business community! Here are some festive events and pop-ups happening in the neighborhood! Check back, as this list will be updated!
Get Ready for a Festive Holiday Stoop Stroll in Southie!
Purchase your tickets here!
Mark your calendars and dust off your holiday attire! On Sunday, December 22nd, from 4pm-7pm, Caught in Southie is hosting a Caught in Southie Holiday Stoop Decorating Competition + Festive Stroll, and you’re invited to join the merriment! This one-of-a-kind event is your chance to explore the neighborhood, admire some seriously impressive holiday decor, and enjoy the warm hospitality of participating homes. Each stop will offer festive refreshments and entertainment to keep the holiday vibes strong.
Here’s how it works: snag your $10 ticket to access all the holiday magic. Not only will you be treated to a joyful evening of twinkling lights and holiday cheer, but your ticket purchase will directly benefit the South Boston Neighborhood House. That’s right—this event is a win/win!
At least 8 South Boston homes are participating in this stoop stroll and competition. A final map will be published 48 hours before the event! Pick up your “festive accessory” that will act as your ticket for this neighborhood event on the Saturday before a the CIS headquarters at 136 M Street. Any questions, email [email protected]
4th Annual Ship Lighting at Martin’s Park
Get in the holiday spirit at Martin’s Park for the Annual Ship Lighting! The event will be held on Saturday November 30th from 4 to 6pm. The Park’s wooden playship is the centerpiece of the space and will be transformed into a beautiful holiday display when the ship, surrounding fencing, and pedestrian bridge are illuminated with over 7,600 feet of white and blue LED lights. Many A-List local celebrities will be there including Wally and Tessie the Green Monsters and Betti the Yetti. And a special appearance from Santa and The Grinch!! Stop by and spread some Holiday Cheer! Get all the details here!
Petula’s Neighborhood Party
All are invited to Petula’s Neighborhood Holiday Party on Sunday December 1st from 2 to 5pm. There will be complimentary photos with Santa, face painting, festive tunes. And most importantly, festive drinks and cocktails! All are encouraged to bring school supplies or $10 to go to a local Southie school! Give back to the neighborhood and kick off December right!
Hunter’s Holiday Tree Lighting
Join Hunter’s for their 2nd Annual Tree Lighting on Wednesday December 4th at 8pm. Enjoy awesome music by It’s Ya Boy KR. There will be festive drinks and specials. The cozy cabin will be decked out for the holiday season! Make your reservation here!
Lincoln x Market Floral Studio Holiday Wreath Workshop
Grab your friends and head over to Lincoln to create a Holiday masterpiece. Market Floral will be leading a Wreath Workshop on Monday December 2nd at 7pm. The class is $75 and includes step by step instruction to create a beautiful holiday wreath with fresh juniper berries, incense cedar, eucalyptus, pinecones and other fun accessories. Secure your tickets now!
Merry Moakley
Boston Harbor Now is excited to co-host Merry Moakley for its third year, thanks to the support of the City of Boston Parks and Recreation Department, South Boston en Acción, South Boston Neighborhood House, the Boston Family Engagement Network, and Volo. A family-friendly evening of festive outdoor fun featuring food, crafts, live music, free books, photos, games, and more! Thursday, December 12th, from 3:30 pm – 5:30 pm South Boston Neighborhood House Preschool Parking Lot, 1187 Columbia Road, Boston, MA For more information about Merry Moakley, Moakley Park, and a complete schedule of winter activities happening on the Boston Harbor waterfront, visit here.
Breakfast with Santa at Publico
Santa is coming to town!! Santa will be at Publico December 7th,14th, and 21st for a family friendly breakfast! There will be a full breakfast buffet and festive holiday cocktails for the adults. Secure your spot now!
The Winter Market at Publico
Step inside a winter wonderland at Publico! They have created an enchanting 360° installation inside Publico’s Garden! This wonderland installation features lush winter greenery, a jaw-dropping 16-foot dazzling lit Christmas tree, twinkling holiday lights, and festive and fun ‘holiday market’ inspired drinks and snacks! It is the perfect way to get into the holiday spirit. Make your reservation here!
South Boston Catholic Academy Jingle Bell Run
The 15th Annual Jingle Bell Run will be held Saturday, December 7th at 10 am. There will be 2 youth races at 9am, featuring a 100 meter dash for kids 9 and under and a ½ mile race for kids 14 and under. The main event is a 5km run along the beaches and around castle island. There will be refreshments, food, entertainment, and awards after the race. Sign up and get more info here!
Ugly Sweater Karaoke at Small Victories
Grab your ugliest holiday sweater and head over to Small Victories on December 4th at 8pm. Join in karaoke while sporting your ugliest Christmas sweater! The winner of best performance and best sweater gets $50! Mark your calendars and follow them on instagram for updates!
Loco’s Holiday Sip & Shop
Loco will be hosting a Sip & Shop in the 410 lounge on Sunday December 15th from 1-4pm. There will be over 12 local stores participating. It is a great way to get some last minute gift shopping done and enjoy a margarita or two! Caught in Southie will be there with some Southie merch and vintage clothing and accessories – two of our favorite things.
Kids Cookie Decorating Night at The Broadway
It is time for The Broadway’s Annual Cookie Decorating Night! They will have two dates due to their popular demand! They will be held on December 4th and December 18th from 5 to 7pm. Each ticket is $10 and includes freshly baked cookies, decorating supplies, and a festive to-go box (No ticket needed for parents and guardians). Get your tickets before they are gone!
Deck the Bottles at The Playwright
Decorate your own wine bottle at The Playwright! The ticket includes a wine bottle to personalize, decorating supplies, a complimentary drink, charcuterie spread, and best of all house sangria to fill your finished bottle! A perfect pairing for your next holiday gathering! Get your tickets here!
Holiday Wreath Workshop at Loco
Stop by for a Sunday fun-day at Loco on December 8th at 1pm ! Jump into the holiday spirit and come create your own winter greenery wreath- no previous experience required! Owner and lead designer Kayla Ciavarra of BUDS Floral Design will guide you in a step-by-step instructed class to create a hand tied greenery wreath to bring home for the holidays. Decor items such as ornaments, bows + other decorative items will also be provided to make your wreath truly unique. Loco’s full brunch menu will be available to enjoy during class! Get your tickets here!
Capo Sip & Shop
Get ready to sip, shop, and be merry at Capo! Their Sip & Shop will be held on Saturday, December 7th, 2024 from 11am to 3pm. There will be 20+ local vendors, delicious food and drink, and a visit from Santa!! It is free so stop by for a festive event.
Santa Social Run by Castle Island Track Club x The Broadway
Join the Castle Island Track Club for a holiday run around Southie, on December 14th at 10am. Wear some festive garb and meet the group at The Broadway. The run is a 5K and will end at The Broadway for a celebration at their back bar. RSVP on strava. The event is free, but donations to Good Sports are encouraged. Get all the details on their instagram!
Capo Christmas Karaoke
The best way to spread Christmas cheer is singing loud for all to hear! Head over to Capo Basement for Christmas Karaoke on December 19th from 8pm to 1am. Sing the night away while enjoying great food and drinks. Reserve your spot here!
Fresh Festivus
Join Fresh for their Festivus on Wednesday, December 18th at 6pm. Come wearing a festive outfit like an ugly Christmas sweater or festive PJs. Chef Peter will be preparing a delicious holiday meal with a wine pairing. The tickets are $115 and include the meal and wine. Get all the details and tickets here!
Hunter’s 1st Live Christmas Sing-Along
As if their awesome decorations weren’t enough to get you into the holiday spirit, Hunter’s will be hosting a Christmas Sing-Along! The Sing-along will be on Saturday December 14th from 1 to 3pm and Wednesday December 18th from 7 to 9pm. Stop by to belt out the songs or just enjoy the music! Make your reservation here!
3rd Annual Cisco Stroll
The Cisco Stroll will take place on Saturday December 14th from 12-4pm. There will be exclusive scarf giveaways, live music, holiday decor contest, and cisco brews. For every pint of Cisco sold, $1 will be donated to the South Boston Neighborhood House. The participating bars are Loco, Lincoln, Layla’s, Publico, Fresh, Roza Lyons, Hunters, The Playwright, and The Broadway. Stop by your favorite bar for a Cisco and a good time. Get all the details here!
The Broadway Holiday Showcase
Small Local Businesses will be taking over The Broadway, on December 11th from 6 to 9pm. Sip and shop your way around the booths. It is the perfect place to buy Christmas gifts or treat yourself!
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