4.8 min readBy Published On: December 15th, 2022Categories: See and Do0 Comments on Weekend Picks – December 16th

Holiday Drinks to Get you in the Spirit

Peppermint, hot chocolate, egg nog, and vanilla! We don’t know about you, but these delicious flavors get us in the holiday spirit!  And here are some holiday-inspired drinks we’re excited to try in the neighborhood!  Check them out here! 

Ho Ho Hoedown at PKL

On Friday from 8pm-11pm, PKL is hosting a Ho Ho Hoedown with live country music featuring Lexi James + Wildheart.  Line dancing lessons from 603 Line Dance.

Wrap Stars at The Broadway

The Broadway will be offering complimentary gift wrapping from 3-6 pm on Friday, December 16th. Guests are welcome to bring their gifts to be wrapped while enjoying lunch or dinner. Broadway staff will wrap their gifts for guests for NO charge. Volunteers are welcome to join!

Pop-Up Coffee Shop on West Broadway

The Nitro Bar will be popping up at 75 West Broadway (inside) on Sunday from 8am-1pm. We hear the coffee is delicious!

Holiday Entertaining at Home – Made Easy!

We’ve got the scoop on where to get delicious meals, side dishes, and desserts for all your holiday entertaining!  Check out the roundup here! 

Eat, Drink + Be Merry at Roza Lyons

A holiday fundraiser will take place on Saturday at 1pm at Roza Lyons to benefit the South Boston Neighborhood House! Kindly bring an unwrapped toy to donate or you can make a cash/check donation at the door!

Welcome to the Neighborhood, Shy Bird

In the ever-changing landscapes of restaurants in the neighborhood, there’s a new one now open!  Shy Bird – has opened its doors in the new Iron Works building.  Shy Bird’s menu features half and whole chicken, fried chicken sandwiches, burgers, pretzels, salads, burgers, beer, wine, cider, and cocktails. Use the code: CAUGHTINSOUTHIE15 for 15% off delivery/takeout!

Love Child Tastings

Love Child will be tasting Italian wines with Colleen from Dolce Vita Wines on Friday from 5-7.  On Saturday, it’s Day Drinking with Faux Pas canned cocktails!

Nauti or Nice Party

Nautilus Pier 4 is celebrating the season with their Nauti or Nice party on Saturday, December 17th. The fun begins at 8:00pm and will feature a champagne bar, ice luge, inflatable polar bears, drink specials, and more. DJ Ryan Brown will be playing so wear your dancing shoes. Prizes for those in their nautiest or nicest costumes/sweaters! 

Fresh Christmas Trees Delivered to Your Door

Do you still need a Christmas tree? Christmas Tree For Me will deliver a fresh tree to your door with just a click of the mouse! Experience the ultimate Christmas convenience: prompt tree delivery with the option of setup and removal. You simply select your Fraser or Balsam Fir online and they’ll deliver it to you!

Ugly Sweater Party at Loco

Wear your best…or worst…ugly sweater and head to Loco on Sunday from 2pm-8pm.  Enjoy food + drink specials, DJ Ansounds from 3pm-8pm, Patriots game at 4pm.  $250 Loco gift card for Best Sweater!

Girl Scout Cookies Pop-Up

Thin Mints, Peanut Butter Patties, Caramel Delights – we love them all!  On Sunday, the South Boston Girl Scouts will be selling cookies in front of Deja Brew from 10am-2pm.

Into the Soul Solstice

Flow, restore, sounds + Reiki at East Side Yoga and Fitness on Sunday! 

Karaoke + Carols at Telegraph Hill

On Sunday night, Telegraph Hill Kitchen & Bar is getting in the holiday spirit with “Karaoke & Carols.” Whether you’re “Rockin’ Around the Christmas Tree” or channeling your inner Mariah to bring the people what they want (which obviously is “All I Want For Christmas Is You” for the seven thousandth time this season), bust out those ugly sweaters and make fellow bargoers envious of your merry octaves. There will be specialty cocktails too! Fun starts at 7pm. 

Betty The Yeti Bar Crawl

Grab a special Betty-inspired cocktail (or mocktail!) for a great cause on the Betty the Yeti Bar Crawl. Pick up a crawl card from participating locations, get a stamp at each stop, and earn a free Betty beanie. For every Betty cocktail sold, Seaport will donate $1 to 826 Boston, a local youth literacy organization. Tag @seaportbos to share your sips. Participating Locations include:

– The Envoy

– Scorpion Bar

– Kings

– Tuscan Kitchen

– Yotel

– Gather

Last Minute Shopping in the Neighborhood

Forget the mall! Shop local! Shop Southie! Pick up last-minute gifts and stocking stuffers or treat yourself to something nice! You’ll be supporting local businesses. So really, it’s a win/win! Check out our roundup here! 

Live Music Roundup

Hunter’s is featuring Ryan + Annie Cheevers on Friday from 4pm-7pm. On Saturday, Ryan Flynn from 3pm-6pm and Sunday It’s Ya Boy KR 2 from 2pm-5pm and Matty Sheehan 9pm-12am.

Loco will have DJ Alex Walker on Friday in the Lounge starting at 9pm. On Saturday it’s Kim Cherry from 1pm-4pm followed by DJ Colin Tonge at 9pm. On Sunday – Loco will host an Ugly Sweater on Sunday!

Lincoln will host Legends of Summer Band on Sunday from 6pm-9pm

Capo is featuring Copilot on Friday from 8pm-11pm, on Saturday it’s Pat Dowling from 1pm-4pm, Cold Wayne Band 7pm-10pm on Sunday enjoy Sinatra Sunday with Rich Dimare and the Ron Poster Trio at 6pm.

PKL will feature Legends of Summer Band on Saturday from 8pm-11pm.


The Celtics play the Magic on Friday at 7:30pm and Sunday at 3pm. Bruins face off against the Blue Jackets on Saturday at 1pm.  World Cup Finals – France vs. Argentina on Sunday at 10am!  The Patriots face the Raiders on Sunday at 4pm.  Here are 10 Places to Watch the Game! 

Check back as this list may be updated.

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