Weekend Picks – November 21st

East Boston Taco Trail Starts Now
This fall, Taste of Eastie is rolling out the brand-new East Boston Taco Trail—a cultural and culinary adventure that highlights the neighborhood’s incredible Mexican taquerías, Salvadoran kitchens, and Colombian grills. So, what’s the Taco Trail all about? Think of it as your “passport to flavor”—a guided way to explore Eastie’s authentic taquerías, hidden gems, and local spots serving up everything from street-style tacos to lively bar bites. It’s the perfect excuse to gather your friends and eat your way through the neighborhood. November 15th – February 28th You can learn more here!
East Boston Jeopardy
Come drink beer, play Jeopardy! and test your knowledge about Eastie while supporting families in need through the EB Crisis Response Fund. this fun neighborhood event has been organized by Eastie Gals and takes place on Saturday, November 22nd at 6:30pm at Democracy Brewing. Get your tickets here!
Salesian Boys & Girls Club 19th Annual Pasta Dinner
Enjoy A NIGHT OF FRIENDSHIP, FOOD & FUN on Friday, November 21, 2025, from 6:00 p.m. to 8:00 p.m. Tickets $10 Per Person. Delicious Food Provided by Sammy Carlo’s Delicatessen & Muffin Town. Many Raffle Prizes!! & Gift Baskets!!
Do Portugal Circus is in town!
Get ready, Eastie — the Do Portugal Circus is rolling back into town from November 7 through December 7, bringing a full month of high-flying acrobatics, dazzling artistry, and family-friendly fun! Expect breathtaking acts from the Portugal family themselves — including Carlos Portugal Jr. with his amazing juggling, Ivan Portugal on the Washington Trapeze, The Flying Portugals on the Flying Trapeze, and Eddy Portugal with gravity-defying hand balancing. Each performance is packed with color, energy, and heart — and best of all, it’s completely animal-free. Affordable and available daily — visit doportugalcircus.com for the full schedule.
Comfort Food at Cunard Tavern
Chicken Pot Pie season is officially at Cunard Tavern 🙌 Flaky puff pastry, creamy filling, and all the comfort you need! Try it this weekend!
Tarot + Chocolate
Join Heronkind for a tarot reading at @petrovachocolates at its North End location on Saturday, November 22 from 1-4PM! “In our tarot reading, we’ll ask Spirit for a message of guidance and support for your life right now. My readings are gentle, fun and inclusive. All cards offer gifts and healing! My hope is always that you’ll leave our session feeling inspired, uplifted, and empowered.” Sounds like fun! Book your appointment here!
La Cocina VROCC Opens this Week
La Cocina VROCC, a restaurant and community kitchen, is now open to the public. The chef and the team of young Latino entrepreneurs is proud to bring you the authentic flavor of Latin America at the corner of Maverick Street and Jeffries St. in East Boston. La Cocina VROCC is located at 389 Maverick St.
Celebrate National Espresso Day at The Well Coffee House
Celebrate National Espresso Day on November 23 with a visit to The Well Coffee House in East Boston. Known for its expertly crafted espressos and warm community atmosphere, The Well is the perfect spot to indulge in a frothy, perfectly balanced coffee treat. Whether you’re a espresso lover or simply looking for a cozy place to unwind, The Well Coffee House offers a welcoming vibe and delicious brews to mark the occasion. Check out their menu here!
Sacred Heart Parish Christmas Fair
The Sacred Heart Parish Christmas Fair will be held on Saturday, November 22 from 10-4pm. All are welcome to join this fun annual event. The fun kicks off at 10:00 am with a free Pancake Breakfast with Santa from 10-11:30AM. The much-talked-about food station opens at noon with delicious Italian and Spanish foods. And get an early start on your holiday shopping with vendors like jewelry, soap, children’s book author, crochet items, beaded pens, holiday gifts, and more! Plus a baked sale and raffles!
Prepare for Thanksgiving
Get your stretchy pants ready. It’s almost Thanksgiving! We’ve rounded up ways to help you prepare for Thanksgiving. Check out our guide here!
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.


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