Weekend Picks – June 26th
The Layover is Back for a New Season
Picture yourself sipping a frozen drink surrounded by lush greenery, with amazing views of the city and a gentle summer breeze in the air! This exact scenario is the backdrop of Eastie’s tropical rooftop destination, The Layover! This ultimate urban escape sits atop Cunard Tavern at 24 Orleans Street and is back open for the season! The Layover’s walk-up window bar offers craft beer, wine by the glass, specialty cocktails, and a rooftop dining menu. Enjoy refreshing tiki cocktails crafted with rum and fresh fruit juices alongside innovative twists like the Mai Tai and Painkiller. Pair your drink with quick bites infused with island ingredients and global influences!
Pup Cup Social at Mary Ellen Welch Greenway
Pups will enjoy a tasty treat while socializing with other dogs! Take home a Greenway photo memento and have some fun! Takes place on Saturday, June 27th from 10am-12pm at the Greenway.
Anchor + Aligned: Pilates for a Cause at The Tall Ship
Enjoy an elevated wellness experience bringing together movement, community, and giving back to the United Ostomy Associations of America (UOAA) on Jun 27, 2026, 9:30 AM – 1:00 PM at the Tall Ship. Get more details, including tickets, here.
✨ WHAT TO EXPECT:
• High energy Pilates experience led by Monika Benson
• Curated wellness & lifestyle vendors
• Drinks & Small Bites
• Attendee goodie bags
• Raffles & giveaways
•Complimentary Cold Plunge provided by Plunge Boston
‘Tis the Season for Slush King
With warmer temps and longer days, the summer season is perfect for enjoying ice-cold treats! Enter Slush King, offering everything from homemade slush to ice cream sandwiches! Slush King has been around since 1965, operating push carts at Boston Common and at festivals throughout New England. In 2020, Slush King opened a window at 211 Bennington Street, where you can order your favorite ice cream treats every day from 1pm-10pm.
Sip & Sculpt Pottery on the Patio Workshop at Downeast
Sip, sculpt, and unwind! Join our pottery workshop to create unique handmade gifts or décor while enjoying a fun, relaxing experience. Unplug, unwind, and make something by hand at our feel-good pottery night, no experience needed. Whether you come for the joy of making, community, or a mindful tech-free moment, this guided clay workshop is all about making something fun while you sip and socialize. You’ll learn the pottery basics, and leave with a one-of-a-kind piece (or two) you built by hand as well as a deeper sense of calm. Takes place on Sunday, June 28th at 1pm at Downeast Cider. Get your tickets here.
FIFA World Cup Fever – East Boston Community Watch Party on Saturday
Mayor Michelle Wu recently announced that the City of Boston will host six community watch parties for residents, families, and visitors this summer. Together with the FIFA Fan Festival hosted by Boston 26, these neighborhood celebrations will bring the excitement, energy, and spirit of the World Cup directly into communities across Boston. From Dorchester to East Boston, Roxbury to Charlestown, neighborhoods across the city are already buzzing with anticipation as Boston prepares to host seven FIFA World Cup matches this summer. Mayor Wu’s community watch parties are one way to help ensure that the excitement, celebration, and opportunity associated with this summer’s historic events extend into every neighborhood, giving residents the chance to celebrate the tournament in their own way. Watch the Colombia vs. Portugal match on Saturday, June 27th at 7:30pm at East Boston Memorial Stadium.
Dock + Dine at Reel House
Pull up, tie up, Dock & Dine! Cruise into ReelHouse East Boston all summer long for dinner, drinks, and skyline views right from the harbor.
Last Call for the June exhibition at AWG: On Motherhood in Times Like These
This June, multidisciplinary artist Kristen Freitas presents On Motherhood in Times Like These, a solo exhibition at the Atlantic Works Gallery exploring the layered realities of motherhood through themes of family, heritage, resilience, and resistance. Get all the details here
SPORTS!
Red Sox vs. Yankees – Friday, June 26th at 7:10pm, Saturday, June 27th at 1:10pm and Sunday, June 28th at 7:20pm.
World Cup Matches – check out the schedule here.
Here are 7 Places to Watch in the Neighborhood!
More FIFA World Cup Fever
The FIFA World Cup is coming to Boston (well…Foxboro), and whether you’re lucky enough to have tickets to a match or plan on watching here in the neighborhood, we’ve got you covered. From where to watch the games and can’t-miss fan festivals to special events, watch parties, transportation updates, and street closures, this guide has everything you need to make the most of one of the biggest sporting events in the world. Get ready, Boston—it’s about to get nuts! Get all the details here.
Check back as this list may be updated!
Have a fun weekend! Thank you to our Caught in Eastie readers and Neighborhood Partners for supporting our local journalism efforts!
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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