Weekend Picks – May 30th

The Layover kicks off a new season on May 31st
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 opening this week. 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! The Rooftop season officially kicks off on Saturday, May 31st at 12:30pm with tropical cocktails and outdoor grilling! Think the best of summer flavors and big Eastie energy! This epic afternoon will feature James Beard Award-winning Chef Tony Messina, back in the neighborhood and ready to light up the coals! The party starts on the roof with tropical cocktails and snacks, then head downstairs for a curated summer feast including a grilled half lobster for every guest and other surprises! You can purchase your tickets here!
Dalton & The Sheriffs at Tall Ship
Celebrating an Anniversary, Dalton & The Sheriffs will be performing on Sunday, June 1st at 3pm. The show will have 3 acts and is guaranteed to be an awesome time! Get your tickets here!
It’s Lobster Roll Season at EBO Grocery!
Okay, so the weather this Memorial Day Weekend might not be giving “beach day,” but this news could brighten your mood. EBO + Co Grocery announced on Instagram that their legendary Lobster Roll Kits are back for the season! Each kit includes one pound of fresh Maine lobster meat (knuckle & claw) and a pack of Martins Potato Rolls and makes six lobster rolls. “Ain’t nowhere else you’ll be getting six lobster rolls for $75!” Truth! Pick one up this week– it pairs perfectly with a bottle of rosé!
Paddle all Summer
Piers Park Sailing has a new kayak pass that will have you paddling all summer long! Get moving on the ocean. You can learn more here!
Live Music at the ReelHouse
Sunday Funday! Enjoy a cocktail and an appetizer while you listen to live music on Sunday, May 4th from 2pm-6pm!
East Boston Family Bike Ride
“Family Bike Ride” a group whose mission is to highlight fun and safe infrastructure in the Boston area, one ride at a time, is taking it to Eastie! A group of riders will take the ferry from Boston then tour the Greenway on bike! Eastie riders are welcome to join. Meet at Piers Park Sunday, June 1st between 12 -12:30PM. Or you may join in at any point along the Greenway.
Celebrate National Burger Day in the Neighborhood
It’s National Burger Day! Whether you like it with the works or just a little ketchup, today is your perfect excuse to eat one! We are sharing our picks for some of the best burgers in the neighborhood!
Learn more about the Eastie Fruit Tree Project
East Boston Main Streets has partnered with TREE Eastie to launch the Eastie Fruit Tree Project, with support from GrowBoston. Come be a part of this growing movement! First event is May 31st – you can learn more here!
Sticky Buns Sunday
Enjoy freshly baked sticky buns from Cafe Iterum on Sundays! Pairs perfectly with their delicious coffee!
Patio Season in Eastie
Patio Season is here…well, if the weather cooperates! If we get lucky enough to see a sunny weekend day, check out all the patios in the neighborhood! Drinks taste even better in the sunshine! Check out our guide to get all the scoop!
SPORTS!
Red Sox vs. Braves– Friday, May 30th at 7:10pm, Saturday, May 31st at 4:10pm, Sunday, June 1st at 1:35pm
Here are 7 Places to Watch in the Neighborhood!
Check back as this list may be updated!
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.


5 Things You Should Know This Week – February 9th
A Guide to Celebrating the Lunar New Year 2026
Weekend Picks – February 6th