Now Open – The Blue Caboose

The Blue Caboose, the iconic historic blue train car on the Greenway, is officially open for the season! The ice cream and coffee stand announced the news on an Instagram story on Tuesday.  The menu will feature coffee, tea, and ice cream! Get all the details here! 

Rosé all weekend at The Tall Ship

Enjoy Rosé by the Sea June 4–7, 90+ Cellars is taking over The Tall Ship in East Boston for the first-ever 90+ Cellars Rosé Weekend!
All weekend, the wine truck is pouring 90+ rosés right on the East Boston waterfront 🍷 Saturday, 10 AM, a high-energy sculpt + barre class with @seaavision and @barregroove founder Alanna Perry, followed by a 90+ Rosé Social Hour and Seaav Wellness Lounge on the water 🧘🏼‍♀️ Saturday evening, June 6…the main event! A full takeover of the Tall Ship for an epic rosé sunset party. Grab your tickets QUICK, this one will sell out! 🌅 Get your tickets here!

A new 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. Opening Reception is Saturday, June 6th from 2pm-6pm. Get all the details here. 

Let’s Get Movin’ 5K

Neighbor Health hosts its annual Let’s Get Movin’ 5K run for a fitness fundraiser in support of its many programs and initiatives that support our community. Registration is required and Bib pick up time for runners begins at 8:30 am. Donations are welcome as well.

Saturday, June 6, 2026
10:00 am
Memorial Park
143 Porter Street, East Boston
runsignup.com/lgm5k

Boston Chilling Music Festival at the Lawn on D

The Lawn on D officially reopens this Saturday for the 2026 season with a fresh new look and a brand-new name: The Grove. The popular outdoor gathering spot has been transformed into an urban botanical oasis complete with lush greenery, gathering spaces, and one of the largest LED screens in Greater Boston—perfect for World Cup watch parties, outdoor movies, and more.  To celebrate opening day, Harpoon Brewery is hosting the inaugural Boston Chilling Music Festival, a FREE afternoon of live music featuring Lily Fitts, Ali McGuirk, Daundry, Toledo, and Lightfoot Beats. Local favorite Reporter Matt will be on hand as emcee for the day. The festivities kick off at 1 p.m. and continue through sundown.

Sunset Sip Club by Love Child x Cisco Brewers Seaport

Looking for a relaxing way to wrap up the weekend? Cisco Brewers Seaport x Love Child are hosting a golden-hour floral arranging class that combines seasonal blooms, a complimentary glass of wine, and plenty of summer vibes on a Sunday evening. The first event takes place on Sunday, June 7th at 5pm, after class, attendees are welcome to stick around, enjoy the reserved space, and put the finishing touches on their arrangements until 8 p.m. Get your tickets here!

HB Outdoor Sculpt at Park City with Ritual Wellness

HB is teaming up with @ritual.wellness for a summer series, bringing HB Outdoor SCULPT to Park City every Saturday at 10am. Post workout recovery with@sweathouz
Your ticket includes access to the after-class wellness social:
🎧 Live DJ
🥤 Complimentary drink ticket + free coffee
🧊 Cold plunges + recovery zone
🛍️ Wellness pop-ups

Use the code CAUGHTINSOUTHIE for 20% off all Park City event tickets all season long for any non-run club ticket.

SPORTS!

Red Sox vs. Twins – Friday, May 22nd at 7:15 pm, Saturday, May 23rd at 4:15pm and Sunday, May 24th at 1:35pm.

NBA Playoffs – schedule here

NHL Playoffs – schedule here

Here are  7 Places to Watch in the Neighborhood! 

Check back as this list may be updated!