Weekend Picks – LDW 2026

Slow Mornings at Eagle Hill Café
Start your morning at Eagle Hill Café (65 Meridian St.) with fresh coffee, breakfast sandwiches, and homemade pastries. Open daily, it’s the perfect neighborhood stop for breakfast or an afternoon pick-me-up.
Labor Day White Party at The Tall Ship
End summer with a party on the waterfront! The Tall Ship in East Boston is hosting its annual Labor Day White Party on Monday, September 7th. Wear your best white, enjoy a live DJ, and soak up the last unofficial weekend of summer. This is a ticketed event. Purchase yours here. Plus, there will be live music on Friday, Saturday, and Sunday! Check out the lineup here.
Visit Santarpio’s
An East Boston institution since 1903, famous for thin-crust pizza and charcoal-grilled lamb skewers and sausage. Cash only. 111 Chelsea St, East Boston. More here.
Hop on a ferry for a fun summer adventure
Looking for a fun activity around the neighborhoods? Check out the boat shuttle service that connects you from ReelHouse East Boston to Charlestown’s waterfront and the Seaport. Boston Launch Company runs their boat shuttle service daily from 11 am until 11 pm, making stops at Pier 6, Reel House East Boston, The Tall Ship, and ReelHouse Oyster Bar in the Seaport. The service costs $4 a ticket but is free during Sumner Tunnel closures. It is such a fun, easy, and convenient way to get around the city! Get all the fun details here!
Drinks + Apps on the Roof
Enjoy some tropical summery cocktails and appetizers on the Layover’s Rooftop Bar!
Take a sunrise or sunset kayak tour
What better way to start or end your day than with a guided sunrise or sunset kayak tour of Boston Harbor? The Piers Park Sailing Center offers guided sunrise and sunset tours this weekend! It’s a great way to explore the city from the ocean! You can book the morning session here and the evening one here! Kayaking at Piers Park helps support its public access, youth, and adaptive programs. They are also open for regular public kayaking; you can reserve a time to kayak the Piers Park Cove by booking here.
Free Museum Admission at ICA on Labor Day
In honor of Labor Day the ICA is offering FREE admission for all on Monday, September 7. Tickets are required and will be available to reserve beginning on Sunday, September 6 at 10 AM. Timed tickets are required to board the ICA Water Shuttle boats and will be available on Sunday, September 6 at 10 AM as well. Admission to Lucy Raven: Rounds at the Watershed in East Boston is always FREE—tickets are not required for entrance. Water Shuttle tickets include general admission to the ICA in the Seaport. Reserve your ticket here!
Sculpt at Cisco Fenway
Join Cisco Fenway for Yoga Sculpt at Cisco Fenway on Sunday, September 6th at 10:30am, where movement meets community! Dive into a summer atmosphere and connect with fellow yogis and fitness enthusiasts as you flow through a workout led by local Fenway Instructor GABRIEL DIAZ. Whether you’re a seasoned yogi, a beginner or just curious to find out what your body is capable of, this is the perfect place to experience amazing music, like-minded individuals, and a great burn! Don’t miss out on this unique event – see you at Cisco Fenway! Reserve your spot here!
Yacht Rock Sundays at Park City
The sweet sounds of Yacht Rock will be taking over Park City on Sunday, August 6th. The Blue Light Bandits will be performing from 5-8pm. The drinks will be flowing! Stop by for an awesome time! Nautical outfits encouraged!
SPORTS!
Red Sox vs. Orioles – Friday, September 4th at 7:05pm, Saturday, September 5th at 7:05pm, and Sunday, September 6th at 1:35pm.
US Open Matches – Check out the schedule here.
Here are 7 Places to Watch in the Neighborhood!
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!

Hi! I’m Carina! I’m a junior at Northeastern University doing my Co-op at Caught in Southie; I’m very excited to be here! My favorite Boston spots are Chez Vous Roller Rink and Show Malatang- you can find me there most weekends! I love hanging out with my friends, reading, pickles, hockey, roller blading, and anything to do with music. Reach me at [email protected] to talk Boston!


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