Weekend Picks – July 17th
Eastie Week Returns
East Boston’s annual celebration of community, culture, music, arts, and waterfront pride is returning this summer bigger than ever before. Now in its 13th year, Eastie Weeks 2026 will be the longest and most expansive celebration in the event’s history running from July 12 to 29. Led by East Boston community organizations and residents and supported by Boston Harbor Now, the celebration brings together artists, musicians, businesses, cultural institutions, and neighbors for two+ weeks of events that showcase the people, places, and partnerships that make East Boston unique. Get all the details here
Cartoons + Coffee on the Greenway
Nostalgic Saturday morning cartoons complete with cereal and milk on –Bremen Street Park.
B/Spoke class on deck of the Tall Ship
Join B/Spoke for Summer On Deck — the outdoor class series in the city! Tall Ship classes take place at 1 E Pier Dr, Boston, MA. Bring your mat and water and get ready to move outside. Book with the Summer on Deck $20 drop-in or existing credit/membership. You can book your spot here.
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!
World Cup Finals at The Grove
Looking for the perfect spot to watch the World Cup Finals!?! The Grove has everything from giant screens, awesome food and drink, and an incredible atmosphere. There will also be live music on both Saturday and Sunday! Plus, brand new this season, you can reserve your own private cabanas or lounges for groups ranging from four to 28 people. These come with skip-the-line access and dedicated service for all your food and drinks! Book your spot via here!
Get some ice cream in the neighborhood
When the summer sun is shining bright, there’s nothing quite like indulging in a refreshing ice-cold treat to beat the heat. In East Boston, you’ll find a delightful array of frozen dessert spots that cater to every palate and preference. From exotic flavors to unique combinations, here are the best places to savor ice cream and icy delights in this vibrant neighborhood. Check out our roundup here!
EBO+ Co Grocery Wine Tasting
On Friday, take part in the inaugural Basement Tastings series at EBO + Co Grocery from 6-8pm. Tasting wines from Massachusetts plus, snacks, vibes + good music
Yacht Rock Sundays at Park City
The sweet sounds of Yacht Rock will be taking over Park City on Sunday, July 19th. The Blue Light Bandits will be performing from 5-8pm. The drinks will be flowing! Stop by for an awesome time! Nautical outfits encouraged… by me, haha.
Fun on the Water
From sailing lessons to SUP, our neighborhoods have lots of ways to spend the day on the water! Eastie has Piers Park Sailing Center. Charlestown has Courageous Sailing. UMASS Boston in Dorchester offers waterfront fun, including kayaking, paddleboarding, and sailing. This service is available to UMB students, community members, and the public with the appropriate pass. You can learn more here. Southie has the Harry McDonough Sailing Center for kids plus Sup Yo Adventures offers Stand Up Paddle sunset paddles and yoga classes during the week on the Fort Point Channel. You can get all the fun details here.
Rent a shACK at Cisco
Cisco is the perfect weekend hangout, and their new shACKS make it even better! Skip the line, claim your spot, cold beers within reach & no “where are you guys” texts. They will be showing The World Cup and also have live music on Friday and Sunday! And book a Beach Shack for the ultimate experience here!
Roll with it!
The Friends of the Mary Ellen Welch Greenway hosts weekly Bocce games every Sunday at 4PM throughout the summer. You may also use the courts at your leisure and check out equipment, including bocce balls, rake, and broom at the YMCA during normal operating hours.
SPORTS!
Red Sox vs. Rays – Friday, July 17th at 7:10pm, Saturday, July 18th at 4:10pm and Sunday, July 19th at 1:35pm.
World Cup Finals – Argentina vs. Spain – Sunday at 3:00pm.
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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