Weekend Picks – May 15th

2.9 min readBy Published On: May 15th, 2026Categories: See & Do, See & Do0 Comments on Weekend Picks – May 15th

Happy weekend, Ctown!

$1 Duxbury Oysters at Tradesman

Join Tradesman Charlestown every Saturday & Sunday from 11AM–3PM for the freshest deal in town — $1 Duxbury Oysters! Pair your oysters with their signature Oyster Shooters or sip on one of the craft cocktails for the ultimate weekend vibe.

Whether you’re starting brunch, keeping it casual, or gathering with friends, this is the perfect way to spend your afternoon. No reservations required — just go hungry and get ready to Buck a Shuck!

It’s the perfect weekend for Cisco – whether you’re headed to the Seaport or Fenway!

Cisco Seaport season is back and better than ever! Enjoy this weekend’s sunshine and warm weather, with a cold Gripah, a cocktail by 888 Distillery, or some Nantucket Vineyards wine. You have to check out their Seaport venue updates, where you can now rent your own shACK and enjoy their new huge, tented stage area. You should also take a trip to their Fenway location, which has ballpark-inspired bites, is dog friendly like Seaport, and features live music on the week and on weekends.

Shop an epic thrift market at The Anchor on Sunday

The Style Exchange, a pop-up style Boston Community Thrift Market, is returning to The Anchor this Sunday, May 17th. What started as a single event has grown into a series of pop-ups across the city, creating a space where community members can sell their own clothing, shop more sustainably, and refresh their wardrobes without relying on fast fashion, making thrifting accessible, social, and intentional in Boston.

Story Time at the Garden starts on Saturday

Story Time at the Garden will start this Saturday, May 16! It will also take place June 20, July 18, August 15, and October 17th. Story time starts at Gardens for Charlestown at 9:30am!

Urban Wild’s Weekend Entertainment

Friday night — live band with @itsyaboykr bringing the energy all night long 🎸🎤
Saturday night — @djallstar401 takes over with the booth to keep you dancing all night 🎧🕺

Drinks flowing. Music up. Dance floor ready. Grab your crew and come dance with us this weekend.

Boston Launch Company’s May Hours

Boston Launch Company has created our favorite bar crawl – by way of water. Take the boat from Pier 6 in Charlestown, to Reelhouse Oyster Bar in Seaport, Tallship in Eastie, and Reelhouse in Eastie. They will operate from 11am to 11pm Friday through Sunday during the month of May. Call 617-504-6024 for a ride!

Check out Flight House Fitness at an Open House

Head to Flight House Fitness for an open house this weekend! You can visit Friday 2-6pm, Saturday 9am-2pm, or Sunday 10am-2pm. They are getting ready to open a massive new gym in Charlestown early June—and it’s aiming to be more than just another place to work out. Located at 465 Medford Street along the Mystic River, the 50,000-square-foot space is designed to bring everything fitness-related into one spot. Members will have access to a traditional open gym, group classes that blend strength and cardio, and even private recovery suites. The idea is simple: instead of juggling multiple memberships, you can do it all in one place. Read all about it, here!

SPORTS!

Red Sox vs. Braves – Friday, May 15th at 7:15pm, Saturday, May 16th at 7:15pm and Sunday, May 17th at 1:35pm.

NBA Playoffs – schedule here

NHL Playoffs – schedule here

Here are 9 places to watch the game in the neighborhood!

Check back as this list may be updated. Thank you to our Caught in Charlestown readers and Neighborhood Partners for supporting our local journalism efforts!

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