Weekends Picks – May 29th

4.6 min readBy Published On: May 29th, 2026Categories: See & Do, See & Do0 Comments on Weekends Picks – May 29th

Happy Weekend, Ctown!!

Free Ferry Weekend Returns this Saturday and Sunday with Free Trips to Georges Island

Looking for a free way to get out on Boston Harbor? Free Ferry Weekend returns Saturday, May 30, and Sunday, May 31, offering free round-trip ferry service from Boston to Georges Island.  (Insider’s Tip: Be on the lookout for the Lady in Black.)

The annual event, presented by Boston Harbor Now in partnership with the Massachusetts Department of Conservation and Recreation, the National Park Service, and Boston Harbor City Cruises, gives families, residents, and visitors an easy way to experience one of Boston Harbor’s signature destinations without the cost of ferry tickets. Get more details here!

This Weekend: PickleBOS Charlestown Grand Opening

It’s finally here! PickleBOS, Boston’s premier indoor pickleball club, just opened their newest location in Charlestown. They are located at 440 Rutherford Ave., Ste 300… and there is free on-site parking!

This weekend they will host a grand opening event for everyone to check out the space and play! On Friday, May 29th, anyone can attend from 12-6pm, and there will be a Members Only event from 6-8pm. On Saturday, May 30th, anyone can check it out from 9am-5pm. Sign up now to reserve your spot!! Limit 1 event signup per person.

At the Grand Opening events, enjoy FREE:

  • Open Play
  • Intro Clinics
  • Food
  • And More!

Flight House’s Launch Party is this Saturday

Flight House, Charlestown’s massive new gym and wellness center, is hosting a Launch Party this Saturday, May 30th, from 8am to 12pm! It will feature their signature HYBRID workout followed by tours and socializing. During this time, everyone can enjoy a DJ on site, product sampling, and curated brand experiences from partners like Lululemon, Ruthie’s Juice (check out their pre-order menu!), Waverly, Athletic Brewing Co, Nutre, Apex Vitality, and more! RSVP here!

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 more about the facility and memberships, here!

Join an Intermediate Racing Clinic with Courageous Sailing

Courageous Sailing is hosting an Intermediate Racing Clinic on Saturday. This clinic will go through skills and drills to help intermediate sailors build their knowledge and become stronger racers. Each session will focus on a new topic, which will range from close-quarters boat handling, sail control, advanced wind awareness, etc.

These clinics will be run by Brad Churchill. Brad is the former coach of the BU Sailing Team and a very knowledgeable racer. He will incorporate his college coaching techniques into these sessions, giving you a taste of what it’s like to be on a sailing team. Given his background, the clinics will be largely focused on racing skills and strategies however these topics are useful and applicable for all different types of sailing. Regular attendance of these sessions will be helpful, as some of the content may build upon topics from previous weeks. 

Spring Into Summer Event at Philip Edward Salon on Sunday

Get ready to glow into summer with Philip Edward Salon! Join them on Sunday, May 31st for a day of sipping, shopping & self-care at their annual spa event, featuring their own offerings and community vendors. From 3-7pm you can enjoy:

  • Door prize raffle valued at $250
  • Mini spa offerings
  • FREE skin, massage, and wellness consultations/demos
  • Exclusive event packages + pricing
  • Retail discounts such as 20% OFF iS Clinical & Eufora retail
  • Pop-up vendors such as North End Acupuncture, Charlestown Candle Co., Salon 44 boutique items, and more
  • Food + drinks from Waverly Kitchen & Bar
  • Meet NP Alia for Botox, B12 Shots, and Filler consults!

$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!

Enjoy Cisco outdoors – 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.

Sun, cold drinks, and harbor views at Pier 6

Boston Eater came out with a list of the Best Views in Boston, and Pier 6 was included! This weekend, enjoy cold drinks and delicious food on the sunny patio or inside the restaurant, all with views of the water and city.

SPORTS!

Red Sox vs. Guardians – Friday, May 29th at 7:10pm, Saturday, May 30th at 4:10pm and Sunday, May 31st at 1:40pm.

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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