What’s happening in Charlestown?
Yappy Hour
Wednesday, May 29th 5-8pm at The Anchor | Join Red Dog Resort & Spa, Charlestown Dogs, and The Anchor for Yappy Hour! There will be Pet Vendors, Pup Cups, Free Giveaways, and more.
Communi-Tea Dance
Thursday, May 30th 5-7pm at Dovetail | OutCharlestown is hosting a Communi-Tea Dance at Dovetail’s Patio to kick off Boston’s Pride Celebrations. Enjoy handcrafted drinks specials, complimentary bites, meet and mingle with fellow LGBTQ+ residents, and receive your free Bunker Hill Pride Hand Flag! Featuring special guest City Counsilor Gigi Coletta. Hop on the waitlist now!
Set Sail
Recognized as one of the top community sailing programs in the country, Courageous Sailing offers year-round sailing on Boston Harbor at Charlestown’s Pier 4! Whether it’s your first time on a boat or you have miles of water under your keel, there are various classes, memberships, and opportunities. Also known for its youth programming and its wildly popular summer day camp, they offer classes for kids ages 8 to 15. Read more about it here.
Free USS Constitution-themed Mini Golf
Bring your friends and family to try your hand at Constitution-themed mini-golf. Putt through History at a USS Constitution-themed 9-hole miniature golf course in the Navy Yard. The course is open during Museum hours, weather permitting. It is free for all ages, and no registration is required. Learn more!
MYSTRYDE’s Summer Sale
Now through midnight on June 7th, MYSTRYDE‘s Summer Unlimited Memberhsip is $675 and Summer Class 12-Pack is $285. Must be used in 3 months from date of activation!
Sports
Red Sox vs. Orioles, Tuesday May 28th at 6:35pm and Wednesday May 29th at 6:35pm. Red Sox vs. Tigers, Thursday May 30th 7:10pm and Friday May 31st at 7:10pm.
Get ready for the Boston Celtics to compete in the NBA finals!!! Check out our article about Canal Street’s Playoff Hub.
Head to Warren Tavern for the game and enjoy a cozy, energetic atmosphere. If you have a big party or want to play games while watching on a large drop-down screen, check out Urban Wild in Hood Park.
Coming up…
Saturday June 1st 8:30am-2pm | Blood drive by Bunker Hill Associates
Thursday, June 13th 6pm | Charlestown’s Got Talent at Eden Street Park
Saturday, June 15th 11am-3pm | Charlestown Block Party
Saturday, June 16th | Bunker Hill Day Parade & More

Abbey is the face behind Caught in Charlestown. In 2023 she migrated from Southie to Charlestown and brought the spirit of the ‘Caught In’ community with her. She is a new momma, creator, real estate agent, yogi, and so much more.
Liberty Tree Dedication in the Gardens for Charlestown
5 Things to Know This Week – May 19th
Weekend Picks – May 15th