Weekend Picks – August 14th
Happy weekend, Ctown!
The Kennedy Center will host SkateFit on Friday
Roll into the weekend with SkateFit Charlestown! This Friday, August 14th from 5:00–7:00 PM, The Kennedy Center is transforming Harvard Kent Playground into an outdoor roller-skating party! Pre-Registration is required before the event, so be sure to sign up in advance. Don’t miss this chance to skate, dance, and make summer memories with your neighbors!
✨ All ages are welcome.
🎵 Music, skating, and community fun.
🛼 Bring your own skates or borrow a pair on-site.
Check out Ruthie’s Juice Mini Main Street!
The cutest new kid’s play space has arrived in Charlestown, and it’s right inside the kid’s cafe at Ruthie’s Juice! Stroll down to relax with your favorite juice, smoothie, or bowl while the kids play in the pace designed to look like a mini Main Street, featuring a Monument and Junebug storefront, plus a theater stage!
Boston Lyric Opera: Street Stage is coming to the Charlestown Navy Yard on Saturday
This Saturday, August 15th at 3:30pm, join Boston Lyric Opera at the historic Charlestown Navy Yard for a memorable afternoon of music, maritime history, and stunning Boston Harbor views. From the lawn of the 1805 Commandant’s house, BLO’s musicians will perform an open-air concert of fan-favorite opera and musical theater repertoire, all in sight of U.S.S. Constitution and U.S.S.Cassin Young. Experience songs from across centuries as we celebrate the founding of the Charlestown Navy Yard, with special events happening throughout the weekend.
This program is free and recommended for audiences of all ages. Playbills with texts and English translations of the multilingual program will be provided on site. This is a free event! (Rain Date: August 16, 3:30 pm – 4:30 pm)
It’s still summer at Kaybea… and don’t miss their Shorts Sale!
We still have a solid month and a half left of shorts season, so here’s your sign to shop at Kaybea because their shorts have officially gone on sale! Check out this fun post pairing each pair with a curated outfit.
Plus, there are plenty of summery dresses, fun pants, and cute bags to shop for your remaining summer events – and there are even some beloved East Coast and Sardine crewneck sweaters still in stock!
Last call for Dine Out Boston
Dine Out Boston® is back for its summer edition from August 1-15, 2026. Presented by Meet Boston, and in partnership with the Massachusetts Office of Travel & Tourism and new sponsor Toast, this two-week culinary celebration features close to 200 participating restaurants, providing diners an opportunity to enjoy delicious deals and restaurateurs the chance to bring in new patrons to their establishments.
For the first time, this year’s summer program spans three Saturdays. Participating restaurants will offer prix fixe menus for lunch and dinner, with many offering takeout and delivery options as well. Restaurants select one of three price points and customize their lunch and dinner menus: lunch at $27, $32 or $36 and dinner at $38, $46, or $55. Restaurants can offer as many courses as they desire at their selected price. A full list of participating restaurants is here. Their website seems to be glitching, but here’s where you can go in Charlestown:
- Waverly: Lunch is $27 pp, Dinner is $46 pp. Check out the menus!
- Monument: Lunch is $27 pp, Dinner is $38 pp. Check out the menus!
Sweat & Social Sundays by Volo
Head over to Club Volo Assembly Row every Sunday for their bi-weekly 45-minute Pilates series at 9am. Kick off your morning with an energizing, all-levels flow intended to help you reset and feel your best heading into the week Whether you are a regular on the mat or trying it for the first time, this welcoming class blends movement, breath, and good energy in a laid-back environment. Stick around after class to hang out, meet new people, and enjoy the Club Volo space before heading out to enjoy your Sunday. Sign up here!
Don’t miss Tradesman’s EVERYTHING $10 Menu this month
Run, don’t want to Tradesman in Hood Park… EVERYTHING on the menu is just $10 in August. Food. Drinks. Pizza. Cocktails. All month long. This special is dine-in only, so make your reservations now!!
It’s our way of saying thank you to the Charlestown community for all of your support—but everyone is welcome to join us!
Check out Flight House Fitness at one of their ongoing weekend programs
FREE CLASS FRIDAY (Fridays, all day)
Every Friday this summer, all HYBRID, LIFT, and SCULPT classes are free for everyone.
- HYBRID: Functional strength and conditioning designed to build athletic, everyday fitness.
- LIFT: Progressive strength training focused on building muscle and improving performance.
- SCULPT: A low-impact, full-body studio workout focused on strength & endurance.
RUN CLUB (Saturdays, 8am)
Join the Flight House Run Club every Saturday for a free, community run starting and ending at Flight House. The route is approximately 3.5 miles, all paces are welcome, and it’s open to both members and non-members. Keep an eye out for special Run Club collaborations throughout the year!
SUNDAY RECOVERY (Sundays, 8am to 2pm)
Start your week feeling your best with Sunday Recovery, hosted by Apex Vitality, the official health partner of Flight House Fitness. Enjoy rotating recovery services each week at exclusive pricing. Their expert care is designed to help you recover, recharge, and perform at your best.
Rent a shACK at Cisco
Cisco is the perfect weekend hang out 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 have live music on Friday, Saturday, and Sunday! And book a Beach Shack for the ultimate experience here!
Ritual x Handle Bar Wellness Social Event at Park City
Wellness in Southie is getting an upgrade! Ritual and Handle Bar have curated the perfect start to your Saturday! Join them on August 15th for a multitude of events including, The RITUAL Run Club starts at 9am and a choice of 2 classes, a HIIT bootcamp (9AM) and Handle Bar Pilates (10 & 11AM). The after party will feature cold plunges, live music, and multiple pop ups of wellness vendors. Stick around and enjoy the day at Park City, live music starts at 1pm. Get your tickets here!
SPORTS!
Red Sox vs. Pirates – Friday, August 14th at 6:40pm, Saturday, August 15th at 7:15pm and Sunday, August 16th at 1:35pm.
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!
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.
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