New annual tradition incoming … Charlestown Homecoming Weekend is back for another year, thanks to Visit Charlestown! It will take place September 20th and 21st, with a rain date of September 27th and 28th. They are excited to make it an even bigger community tradition this year.
“The goal of the weekend is simple: to welcome new residents to Charlestown and to celebrate the return of neighbors who’ve been away for the summer!”
Some of the schedule highlights include a morning workout at the Bunker Hill Monument led by MYSTRYDE, JPPilates & Monument Fitness, all-day shopping, dining, and exploring local businesses, pop-ups, and so much more.
If you are interested in participating as a vendor or volunteer, please email [email protected].
Junebug’s Outdoor Flower Arranging Class
On Saturday, September 20th from 3:00 – 4:30 pm, Junebug is hosting an outdoor flower arranging workshop in the Training Field!
With instruction from their talented team of designers, you’ll create a seasonal arrangement in a 6″ x 4″ vase using gorgeous autumnal blooms. Vase, scissors, floral mechanics, and all flowers and greens will be provided. As a bonus, all guests receive 10% off of Place & Gather merchandise after the workshop. A portion of the proceeds from this workshop will be donated to The Friends of the Training Field. Get your ticket now!
Ctown Homecoming Fitness Fest
Get ready, Charlestown! On Saturday, September 20th from 8:30 – 9:15 am, three of your favorite local fitness studios are teaming up for a fun, all-levels outdoor workout at the Bunker Hill Monument that you won’t want to miss. They’re bringing the community together to celebrate movement, connection, and the strength that makes Charlestown so special. Sign up now!! You’ll be led by an all-star trio:
🧘🏻♀️Jenn from @jppilates1
🏃🏻♀️Marguerite and Colleen from @mystryde
🏋🏻♀️Stacey from @monumentfitnesscharlestown
Together, they’ll guide you through a dynamic, stations-based workout featuring a mix of running, interval bodyweight strength training, and Pilates — all set against the iconic backdrop of the Bunker Hill Monument. Whether you’re a seasoned athlete or just getting started, this event is for everyone. Bring your friends, bring your energy, and let’s move together! Please wear sneakers and bring your own mat and water.
IONI is popping up at La Saison – and hosting a GIVEAWAY!
A giveaway featuring olive oil, sourdough, and coffee? Say no more. IONI Olive Co, a women-owned business that sells organic, Greek olive oil, is teaming up with La Saison for a giveaway that runs through their pop-up this Saturday, September 20th. Visit La Saison from 10 a.m. to 2 p.m. to learn more about IONI, and make sure you enter their giveaway before then! The winner will receive a 500ml bottle of IONI olive oil with a pour spout, a loaf of La Saison sourdough, and coffee for a week ($25 value).
Open House at Natural Glow
Stop by Natural Glow‘s Charlestown location on Saturday between 11am and 1pm for their open house! You can get a spray, enjoy mimosas, and shop package deals! Boston Belle will also have their new Charlestown sweatshirts for sale there… run, don’t walk!
Slate will host straND and Katherine Rose Collections
Handmade gemstone and glass bead jewelry shop straND will be popping up at Slate on Saturday, and Katherine Rose Collections, another beautiful jewelry designer, will be there Sunday!
Live embroidery at Kaybea
Kaybea will host live embroidery by Emilinas from 10am to 2pm on Saturday!
Tiny Ink Boston at Place & Gather
On Saturday from 10am to 2pm, Place & Gather will host Tiny Ink Boston!
Charlestown Nursery School’s Sunday Singalong
On Sunday at 4:15pm, join Charlestown Nursery School at City Square Park who will host Music at the Blissful for a sing along! All are welcome.
Essem Art Studio’s open house at the Kennedy Center
Say hello to Essem Art Stuio, have a donut, and meet the amazing staff at the Kennedy Center on Sunday from 10 to 11:30am! You can also enjoy a singalong and storytime with Miss Sophia at 10:30am! They’ll have limited number of take home craft projects available as well. Registration required to attend!
SALES SALES SALES!
Stop by LexRx and enjoy 25% off their skincare products!! Use code CTOWN25 to shop online. Our favorites are the Exfoliating Pads, Everyday Treatment, and the new Everyday Lip TX.
Check out Vivolo Wellness, Charlestown’s newest wellness studio! Take a walk into their lounge and enjoy $30 off all IVs, $10 off all injections, and 5-15% off B12 and NAD+ packages. On Sunday you can also book the Basic Bag for $20 off!
Philip Edward Salon is offering 20% off all hair services, 20% off all spa services, and 15% off retail purchases!
Check back for more updates, pop-up announcements, and 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.



5 Things You Should Know This Week – November 10th
Weekend Picks – November 8th
Coffee with a Cop in Charlestown on Wednesday November 19th – Stop by!