Forget the mall or shopping online! Shop local! Support our small businesses in the neighborhood!
Junebug
Junebug is a bright pink gift shop and floral studio located on Main Street. Whether you need a housewarming gift or a houseplant, Junebug is a one-stop shop. Junebug also has beautiful fresh-cut flowers to make the perfect bouquet for a friend or loved one or treat yourself!
Henry Bear
Henry Bear is an independent toy store that believes play is not only fun but also integral to physical, social, and mental growth. For over 45 years, they’ve been scouring the world to bring you high-quality, developmentally appropriate toys and games that inspire creativity, imagination, and exploration. This amazing toy store is located in Hood Park and has toys for babies to adults. Check out our feature on Henry Bear here!
Place & Gather
Sister store to Junebug, Place & Gather is the go-to home and lifestyle boutique for stylish and playful gifts! Showcasing quirky tea towels, stunning glassware, chic napkins, trendy candles, unique serving boards, and more, Place & Gather offers the cutest array of items that add a fun and thoughtful touch to any space. Perfect for impressing friends at your next get-together or finding the ideal host gift, their selection ensures you’ll find something special without taking things too seriously. This week, they just debuted a NEW line of children’s toys from Maileg Danish Design including a line of mice + mouse accessories, a castle, washing machine and tricycle! This line is a huge hit with the little ones. Plus, with tens of thousands of dollars donated to Charlestown organizations, you’re supporting a business that gives back to the community! P.S. There may be some construction on the street, but Place & Gather is open as usual, so come on by and check out their fabulous offerings!
Monroe Home & Style
This shop is an absolute dream. Monroe Home is a women-owned boutique in Charlestown that is all about thoughtful style. Their curated collection includes rustic artisan candles, vintage scatter rugs, and one-of-a-kind kitchen pieces that bring a unique charm to any space. If you’re looking for a little luxe gift, they have gorgeous gold rings, necklaces, indulgent self-care essentials, and cozy throws. They also carry elegant coffee table books and décor that strike the perfect balance of beauty and function. Whether you are shopping for a gift or just browsing, this boutique is a haven of inspiration—with personalized styling to match.
Kaybea Collection
This is another absolute favorite women-owned store in the neighborhood. It’s one of those stores where you just want to buy everything in sight. If you are searching for a stunning dress for an upcoming fall wedding or simply want to refresh your fit supply, it is simple: head to Kaybea. Their collection features the most adorable maxii dresses, along with a selection of gorgeous jewelry, chic handbags, cute tops, and trendy jeans and it is their high-end yet affordable fashion that really makes it easy to indulge. But that’s not all—Kaybea Collection is always getting involved in the community, regularly collaborating with other local businesses to bring unique and exciting offerings to Charlestown & beyond! Head to their site or follow them on insta to stay updated on their latest mashups and special events, as there is always something happening! And with their 2-year anniversary coming up, keep an eye out for a fabulous giveaway that you won’t want to miss, including 20% off Pistola for the upcoming homecoming event and a charm necklace giveaway on the Kaybea insta & TikTok!
Mockingbird Baby & Kids
Think shopping meets conscious living: this charming store is a treasure trove of adorable and high-quality essentials for all the little ones. From the cutest baby clothes, playful toys, and stylish kids’ apparel, Mockingbird has everything to make a child’s world a little more magical. Under the passionate ownership of Charlestown mom Lauren Thompson, Mockingbird offers a curated selection of eco-conscious, USA-made products and brands founded by women and minorities. Committed to sustainability, they use a “no frills” approach to packaging, relying solely on recyclable and reused materials to reduce waste. Proud supporters of local schools and nonprofits like Cradles to Crayons and the It Gets Better Project, Mockingbird ensures that every purchase contributes to a greater cause!
Slate
A year-round favorite for all shopaholics – use the excuse of celebrating fall 2024 with a wardrobe refresh at at Slate! Summer may be over but the Vineyard’s favorite fashion + lifestyle shop is not going anywhere. This Edgartown born shop and Charlestown neighborhood gem is brimming with an adorable selection of women’s clothing, from cozy sweaters to stylish denim that will keep you on-trend. Slate also has curated collection of accessories for the upcoming fall season, and they have a range of posh gifts that are ideal for treating yourself or a loved one.
Haute 44
Here we have yet another amazing, women-owned business (See a theme here? Go Charlestown!). Salon 44 and Haute 44 (the salon’s sister boutique) are both located at 44 Main Street in Charlestown. Haute 44 features everything from name-brand clothing to trendy jewelry, accessories, and gifts. Shop their beloved Charlestown collection and join the #44Gals community! Their Charlestown apparel is sold in all sizes, from kids to adults.
On Again Consignment
This luxury consignment shop is located on Main Street and is chock-full of amazing finds. You never know what you’ll find in the racks of this boutique that features women’s clothing and accessories.
Did we miss your favorite shop? Let us know in the comments below!

Massachusetts native and espresso martini devotee, Kayla Milofsky, is a 26-year-old physician assistant student at Mass General. The self-proclaimed Southie yuppie of three years graduated from Trinity College in 2021, majoring in neuroscience.
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