Forget the mall, or schlepping into Newbury Street, we’ve got our own wonderful small businesses right in Charlestown for all your personal shopping and gift-giving needs!

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’s Park

Henry Bear’s Park 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. Plus, with tens of thousands of dollars donated to Charlestown organizations, you’re supporting a business that gives back to the community!

Monroe Home

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.

They also have officially been named a winner in the Best of Boston Home 2025+2026 awards by Boston Magazine. The boutique took home top honors in the Home Accents, Boston category.

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 winter 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!

Joy Street Kids

 Joy Street Kids, the local brand known for their playful, city-themed pajamas and super-soft kiddo staples, has officially taken over the Mockingbird Baby Kids Clothing space on Main Street – complete with a name change! If you’re not familiar with Joy Street yet, get ready to fall in love. Their Boston-inspired prints, bright colors, and comfy fits have been a hit with families across the city. And now you can shop it all right here in Charlestown!

Main Street Pasta + Wine

Two of our favorite things! Pasta and Wine can be the perfect gift! Main Street Pasta and Wine has thoughtfully curated gourmet foods and wines. They can also help you build a custom gift bag and have gift cards, too! Learn more here! 

Did we miss your favorite small business? Let us know in the comments below!