Beacon Hill's Best Shopping: Find It along Fashionable Charles Street

Beacon Hill is a classic Boston neighborhood with cobblestone streets and beautiful brownstones to be admired. Nestled within the snug quarters of Beacon Hill you'll find many small independent specialty stores that  sell everything a Beacon Hill resident may need, and lots that visitors will love. Stroll along Charles Street, where the majority of shopping and dining lives and you'll find an array of boutiques, and gift shops that will draw you in to browse and send you with bags filled with goodies to treasure.

Favorites among the fashionable women of the city include Holiday Boutique where you can shop from the racks or have a piece custom made. Ladies rave about Wish where you'll find an impressive selection of designer duds that aren't in every store. While Crush offers a full service experience offering shoppers personal shopping, and even private parties.

Those seeking New England themed gifts will easily be able to open their wallets at Blackstone's of Beacon Hill or The Flat of the Hill where you'll find an extensive selection of merchandise that will please everyone on your list.

With so much to offer in such a small section of this city, it is no wonder tourists and locals alike make Beacon Hill one shopping stop they never miss. 


Upscale second hand clothing is the focus of Second Time Around (sta). On Beacon Hill, Second time Around kicks it up a notch to ensure that its upscale clientele gets nothing but the best. Well stocked with gently used designer brands that aren't far off the runways, Second Time Around has a loyal following of locals who swear these clothes are better than is bought brand new off the racks of the fancy department stores. Stop in often as inventory is priced to move and flies off their shelves. Score designer duds at steep discounts and be the envy of your friends when you shop at Second Time Around.

Recommended for Beacon Hill's Best Shopping because: Beacon Hill's Second Time Around is a second hand store that carries quality consignments at great prices.

Jessica's expert tip: Second time Around takes time and effort, but the savings is worth every minute spent seeking the perfect item in your size.

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Black Ink began as a dream in 1994 of Susan & Timothy Corcoran. The small Beacon Hill storefront housed a massive collection of artistic rubber stamps and papers that quickly drew the attention of those seeking such items. Functioning as what they call a, "design laboratory" the owners learned what worked and didn't in their inventory and altered it to reflect customer's wants and needs. On their shelves you'll find a mix of industrial products like as store fixtures, functional home furnishings, like canvas hampers and other household items with purpose that are as attractive as they are necessary. You never know what you'll find when you walk into Black Ink as turn over happens often and the shelves are constantly restocked with new and exciting items.

Recommended for Beacon Hill's Best Shopping because: Shopping at black Ink is a treasure hunt; here you'll come across an eclectic mix of items you'll just have to buy.

Jessica's expert tip: Go to Black Ink without a purpose; shopping here is more fun when you stumble upon something special rather than fulfill a need.

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Wish boutique has been offering the women of a Boston a unique, fashionable shopping spot on Beacon Hill's popular Charles Street for years. Wish fills its racks with the popular designers you know and love, like Trina Turk, Theory, Joie, and Nicole Miller, Velvet, AG and Hudson. Stocking its shelves with only the best of the best that these designers have to offer each and every season. Small in scale, it is frequent quick stop for local ladies looking for something special that won't be seen on everyone else. Neat and orderly, you can easily peruse the shelves lined with gorgeous finds.

Recommended for Beacon Hill's Best Shopping because: Beacon Hill's Wish boutique is filled with designer duds you won't find on everyone; ideal to grab something special that will turn heads.

Jessica's expert tip: Wish is a small boutique worth a look fro something special. You will spend a little more, but you'll be assisted by very helpful sales associates, and your outfit will be unique.

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Paper may seem passe but at Beacon Hill's Rugg Road paper is serious business. Selling everything from wrapping paper to invitations Rugg Road elevates paper to a higher standard that is cherished by those who find value in beauty. An excursion to Rugg Road brings back memories of snail mail, and the joy of finding with the box outside a handwritten note on beautiful stationary. Custom invitations are waiting to be created while sketchbooks and journals fly off their shelves. Hung with care are racks of wrapping paper and ribbons to wrap perfect packages to be given to someone special. Indulge in a few sheets of handmade paper and choose the words you place on these fine sheets with care.

Recommended for Beacon Hill's Best Shopping because: Beacon Hill's Rugg Road sells quality paper goods ideal for gift giving be it the wrapping or what's inside.

Jessica's expert tip: Rugg Road is a full of gorgeous paper products; peruse carefully as you could overlook the most beautiful item.

Read more about Rugg Road Paper Company →

When childhood friends Rebecca Penner and Laura Macris decided to put their years of playing with and learning about fashion into four walls of a boutique, they opened Crush. Focusing on giving customers a hand picked selection of best women's contemporary fashion they could find, Crush focuses on juxtaposing up-and-coming designers like Rory Beca and Yumi Kim with celebrity loved lines like Alice + Olivia, J Brand and House of Harlow. Crush provides the fashion forward woman a shopping experience like no other. With two Boston shops and an online experience for those who can't make it in, you'll never be without their savvy style. Crush offers services most spots do not like personal shopping, private shopping parties and closet cleanses; they'll ensure you are always stylish.

Recommended for Beacon Hill's Best Shopping because: Crush is a Beacon Hill boutique that offers services beyond the "norm" like personal shopping, private parties and closet cleanses.

Jessica's expert tip: Take advantage of the staff's style knowledge to find a fit you're happy with in a style you love.

Read more about Crush Boutique →

Red Wagon
Photo courtesy of Jessica Polizzotti

Red Wagon offers parents looking for cool styles that won't be on every kid you know the chance to shop in a small setting. Here you can create a wardrobe of items that speak to you, but come with high price tags. A few novelty and toy items allow you to indulge your inner child while selecting garments for everyday. A favorite among city residents searching for that special something for a youngster that just can't be bought in a big-box store, and visitors looking for something special in Boston, Red Wagon has it all. Grandparents go gaga over the toys that bring back memories of their youth and buy to share with the little ones they love. The selection of specialty items, apparel, toys and books changes regularly and allow for seasonal updates.

Recommended for Beacon Hill's Best Shopping because: Adorable kids fashions and a few novelty items make Red wagon a local favorite on Beacon Hill.

Jessica's expert tip: This is a favorite for those seeking a gift that they know no one else will give (grandparents go ga-ga over the toys that are a blast from their past).

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As a neighborhood boutique, making its home in the posh and fashionable neighborhood of Beacon Hill, Moxie specializes in contemporary designer shoes, bags, accessories and apparel for women who want to remain fashionable. Whether at work or at play Moxie brings big style to your daily life. At Moxie, big city fashion and small town charm come together on their shelves. You'll find a top notch selection of designer duds that are hand-picked by the Moxie staff. All the goods are high end, the atmosphere is welcoming and relaxed making you feel at home while you shop for that perfect something.

Recommended for Beacon Hill's Best Shopping because: Beacon Hill's Moxie has one of the best selections of designer shoes in the city.

Jessica's expert tip: Walk into Moxie ready to spend, but play with everything inside until you find that special something you must buy.

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The Flat of the Hill is a charming gift shop where you'll encounter lots of unique items to take back home. Along with the extensive selection of gift items that will catch your eye (black and white photos of New England, garden accessories, soaps, candles, painted furniture, napkins, picnic baskets, decorative pillows, handbags, silver trays, and hand-painted signs) you'll find a fashionable array of jewelry and handbags. Locals frequent this gift shop to send purchases to family and friends who are out of town, and bring a little Boston into their lives. Add a friendly staff and a relaxed atmosphere and Flat of the Hill offers a wonderful shopping experience.

Recommended for Beacon Hill's Best Shopping because: The Flat of the Hill is a gift shop that carries a wonderful selection of Boston themed items that are anything but tacky.

Jessica's expert tip: Check out their Facebook page and sign up for emails to score some great deals.

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Jessika Goranson opened Holiday Boutique in and has grown this favorite Boston boutique quite a bit since that time. Holiday exudes femininity from the decor to the attire within; this is the place to shop for all those girly girls out there. The store is stocked with clothing from designers from smaller fashion houses both in and outside the U.S. Add to the designer goods a hand made selection of celebratory dresses, skirts and tops, and you are sure to find something to suit you. THe fun does not stop there because Holiday takes their goods to another level by offering a re-worked vintage label, "Holiday-Pretty Little Vintage". And even a signature cashmere collection.

Recommended for Beacon Hill's Best Shopping because: Whimsical and old fashioned Holiday is a modern day boutique that is not to be missed.

Jessica's expert tip: Order a custom made creation and enjoy this special little item for years to come.

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Blackstone's is the gift shop that you can't miss. Selling a little something for everyone, the unique finds in this Beacon Hill shop will fill your needs. Everything from seasonal gear like Derby hats, to specialized items to inspire can be found under this shop's roof. Blackstone's of Beacon Hill carries an Boston mementos that are ideal to bring back as a way to remember your favorite aspects of Boston. These items include Make Way for Duckling themed products, sports team paraphernalia and books by local authors. While strolling Charles Street be sure to make time for shopping, and get your gifts at Blackstone's of Beacon Hill.

Recommended for Beacon Hill's Best Shopping because: Blackstone's is a Beacon Hill gift shop filled with items that have personality and will be cherished long after purchased.

Jessica's expert tip: Themed and seasonal items make Blackstone's one place you must stop over and over again.

Read more about Blackstone's of Beacon Hill →


Meet Jessica Polizzotti

Born and raised in Boston, Jessica knows her city like the back of her hand.  Always looking to uncover something new, Jessica keeps up on the latest and greatest Boston offerings. 

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