Boston’s 2.5 mile fashion freedom trail

If you’re visiting Boston (once all the snow disappears), walk the famous Freedom Trail (simply follow the red line) to thefrontsteps of Paul Revere’s home and the site of the Boston Massacre. 2.5 miles. Once you’ve taken in the city’s rich history, walk the 2.5 mile fashion freedom 11

“Fashion freedom trail? Never heard of it,” you mutter. That’s because I’m penning (well, typing) the idea after traveling to Boston over New Year’s. Thankfully, my trip was before the snow. The fashion freedom trail will take you through the Beacon Hills independently-owned boutiques on Charles Street. Next on your route are the Shops at Prudential Center (indoor mall). Finally, make your way up to Newbury Street and walk the double-lined shopping corridor on Newbury Street.

(through the park)

(along the river/through the park)


In the above maps, I planned my route (as a general guide) parking at 4 Newbury Street Garage. You’re encouraged to carve your own path, plus use Boston’s public transportation.

Newbury Street 

3365878744_3f2f19124d_o (2)
Photo Credit: MIT-Libraries

You’ll discover eight blocks of major retailers to independently-owned shops on Newbury Street (from Massachusetts Avenue to Arlington Street). Before you go, browse shops by category (ie. women’s fashion) on the Newbury Street site.

Lit on Newbury, Boston

My favorite store on this strip was Lit on Newbury (223 Newbury St.), a young women’s fashion boutique. I scored a Jealous Tomato top at 40% off but missed out on an Oliveacious camel colored faux leather halter (sold out of my size). If you know where I can get one, hit me up!

Make sure you stop by Fjällräven (304 Newbury). The Swedish-based outdoor apparel company has under 10 U.S. stores.

Other note-worthy stops along this shopping street include Second Time Around (324 Newbury Street), Hempest (207 Newbury) and Diane Von Furstenberg (73 Newbury Street).

Shops at Prudential Center (800 Boylston Street)


From high end staples such as Gucci and Swarovski to hip stores like Lululemon and Free People, THIS is mall shopping. The Shops at Prudential Center features over 75 stores. If you’re visiting between late March and November, book a famous water ride Duck Tour (departs outside Prudential Center). Check out information on parking rates for Prudential Center.

Boston duck tour

Charles Street

In the Beacon Hills neighborhood, stroll down Charles Street to shop independent boutiques like The Flat of the Hill (60 Charles Street), Uncle Pete’s (119 Charles Street) and KM Hudson (125 Charles Street). Better yet, check out this lovely piece on 16 Beacon Hill stores not to be missed from Boston Racked.

Uncle Pete's, Boston
Uncle Pete’s


KMHudson the bra store, Boston


The Flat of the Hill, Boston
The Flat of the Hill

Recommend your favorite stores and finds to the comments, or hashtag Native Gypsies (#nativgypsies) on Instagram to show off your fashions from Newbury, Charles or the Shops.





About Brooke ↞ Farm girl with a gypsy heart. Life-long obsession for junking and all things vintage. Working on on being a wife & mama, our next travel adventure, enjoying the little moments, colorful salads and a healthy earth. ↠ Read About BrookeRead more posts by Brooke

Leave a Reply

Your email address will not be published. Required fields are marked *