Walk with Me: 10,000+ Steps Exploring Boston
Written By: Sara Brown
As a remote intern with the Boston Preservation Alliance, I spend most of my days on a computer from the comfort of my home making content for social media or working on our website in Connecticut. But one day, I had the opportunity to be in Boston, visiting some of Boston’s Legacy Businesses. It was a matter of twelve hours, and over 10k steps later, I got to sample the best of what Boston has to offer!
WALK WITH ME!
This story began with the taste of a Strawberry acai refresher, and then I was ready to take the Green line, getting off at Hynes Convention Center.
Trident Booksellers and Cafe
I had to start a day of fulfilling adventures, and what’s better than a cozy cup of tea and a book? I highly recommend enjoying a cup of Blueflower Earl Grey while taking advantage of the outdoor seating. Trident Booksellers & Cafe has been on Newbury Street since 1984 and offers a wide range of tasty goodies, free wifi, and fun community events.
Newbury Comics
Anytime I’m in the Backbay I always make sure to visit Newbury comics. It’s a collector’s paradise, whether you’re into comic books, figurines, vinyl, or funky socks, their wide range of merchandise caters to all your nerdy needs. Locally founded in 1978 by two MIT students, this New England-wide business has been a well-loved retailer for four decades and spread to 26 stores across four states.
Winsor Dim Sum
After walking Newbury Street, the Public Garden, and the Common, I was ready for lunch in Chinatown. Luckily Winsor Dim Sum Cafe offers a variety of dishes that are friendly to a college student’s budget. 
The intimate dining space holds a few large tables and your dim sum items are ordered individually and served with jasmine tea. As someone who struggles to eat out due to dietary needs, this was perfect and the staff was friendly and happy to accommodate allergies. Various awards and achievements are framed on the walls boasting years of delicious service, it’s no wonder the City of Boston named Winsor Dim Sum a Boston Legacy 2023 Award Winner!
Brattle Book Shop
Founded in 1825, and under the Gloss Family since 1949, the Brattle Book Shop is a gold mine for used books. Three stories and outdoor shelves house well over 250,000 books, maps, prints, postcards, and more. I found it very easy to get lost in the pages of various books, spending a long time perusing the isles.
Capitol Coffee House
Walking along the Freedom Trail, I made my way to Capitol Coffee House. Unfortunately, I arrived just after closing but I did get to admire the facade. It is located in Sutton Corner, which is dedicated to William “Billy” Sutton who worked closely with John F. Kennedy. Most people say he was a loving person and he enriched the lives of all he worked with. For that reason, he was influential in Boston’s political landscape, thus why his legacy is cemented here.
CaFfe Dello Sport
A walk through Boston’s historic “Little Italy” will take you to a great place to watch live calcio (soccer) matches and sip espresso. This third-generation family-owned business offers various drinks alongside savory and sweet treats that maintain the Italian heritage of the North End. After a long day, I enjoyed a pistachio iced coffee, taking in the scenery from a comfy window seat.
Did I drink a concerning amount of caffeine, maybe? But I would say this was a successful trip exploring the Hidden Gems and Legacy Businesses of Boston.
Here’s my step count at the end of the day for proof. I have to admit I was thankful to see so many wonderful places, but I did spend the following day in bed resting!
Note: If you wish to recreate this trip, there are many ways to modify it so that it is accessible and user-friendly, such as using public transportation, taking more breaks, or splitting the journey over a few days!
Share your favorite Legacy businesses with the tags #PreservationHub and #SaveMyBoston. Not on Facebook, Instagram, or TikTok? No problem! Share your adventures and send us an email at admin@bostonpreservation.org.
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