The next time I return to Boston, I’ll do so again in the fall, and this time, I won’t leave until I’ve seen the entirety of New England!
Boston, Massachusetts is glorious in autumn. Deep shades of orange, cheerful yellow, and inspiring red. The delightful Charles River, the nostalgic back to school feeling, and above all else, Halloween.
A friend and I spent 72 hours in Boston, Cambridge, and Salem Massachusetts in October 2018. The motive? Enjoying my favourite holiday and taking in the filming location of Hocus Pocus, the classic nineties Halloween film starring Bette Middler and Sarah Jessica Parker.
After only three days, I added a road trip through New England (all six states!) to my travel bucket list. If you’re like me and only have 72 hours in Massachusetts, here’s how to spend it.
Explore the Boston Public Market
We stayed nearby at an Airbnb in Revere. The blueline subway was a quick 15 minute ride from Beachmont to Bowdoin station (downtown Boston).
Exit the train and meander past City Hall until you find yourself at the Boston Public Market. You’ll find local goods from artisans, bakers and baristas. We started each morning at the market with a helping of oatmeal and a fresh smoothie.
Take the Old Town Hop-On Hop-Off Trolley Tour
We got unlucky with the weather (unprecedented wind and rain storms) so opted for a tour on the Old Town Hop-On Hop-Off Trolley. The day pass allows you to cruise the entire line, or pop on and off at points of interest.
TLW tip: Luxury Wanderers belong in the Back Bay area. Locals shared that monthly rent is in excess of $10,000 USD. No surprise why it was once home to athlete Tom Brady.
Take in a Sports Game
Boston is home to a number of sports teams with storied histories. Take advantage and buy tickets for a game (or two!). Our evening ended with a night at TD Garden watching the Montreal Canadiens defeat the Boston Bruins, 3-0.
Boston Public Library
For a reprieve from the rainy walk, we popped into the science Boston Public Library, sauntering through rows of books and paging through a few written about the city of Boston. Nearby is Copley Square—the iconic marker of the Boston Marathon.
Walk the Freedom Trail
Wander the Freedom Trail in downtown Boston, visiting Faneuil Hall Marketplace, also called Quincy Market and learn more about Boston’s rich history. Grab a bite from a local vendor, and pick up your “wicked smaht” souvenirs.
Save room for dessert from Magnolia Bakery—you won’t be disappointed. Having been to New York City and missing Magnolia Bakery, founded in NYC and made famous by the Sex and the City series, I was pleased to try a lime cheesecake.
Walk that off and when you’re ready for another bite, hit up Boston’s Little Italy. Enjoy the people watching and stop for cannoli at Mike’s Pastry. Rumor has it many Bruins’ players call Little Italy home.
From there, cross Harvard Bridge (or grab the subway that spans Longfellow Bridge) to Cambridge. Both traverse the Charles River, an area that’s chock-full of runners training for the Boston Marathon.
Cambridge: Massachusetts Institute of Technology and Harvard University
On your way to Harvard you’ll pass Massachusetts Institute of Technology, a prestigious, top-ranked academic institution in the world with an acceptance rate of just seven percent!
You’ll soon find yourself at Harvard Square, bustling with students and tourists alike. Harvard sprawls over 5,000 hectares so enjoy the afternoon, grabbing a bite before heading back over the river.
The Boston Red Sox won the World Series during our stay in Boston, making our visit to Fenway that much more eventful. The site was packed with adoring fans and giddy journalists. We made the loop around, shot a few photos and carried on.
That afternoon we took the city bus for a 70 minute ride from Boston to Salem. I can’t recommend this enough. I thoroughly enjoyed the tour through small town USA, eventually landing at our destination: Salem, the (arguable) Halloween Capital of the World.
Take a Walking Ghost Tour
After touring the town on our own visiting the Witch House, Old Burying Point Cemetery and Bewitched Statue of Elizabeth Montgomery, we took a guided walking tour through the town. The historic tales were eerie, and well worth the pre-booked, $12 tickets.
Spending an evening in Salem the weekend before Halloween was a blast, and very busy. The best part? The Hocus Pocus, Sanderson sister impersonators! There were at least three different trios, all happy to stop and take (unpaid) photos.
After dinner at Turner’s Seafood, one of America’s top ten most haunted restaurants, we bussed back to Boston.
Live Like a Local
We finished our final evening in Boston at a pub, a burger in hand, watching the Patriots game. When in Boston!
Back to Boston? Absolutely!
To me, luxury travel means spending less on air travel and accommodations and more on experiences and food. We found as efficient a route as possible, a highly rated Airbnb outside of Boston proper, and took advantage of the subway and our healthy legs.
When I undoubtedly return to Boston, I’ll do so again in the fall, and this time, I won’t leave until I’ve seen the entirety of New England.
Deana is a writer, content marketer, operations manager, and big dreamer. For her, travel amounts to architecture gazing, market shopping and people watching at sidewalk cafés. Most importantly, when traveling she wanders endlessly on foot.