Boston, Massachusetts
“When I think fall, I think Boston,” Matt told me when I asked him where he wanted to go during Halloween weekend.
“Tell me why you think that,” I insisted. “You’ve never been, right?”
“I don’t know,” he replied with a shrug, “I just think Boston screams fall.”
And with little more to go on, Matt and I booked our Halloween trip to Boston. The city, with its colonial charm, historic neighborhoods, cozy cafes, and blustery autumn weather, did not disappoint.
On our first day in Boston, Matt and I, along with our best friends Kelsey (of Kelsey Prater Photography) and Saxon, began our excursion on Newbury Street downtown, where we strolled down a store-lined avenue gazing at posh window displays and occasionally popping into shops to buy gloves, winter boots, a scarf, or another pair of gloves (yes, we Tennesseans were vastly underprepared for the 30 degree weather).
Fully bundled, we then made our way to the gilded halls of the Boston Public Library.
There, we posed for photos on the top of its sweeping marble staircase, pointed out our star signs painted in the stonework beneath our feet, traipsed around the outdoor fountain, and spoke in hushed whispers rooms filled with people reading by the light of green-glass lamps, sunlight streaming in from the windows to illuminate the ancient-book-dust swirling around our heads.
When we stepped out onto the street again, blinking at the hazy autumn sun, our path took us across Copley Square with its Tortoise and Hare statue (where Matt scared a flock of pigeons) and Trinity Church, a 19th-century Episcopalian parish.
Before making our way too far into the city, I insisted that we take the advice of a coworker and visit “the most photographed street in America”: Acorn Street. And I can totally see why this place fits that descriptor—chunky cobblestones, patriotic American flags, charming red brick apartments. It’s everything you could want in a photo, and yes, we did take a million pictures here.
The highlight of our meanderings was the Boston Commons, Boston’s spacious downtown public park. As I stepped onto the familiar green space, filled with kids and dogs and squirrels, I couldn’t help but think of some of my favorite authors whose books seemed to be filled with references to this beloved urban playground (especially Jhumpa Lahiri, who lived in Boston and whose works burst with mentions of the city).
We stopped at the famous “Make Way for Ducklings” installation and wandered in and out of the trees, marveling at the reds, oranges, and yellows of the changing leaves. And when a few squirrels ran up to us, curiosity and hunger writ large on their faces, we did the natural thing and fed them by hand.
Feeding squirrels in the Boston Commons is totally a thing in this city. Saxon, who lived in Boston for two years, showed us his method: he enticed the squirrels with crushed peanuts that he’d nicked at Panera earlier that morning. As the furry little creatures approach, you can either let them eat the peanut right out of your hand—some will take it from you with their tiny paws, whereas others will just eat right out of your palm—or you can do the crazy thing and let them climb up your pants. Matt chose the riskier route.
After taking a few passes of the hand sanitizer, we exited Boston Commons as new wildlife warriors, ready for another adventure: the Freedom Trail! You thought I’d never get to it! The Freedom Trail is a two-and-a-half mile-long pathway that runs through downtown Boston, passing through 16 locations significant to the history of the United States. The pathway is marked by a beautiful red brick that leads explorers from landmark to landmark, starting at the Boston Commons and ending at the Bunker Hill Monument in Charlestown.
We didn’t unwaveringly follow the Freedom Trail at any point during our time in Boston, but we did let it lead us to certain landmarks of interest, the first of which was Granary Burying Grounds. This is Boston’s third-oldest cemetery, founded in 1660, and is remarkable because it is the final resting place for many Revolutionary War-era patriots (i.e., Paul Revere, the victims of the Boston Massacre, Samuel Adams, John Hancock, and Robert Treat Paine). The cemetery has just over 2,300 grave markers, but historians estimate that as many as 5,000 people are buried in it.
Matt was especially intrigued by the age of the graves—many were from the late 1600s, and some of our favorites bore the piratical “Skull and Crossbones.”
After haunting the graveyard for a bit, we wandered past the original state capitol building and site of the Boston Massacre, where British soldiers shot and killed five people in 1770. We then left the Freedom Trail behind for some Poshmark shopping (where we stocked up on sweaters, leggings, and jackets). It was at the end of our shopping extravaganza that we realized we were starving. And it was cold!
With hunger on our minds, the four of us drifted towards the waterfront and into Faneuil Hall Marketplace, which houses the famous Quincy Market, a huge shopping center along a long cobblestone promenade packed with restaurants.
Matt and Saxon went straight to Boston Chowda for lobster rolls while Kelsey and I grabbed naan and biyrani from Gourmet India.
The four of us found a place to eat in the crowded, airy rotunda and ate in near-silence, enjoying people watching and resting our tired feet. I even changed shoes! With full stomachs, we hopped across the street to the marketplace’s namesake, Faneuil Hall, which was a public meeting area for colonists in the late 1700s.
During our tour of the building, we learned that this space was where colonists first protested the Sugar Act in 1764, established the doctrine of “no taxation without representation,” where Samuel Adams rallied the citizens of Boston to the cause of independence from Great Britain, and where George Washington toasted the nation on its first birthday. Through the years, it has continued to play host to countless famous orators, including Supreme Court justice Oliver Wendell Holmes, Susan B. Anthony, and Ted Kennedy, thus living up to its nickname as the “Cradle of Liberty.”
Later in our trip, we would stop for breakfast at one of the oldest pubs in Boston, The Green Dragon Tavern, which is located in this same central square. Established in 1714, this pub saw the likes of Paul Revere, Sam Adams, John Adams, John Hancock, and Daniel Webster plan the Boston Tea Party as well as the defense of Lexington and Concord (which later spurred Paul Revere’s famous ride). (Pictured below is another old pub, The Bell in Hand).
But we still had exploring to do, and next up was my very favorite place to visit in Boston—Abigail’s Tea Room.
The tearoom is everything you could want out of a trip to Boston: bottomless cups of the five teas that were tossed overboard during the Boston Tea Party in 1773, a view of the downtown area and its tall, bright buildings whose windows reflect the endless blue of the harbor waters, and a replica ship and museum where you can watch colonial-clad men and women reenact the Boston Tea Party by throwing crates of “tea” into the harbor, complete with historic garb, accents, and lingo.
It’s great fun. Matt and I purchased a Boston crème pie, a cranberry orange scone, and two bottomless teacups. Between the two of us, we tried all five of the teas laid out for us as we watched “colonists” shouting about the British and chucking things off the ship.
Most of the teas were fairly classic: green tea, black tea; but if you’re feeling adventurous, give the “Souchong” a try. I’ll liken my experience of this tea to inhaling tons and tons of bonfire smoke. Even as I write this two months later, I can smell it—that stuff will knock you back.
After making some choice purchases at the museum gift shop (who can resist a miniature glass teapot??), the four of us strolled along the harbor, stopping to watch the playful seals swim outside the Boston Aquarium.
Just as the sun started to set on our magical day in Boston, we followed the Freedom Trail to the place where freedom began—the Old North Church made famous by Paul Revere’s midnight ride. Do you remember the expression, “One if by land, two if by sea”? It was at this church on the night of April 18, 1775 that Paul Revere lit two lanterns to warn the colonists that the British were taking boats across the Charles River! It is said that the lanterns hung for just under a minute to avoid detection by the British troops occupying the city.
For the history buffs out there, you can read more about what happened after that in my post about Concord. Later in our trip, we revisited the neighborhood where the Old North Church sits, Little Italy, in order to have a go at some of its famous bakeries. Before heading to the airport, Matt and I literally stuffed our carry-on bags full of chocolate éclairs, cookies, chocolate-dipped pretzels, nutella cheesecake, and cake balls.
Needless to say, Boston is a history buff’s paradise, but it’s also the prettiest urban city I’ve ever visited. The modern and the new tastefully preserve the historic and the patriotic; the two worlds complement each other rather than overwhelm or discard. And if you ever visit Abigail’s Tea Room, please try the Souchong and tell me what you think of it!
