On the Freedom Trail: Boston and Concord, MA

In April, we headed north to Boston for our friends Joe and Lily’s baby shower. The last time we were up that way, we were celebrating their wedding in Providence, Rhode Island (see our blog on that trip). This visit felt like a full-circle moment—reconnecting with them and their families as they prepare to welcome their newest addition. Just like during the wedding weekend, we carved out time to explore. This time, we had the best kind of guides: our soon to be parents, eager to show off the highlights of their home turf.

Friday: Echoes of Revolution in Boston

We left Raleigh in the morning and landed in Boston around midday. Public transportation is one of our favorite ways to get a feel for a new place (especially since Raleigh’s options are… limited), so we hopped on the subway from Logan International into the heart of the city.  Our first stop was The Well Coffee House – a cozy spot where we grabbed coffee, stashed our luggage using Bounce, and fueled up for an afternoon of exploring.

We kicked things off with a VoiceMap audio tour through the North End—Boston’s oldest neighborhood, where colonial echoes mingle with the scents of Little Italy. Our tour began at Copp’s Hill Burying Ground, the city’s second-oldest cemetery. From this peaceful perch, we caught stunning views of the harbor, marveled at one of the city’s tiniest homes across the way, and learned about the notable figures buried there—including Rev. Cotton Mather, whose sermons helped spark the Salem witch trials.

We continued along the Freedom Trail toward the Old North Church, where Robert Newman hung the two lanterns (“one if by land, two if by sea”) to signal Paul Revere. The trail then led us to the Paul Revere Mall, a charming greenspace named for the midnight rider himself. Blooming trees and dogs at play made it easy to forget we were in the middle of a bustling city.  

As we wandered through Little Italy, the irresistible smells were interrupted only by our guide’s account of the 1919 Molasses Flood, which left the neighborhood literally sticky for days. Further along, we passed the Old State House, a red-brick witness to some of the earliest protests against British rule. Every cobblestone seemed steeped in revolutionary spirit.

Boston’s history is also deeply intertwined with its immigrant roots. One of our final stops was a monument honoring Irish immigrants who fled the 1847 famine. Many chose Boston as their new home, and today the city hosts one of the largest St. Patrick’s Day celebrations in the U.S.

We wrapped up the tour at Boston Common – America’s oldest public park, dating back to 1634 – and the adjacent Public Garden. This may have been our favorite stop. With trees just beginning to bloom and the city buzzing quietly around us, we lounged on a bench soaking up the sun. Nearby, the iconic swan boats made their slow, graceful laps around the pond, a charming tradition since 1877. Just across the water, a small crowd gathered to take photos at the now-famous Good Will Hunting bench—where Robin Williams and Matt Damon filmed one of the film’s most memorable scenes. 

For dinner, we met up with Joe and Lily at Buttermilk and Bourbon in the Back Bay area. The southern biscuits were worth writing home about, and we sampled New Orleans-inspired small plates and craft cocktails that hit the spot. After dinner, we hopped on the train with them and made our way to Concord for the weekend ahead.

Saturday: Baby Shower & Family Time

Saturday brought us to a beautiful baby shower at the local country club, where we celebrated Joe and Lily with a buffet-style brunch, pastel baby blocks, and adorable cupcakes and cookies from a local bakery. We wrote notes of encouragement for Lily to read during labor (though our confidence quickly wavered during the baby trivia—we’re clearly not experts on diaper stats). The day ended with gift-opening and happy tears as tiny onesies and baby books made their way into Joe and Lily’s hearts.

That evening, we returned to the cozy Airbnb hosted by Lily’s aunt and uncle, where we were warmly welcomed into family dinner. We wrapped up the night with pizza, shared stories, and a quiet game of chess. It felt like the kind of night that didn’t need to be photographed or posted—just lived and cherished.

Sunday: Revolutionary Roots in Concord

After Lily’s extended family departed on Sunday morning, Joe and Lily took us on a sightseeing tour around Concord. Our first stop was the Old North Bridge or better known as the site of “the shot heard ’round the world”. It was here on April 19, 1775 that the British fired on the Concord Minutemen, sparking the Revolutionary War. Standing there, in the shadow of the Battle Monument erected to commemorate the lives lost on that spring morning 250 years ago, we certainly felt the gravity of that fateful, bloody day. After soaking the moment in, we moved up the hill just a stone’s throw away from the bridge, where we toured the Old Manse House, a historic home once occupied by literary legends like Ralph Waldo Emerson (who wrote Nature there) and Nathaniel Hawthorne. Inside, the rooms practically hum with creative energy.

We then made our way to downtown Concord and The Cheese Shop to pick up lunch for a lakeside picnic. The artisan sandwiches made our picnic by Walden Pond, made famous by Henry David Thoreau, one to remember. After trying to stroll some of the shorelines that inspired Thoreau’s simple-living experiment, we were forced inside to the visitor’s center to escape the wind. There, we nerded out over the interactive “Where Is Walden?” exhibit—pinning our favorite nature sites on a touchscreen map, learning about Thoreau’s explorations, and checking out a replica of his cabin.

Our final stop was the Concord Museum, where spinning wheels and colonial tools whispered stories of everyday patriots. We came full circle as we stood before the very desk where Thoreau wrote Walden, a tangible reminder of how history and nature intertwine here.

That evening, we shared one last meal with Joe, Lily, and her aunt and uncle. Joe cooked up an incredible shrimp pasta with homemade pesto, and we capped off the weekend with wine, stories, and deep gratitude for such a meaningful visit.

The next morning, Daniel and I caught an early Uber back to Boston for our flight, already reminiscing about our weekend filled with friends, food, and footsteps through history. We’d highly recommend taking a trip to Boston and Concord, even if you aren’t a history buff; there is nothing quite like standing where this great experiment we call America began.

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