By Nolan Leonard ’26
When people are making plans for spring break, they may think about escaping cooler weather to soak up the hot Florida sun. However, I enjoy all different climates and was thrilled to spend my time off in Boston, MA. For as long as I can remember, “Beantown” has been at the top of my bucket list. I adventured to explore a beautiful city filled with rich history and a plethora of must-see attractions with my mom and grandma. It was a special trip I will always remember.
We departed from busy Chicago Midway International Airport on Holy Thursday afternoon. Our luxurious hotel was in the Seaport district. We hit the ground running while exploring that part of town which was one block from the World Trade Center T-stop (public train/bus transportation). It was a great discovery, and we proceeded to take the T every day on our trip while traveling like the natives. We stumbled upon a delicious Mexican restaurant, Rosa Mexicano. My mom, grandma and I agreed it was the best authentic Mexican food we ever had.
Good Friday was a spectacular day! We bought tickets to see the Red Sox play on opening day. We walked around Boston and geared up to visit iconic Fenway Park for a glorious day of baseball. My experience at Fenway was unlike any other sporting event I have ever witnessed or been a part of. The genuine, diehard fans were so excited and rooted for their home team as the Red Sox beat the Padres in this thrilling home opener. I admired the loyal fans who cheered on their hometown heroes from the start of the game through the ninth inning. I enjoyed interacting with native Bostonians, while hearing stories of some who have attended 42 or more opening days at Fenway. We walked around the historic ballpark while taking in the sights and sounds of a storied Boston landmark. The vibes were awesome, and we took lots of pictures to remember the scene of my first trip to Fenway on this very monumental day.
I watched every episode of Cheers and remembered one of the most successful sitcoms starring south side legend, George Wendt. After the game, we walked through Boston Common and Boston Garden to enjoy a dinner at Cheers. It was a reminiscent experience to sit in the place where Norm, Diane, Sam, Coach, Cliff, and Carla spent numerous years laughing and providing entertainment for fans everywhere. I enjoyed my time at Cheers “where everybody knows your name!”
Saturday was jam-packed and full of history. We walked over 20,000 steps while taking in the famous Freedom Trail. We stopped at notable historic sites including Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, Benjamin Franklin Statue, Old South Meeting House, Old State House, Boston Massacre Site, Feneuil Hall, Paul Revere House, Old North Church, USS Constitution and Bunker Hill Monument among others. As we followed the red brick cobblestone path, I was reminded about moments of history that have been discussed in classes during my life. It was surreal to follow the trail and recall key leaders of our country and remember the start of the American Revolution. The Freedom Trail was even more special as we celebrate the 250th anniversary of the signing of the Declaration of Independence in 2026. As college basketball fanatics, we were sure to stop in at a few local establishments to catch the Final Four with UConn beating Illinois in a close game and Michigan winning big over Arizona.
We attended Easter Sunday Mass at Saint Leonard of Port Maurice Parish. We discovered this beautiful church on Saturday while strolling through town. The picturesque Peace Garden on the grounds caught our eye. While visiting the garden, we talked with a parish volunteer who shared information about the church. We learned that Saint Leonard was the first Roman Catholic church in New England built by Italian immigrants. Inside this breathtaking church were many statues and shrines including Saint Patrick.
We stopped at Modern Pastry Shop to sample some baked goods on our way to mass at Saint Leonard. The sweet treats did not disappoint. We headed toward the water after mass to take in the city’s scenery on a Boston Duck Tour. Our tour guide, Professor Quackenstein, was exceptional. He was unbelievably knowledgeable about Boston history and all that the city has to offer. We started out on land traveling around the city and then took the plunge into the water to gain a new perspective. It was an experience unlike any other and unique to the magnificent city of Boston.
We enjoyed an authentic Italian dinner in the North End before hopping on the T to Cambridge. We wandered around Cambridge and took in the views of prestigious Harvard University and the surrounding neighborhood. I enjoyed some delicious Ben and Jerry’s ice cream from Vermont as we explored the set of Good Will Hunting.
Monday was our final day in town. We headed out early to make the most of our day. We took the T to the Boston Public Library. The building was stunning with art and artifacts dating back centuries. I enjoyed looking at old books and took some photos of books to check-out in the future. The library was historic on one side and a typical, user-friendly space on the other side, complete with adult and children’s sections and areas for a variety of interests. We visited some ancient historic churches referenced on our Duck Tour before hopping on the T.
Our last Boston destination was the John F. Kennedy Presidential Library and Museum. The building was beautiful and set on the Atlantic Ocean, as President Kennedy loved the water. I enjoyed watching videos and learning more about this charismatic, youthful 35th president of the United States. This legendary place houses authentic clothing, letters, furniture, gifts and so much more history that represents a progressive time in our country. After exploring for a few hours, we rode the T back to the North End to enjoy a delicious dinner (recommended by locals) before heading back to pick up our luggage and depart for home.
My phenomenal trip to Boston was filled with forever memories made with my mom and grandma while exploring a city I will definitely visit again! I spent the rest of spring break playing lacrosse, caddying, and relaxing while enjoying time with my family and friends.








