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Guide to the Perfect Fall Day in Boston

This article is written by a student writer from the Her Campus at Holy Cross chapter.

Last weekend my friends and I ventured into Boston for the day and it was the perfect way to get off campus and enjoy the beautiful fall weather. We spent a while creating our itinerary for the day because we wanted to get the most out of our trip, since we don’t get the chance to visit Boston that often. Here is our itinerary and some of my recommendations for the perfect fall day!

  1. Brunch

First, we stopped for Brunch at Sonsie on Newbury Street after getting off the train at Back Bay. The view of Newbury Street creates the perfect ambiance for brunch while the inside of the restaurant has a cozy and elegant feel. The service and food were great, we had no complaints! 

  1. Shopping on Newbury Street

In my mind, no trip to Boston is complete without shopping. Newbury Street spans eight blocks of luxury stores, small boutiques, quaint coffee shops, charming restaurants, and more. Some of my favorite stores we stopped into include Glossier, Zara, Brandy Melville, and Anthropologie. In the midst of our shopping, we passed by the famous Levain Bakery and picked up a mid-day sweet treat, and I can confirm that the hype is definitely worth it. Before heading to our next destination, and in desperate need of caffeine, we got lattes from Blue Bottle Coffee, and while Newbury Street boasts a variety of different coffee shops, this one seems to be the best for true coffee lovers. 

  1. Walking through the Boston Public Garden

 The Boston Public Garden is America’s first botanical garden. The leaves were just starting to change colors and there was a crisp, refreshing breeze in the air. The pathways are perfect to walk along and provide a break from the hustle and bustle of the city. While walking through the park, we saw students studying, families having picnics, and even a group of bridesmaids taking wedding photos. It’s definitely a must-visit on my list, especially after shopping for hours, since the peaceful and serene atmosphere provides a place to wind down and relax. 

  1. Beacon Hill

Our last stop was Beacon Hill, one of Boston’s oldest and most charming neighborhoods characterized by its cobblestone streets, brick houses, and rich history. We found ourselves wandering into Beacon Hill Books & Cafe, which spans multiple floors within a historic townhouse. The bookstore definitely captures the authentic feel and charm of Beacon Hill, which was once home to many notable writers like Sylvia Plath, Robert Frost, and Louisa May Alcott. Before walking back to the train station, we made sure to take a photo of Acorn Street, which is known to be one of the most photographed streets in the city. 

We ended our day by grabbing a quick dinner near the train station and headed back to Worcester for the night. This short trip was a much-needed escape from campus and a chance to get to know Boston a little better. I’ve only been to Boston a handful of times, but each time I seem to appreciate the beauty and culture of the city more, especially during the fall.

Lauren Piacentine

Holy Cross '27

My name is Lauren Piacentine and I am currently a sophomore at Holy Cross. I am majoring in English and Psychology on the pre-law track. I am from Newark, Delaware and I enjoy traveling, going to the gym, reading, and being around my family and friends. I am super excited for my first year writing for HerCampus!