5 Unique Things to Do in Boston This Fall

By Marianna Gavurmadzhyan

Photo by Emma Almaraz

Boston is a city that shines in every season, but fall might be when it feels most alive. The last tendrils of brilliant weather, beautiful foliage and rush of students returning to campus make autumn here unlike anywhere else. While you could always grab a pumpkin spice latte and wander Beacon Hill, there are plenty of other ways to experience the city this season. Here are five activities that capture Boston’s distinctive fall charm.

1. Pumpkin Painting on the Esplanade

Carving pumpkins is a classic way to kick off fall, but it’s messy and rots before you can blink. Instead, grab a pumpkin and paint it along the Charles River Esplanade on one of the many docks or tables. The riverside paths, framed by red and golden leaves, create the perfect autumn backdrop as students, families and locals gather to enjoy the walkway and all it has to offer. It’s an easy, festive way to celebrate the season, and you’ll leave with your own handmade fall decoration.

2. Watch the Head of the Charles Regatta

Every October, the Charles River hosts one of the world's largest three-day rowing competitions, the Head of the Charles Regatta. And it’s not just for rowing fans. The event turns the riverbanks into a festival, complete with food stalls, live commentary and cheering crowds. Whether you’re there for the athleticism or just the lively atmosphere, it’s a classic Boston fall tradition you won’t find anywhere else. You’re especially lucky if your school is located right by the river, giving you and your friends a front row seat!

3. Explore the Arnold Arboretum’s Autumn Foliage

Harvard University’s Arnold Arboretum in Jamaica Plain is a must-visit year-round, but what makes it special in the fall is the colorful foliage. Beyond wandering the sprawling paths lined with vibrant maples and oaks, the Arboretum features seasonal activities like guided foliage tours and nature walks. Its collection of rare trees make the colors even more impressive than a typical city park stroll. Many people go toVermont or New Hampshire, not realizing the Arboretum has everything and more only a few miles away. 

4. Visit the Mapparium at the Mary Baker Eddy Library

Step off the beaten path and into a three-story, stained-glass globe. The Mapparium is a massive glass globe that you can actually walk inside of, making it one of Boston’s most unique gems. In the fall, the crisp air outside makes ducking into this warm, glowing installation even more magical and cozy. It’s both educational and whimsical, offering a unique perspective on how the world looked in 1935, frozen in time in luminous glass.

5. Take a Ghostly Beacon Hill Lantern Tour

Sure, ghost tours exist in every historic city, but Boston’s lantern-lit walks through Beacon Hill have their own special charm. The narrow, gaslit streets lined with Federal-style brick townhouses look straight out of the 1800s. Add in eerie stories of Revolutionary-era spirits and mysterious apparitions, and you’ve got a fall evening activity that feels both atmospheric and chilling.

Fall in Boston is more than a ticking time bomb to six months of frozen paths and rain; it’s about finding experiences that mix history, community and creativity. From cheering on world-class rowers to painting pumpkins on the Charles, the season here offers activities that feel uniquely Boston. So grab a cozy sweater, gather your friends and dive into autumn the Boston way.