I’ve been living in Boston for school for almost four years now, and it’s been a goal of mine to explore the city and its many unique neighborhoods. Being a student with classes, clubs and activities (and sometimes working a full-time job), it can be hard to set aside time for leisure, let alone full-on excursions or day trips. Oftentimes, I revisit the same sites repeatedly because I rarely take the time to discover new things to do. Because I have a chronic routine, I rarely take the time to discover new things to do. As one can probably decipher, this leads to little new finds of places to go and things to do.
This past summer, I decided to take a more active approach to my Boston journeys and take the time to write out a bucket list, not as a be-all and end-all to my leisure time, but as an opportunity to be more intentional about how I spend it. In July and August, I enjoyed a free concert in the Boston Public Library courtyard, visited the Isabella Stewart Gardner Museum, took a day trip to thrift in Somerville and even had a beach day in Rhode Island with my cousins!
So, to inspire your own Boston fall bucket list, or to even give you a few overlooked ideas you may have missed in the chaos of living in a big city, here are a few things on my list I’d personally like to do as the leaves start to change and the weather gets just a bit chillier.
- Celebrate Oktoberfest
I’m German, and I’ve never celebrated Oktoberfest?! Boston.com recently published an article on where to celebrate Oktoberfest in Greater Boston, and I will certainly be checking out their list. Oktoberfest runs from Sept. 21 to Oct. 6 and breweries all over the city hold events to celebrate.
- Walk (Or Run) Through Arnold Arboretum in Jamaica Plain
Jamaica Plain is one of Boston’s most beautiful neighborhoods, with large green spaces and many natural gathering spaces for community members. The Arnold Arboretum has over 200 acres of landscape, and I would love to take a walk or run through the accessible paths to go leaf-peeping.
- Somerville Flea in Davis Square
The Somerville Flea is a vintage and artisan market in Davis Square. Located on the corner of Holland St. and Buena Vista Rd., it is open Sundays from 10:00 a.m to 4:00 p.m. until Oct. 27. I’m always looking for new vintage markets, so this is a perfect option to explore (and another opportunity to visit Somerville again)!
- Eat at Zaftigs in Brookline
Brookline, more specifically Coolidge Corner, is one of my favorite surrounding neighborhoods in Boston. There’s plenty to do there to fill a day, and obviously, sustenance is the key to having a fulfilling day. My personal favorite is Kupel’s Bakery, but I’ve been dying to try out Zaftigs Delicatessen, which serves Jewish cuisine. My friends have gone numerous times, and I want to make it a priority to make it out there in the next month or two.
- Attend a Trivia Night
As a newly 21-year-old, I’m not only discovering bars for their drinks but also for their other charms. While I may not be a trivia guru, it’s a fun activity to do with friends that’s a little more low-key. Penguin Pizza in Mission Hill has trivia on Wednesdays, and they even give out prizes. I hear they also do drink pitchers, which is another plus. Another local bar is Puddingstones on Tremont St. On Saturdays, they have trivia night at 7:00 p.m. and the added amenity of an outdoor patio.
- Boston Lights at Franklin Park
From August through October, the Boston Lights show at the Franklin Park Zoo lights up Dorchester with immersive walk-through displays of animals, flora and other enchanting scenery. It may be geared towards kids, but I’ll never pass up an opportunity to satisfy my inner child. There are also nightly Chinese classical dances, which are super cool. Starting Oct. 1, the show is open from 5:00 pm to 10:30 p.m., and college students save $7 on admission on Tuesdays and Wednesdays.
- Visit Salem
It’s a crime that I haven’t visited Salem during spooky season yet. It’s a classic trip, given the significance of the Salem Witch Trials. The MBTA Commuter Rail makes the trip easy, especially without the stress of parking a car. I’m looking to visit at the beginning of October before it gets super busy, but I think the crowds of tourists are a part of the experience.
- Watch the Sunset on the Esplanade
This is another classic Boston activity that becomes less appealing as the weather gets colder. Before the chill is too much to bear, however, I’d like to spend one more night watching the sunset along the Charles River. The sun is now setting around 6:30 p.m. (so early, I know!), so I’ll have to go right after work, but it’s a great place to meet up with friends, bring snacks and hang out.
- Escape Room
This one is a bit random, but it’s an activity one of my friends has been suggesting for months now. Not only is it a great indoor activity for a rainy day, but I also see it as something to strengthen my friendships; hey, if we can get through screaming at each other to decipher clues and uncover the mystery, I think our relationship can overcome anything. I’ve been looking at Escape the Room Boston and Trapology Boston, both located downtown.
- Solo Museum of Fine Arts Trip
The Museum of Fine Arts is another iconic location in Boston. As a university student, I get in for free, and you better believe I will take advantage of that. In the past three months. I’ve taken two solo trips to the museum, each trip dedicated to a different wing of the building. I’ve also taken some time to read and enjoy the Calderwood Courtyard while the weather is still nice. It’s also a great activity to do alone and on days when the weather isn’t as nice.
- Visit An Apple Orchard Outside of Boston + Eat Apple Cider Donuts
I love apple orchards, and apple cider donuts are my absolute favorite fall treat. It was a childhood tradition to go apple picking, and even though home is just two hours away in Connecticut, it’s very nostalgic to me. I’ve got another list from Boston.com — this time, their readers’ top choices for apple picking (though I’m still waiting for the updated 2024 list). I went to Honey Pot Hill Orchards last year, which is widely considered one of the best orchards in New England, and I’d love to make the trip again. There’s a hayride, a maze, apple picking (of course) and an amazing shop with freshly made apple cider doughnuts and other treats.
While I’d love to cross off everything on this list, I know that my weeks get busy, and it’s alright if I don’t “accomplish” everything. I may not see every nook and cranny of Boston, but I do know that I’ll have taken more charge of my leisure time, and that’s good enough for me.