Two Years in Boston

I just finished packing up my apartment in Boston. I’ve lived in the city for the past two years — my first two years post undergrad — and it’s been incredible. Now, I’m sitting surrounded by cardboard UPS boxes, reflecting on my time here and preparing for a move to New York.

It occurred to me that I should make a list of my favorite things about Boston, especially while it’s still fresh. I figure it’ll be nice to look back on in a few years and, hopefully, it provides some good tips for anyone moving to the city.

1. Thinking Cup at 85 Newbury Street. I spent time here nearly every weekend, reading or writing while enjoying their cold brew. Each time, it felt like I’d discover a new detail about the place — the saxophone hanging under a subtle spotlight on the wall near the front; the old newspaper articles laminated into the tables; or how the walls are a slightly eclectic mix old exposed brick in the front, pristine white tiles behind the counter, and wood paneling in the back room.

2. Walks / runs / bike rides along the esplanade. A Boston classic.

3. Commonwealth Avenue at night in the winter. The median is lined with centuries-old trees, and the city hangs holiday lights along all of the branches. I saw probably a half dozen couples get engaged under the lights last year. Truly feels like a winter wonderland; pictures don’t do it justice.

4. Taking the Commuter Rail to Rockport. There are at least a dozen picturesque coastal New England towns easily accessible by train. I only discovered this my second year in Boston, and it’s a local secret I wish I had known sooner. Luckily, I had the common sense while in some of the small towns to buy some cool artwork (as mementos of how much I enjoyed those adventures).

5. Snowport in Seaport — Boston’s Christmas market. I found some cool artwork there, too.

6. When the fog would roll in over the harbor.

7. How easy it is to get to nature. A <60 minute drive will get you to the mountains; I definitely didn’t take advantage of this enough.

8. Beacon Hill in the Fall. Hard to imagine another neighborhood that feels like it was built specifically for that season.

9. The Museum of Fine Arts (I call it Boston’s mini Met).

10. That I could get from my doorstep in Back Bay to my gate in Boston Logan (airport) in <25 minutes. Huge.

11. Kayaking on the Charles — one of my favorite summertime weekend activities.

12. The way the snow sits on the Charles in the winter. Looked to me like something straight out of Station Eleven.

13. Biking along the beaches in Southie (South Boston) in the summer. I wouldn’t recommend swimming in those waters, but biking was perfect for catching the summer breeze and enjoying the view of the sailboats.

14. The rooftop at Felipe’s in the summer. 10x better when going with a group of friends, though.

15. Apple picking at orchards in northern Mass. My favorite was one called Boston Hill Farm. Pretty easy to get to with a little effort, and well worth the trek.

16. Little shops in the North End. A few months into living in Boston, a colleague gave me a tip that often, if you walked down some of the allies, you could find entrances to cute little shops run by Italian grandmas (I’m serious). It turned out to be true, and was a great tip.

There are, of course, many things I’m leaving out about my favorite parts of Boston. I made a lot of incredible memories with really awesome people. The best memories weren’t the type of thing one could put in a list, though. Lists are meant to be read, replicated, and repeated. So that’s what I put in this list: things I really enjoyed that I’d highly recommend to anyone else visiting the city — whether for a day, a week, a month, or a few years!