Summer’s here, and that means pulling together a summer bucket list of things that we really want to do this season. Mine’s Boston-specific, and I’m raring to go! I have some exciting related personal news to share—read to the end to find out! Follow along with me this summer on Instagram and Facebook, and create your own Summer Bucket List with a FREE Instagram stories template!

My Boston Bucket List for summer 2022

Tis the season for summer bucket lists to start cropping up—I don’t know about you, but I’ve seen them all over the place. From the hugely ambitious to the gentle reminder, these lists capture what would make us feel good about our fleeting summers.  This year, I’ve created a Boston Bucket List for highlights I want to hit in and around the city (for these purposes, I’m including Cambridge, Somerville, and Brookline).

Keep reading to find out why I’m focusing my list on Boston this year—it’s exciting!

Why a bucket list?

The term “bucket list” doesn’t exactly have great connotations, it being things we want to do before we kick the proverbial bucket, but perhaps the prospect of death motivates us? Really, though, I think most of us use the term as a fun way to state our goals and to have something to work toward. I’m certainly not thinking about death with my Boston Bucket List!

I am, however, thinking that summer doesn’t last long, and I can get caught up in the day-to-day and miss things that I’d really wanted to do. Also, given the last couple of summers, activities were limited, and some of these things weren’t even possibilities (or safe ones).

I’m missing that summer feeling, you know, when you have all the time in the world, and you’re just having fun. I thought by writing down and sharing my Boston Bucket List that I’d help ensure that I’d actually do the things!

Instagram Story Image of my Boston Bucket list for Summer 2022. Photo of the Boston Skyline from the Longfellow Bridge, with activities from my bucket list (Fenway Park, Shakespeare on the Common), etc.
My Boston Bucket List for Summer 2022

Follow along with me and make your own summer bucket list!

Will I actually do the things on my Boston Bucket List? Follow along and find out! I’ll post my progress on Instagram (@wonderandsundry) and Facebook, as well as What a Wonderful Week, which you can get delivered straight to your inbox each week by subscribing. Let’s make sure we’re connected!

Subscribing, by the way, gets you access to the Wonder & Sundry Guide to Boston, which I’ll update with findings from my Boston Bucket List, as well as other exclusive content (next up—a neighborhood guide).

And, since bucket lists are more fun with friends, I invite you to make your own Summer Bucket List that focuses on where you live. What fun things can you do around you that would make you feel like summer? Here’s a fun template you can use for your Instagram storiessubscribe for access!

My Boston Bucket List for summer 2022

My Boston Bucket List includes 14 awesome activities that I can’t wait to start! They are not in any particular order.

1. ICA Watershed

The Institute of Contemporary Art is one of my favorite museums in Boston, not only for it’s collection and rotating exhibitions, but also just for the building itself. Located on the Fan Pier in the Seaport District, the ICA sits right juts out over the waterfront giving visitors a gorgeous view of Boston Harbor.

Now the ICA has a seasonal installation in East Boston called the ICA Watershed. If you have a ticket to the museum, it entitles you to a ride in a water taxi (another Boston Boat Ride!) across the harbor to see the exhibit. This year’s group exhibition is called Revival: Materials and Monumental Forms and focuses on reclaimed materials.

A boat ride AND art? Yes, please!

Castle Island

2. Castle Island

Going to Castle Island is just good old-fashioned fun. On a hot day, locals head out to the island to check out Fort Independence, feast at Sully’s or cookout or picnic along the shore. It’s also a great place to watch planes take off from Logan Airport. My perfect Castle Island day involves finding a spot along the far side of the fort, looking out toward the Harbor Islands and having a lovely picnic and a read, followed by ice cream at Sully’s. It’s a bit of a pain to get to, but I’m always glad that I made the effort.

Bonus: A beer at Barking Crab once I’m back in Boston.

3. Stroll Beacon Hill and take photos

My maternal grandparents lived in Beacon Hill when they were first married. No, they were not rich; one side of the hill used to house working-class people. The whole hill is an exceedingly pleasant neighborhood.

It’s been a hot minute since I’ve wandered through Beacon Hill, and I miss it. I want to stroll leisurely through the area, snapping photos (including the lovely Acorn Street) before heading down to Charles Street for a snack or a glass of something nice.

Sadly, my connection to this view is no more

4. Roof deck bar/Observatory at sunset

I want a spectacular view of the city at sunset this summer. The Pru’s closed, so I’m looking elsewhere. Options include

  • The Envoy Hotel
  • Six West
  • Custom House Tower
  • Judson B. Coit Observatory (bonus—get to see the stars too!)

Suggestions welcome! I’m all ears!

Festival in the North End Saint parade, with crowd and brick buildings in the background. A festival in the North End is on my Boston Bucket List.
Boston's North End throws some great festivals

5. Attend festivals

The North End has some fantastic festivals, as do some other parts of the city, and I am going to at least one of them.

Somerville also features a number of summer festivals, including ArtBeat.

Arnold Arboreturm
The Arboretum in Spring

6. Go to all of the parks in the Emerald Necklace

Frederick Law Olmsted was born 200 years ago this year, and his Emerald Necklace in Boston, a series of six parks stretching over seven miles through Boston and Brookline and includes the Arboretum and  is a jewel of a system. It’s been a while since I’ve visited several of these parks, and I want to get reacquainted.

7. SoWa Open Market and a stroll through the South End

This area has several open markets now, but SoWa Open Market is the grand dame. With food, craft stalls, and artists, this market in Boston’s picturesque South End makes for a perfect Sunday stroll.

Boston Bucket List Fenway Park. Photo of baseball game at Fenway Park

8. Embrace my inner Bleacher Creature at Fenway Park

I’m going to a baseball game this summer. I’m going to root for the Sox, drink a beer, eat a Fenway Frank, and sing Sweet Caroline at the top of my lungs (not really—the lyrics to that song are super weird).

9. 4th of July Fireworks on the Mass Ave Bridge

I love watching the fireworks on the Mass Ave bridge, and it’s been way too long since I’ve done it, as I often head out of town that weekend. This year, I’m going to see the fireworks in person.

Boston Bucket List: Outdoor movie. Casablanca at the Boston Harbor Hotel outdoor movies by moonlight series. Humphrey Bogart in full frame
Catching an outdoor movie at the Boston Harbor Hotel

10. Outdoor movies

I have two things I absolutely must do in order for me to feel like it’s summer: watch Jaws and see an outdoor movie. Well, I get to do both in one go this year, because Jaws is showing outside for Movies by Moonlight. We are going to need a bigger bowl o’ popcorn! And possibly a ‘Gansett.

11. Films at the Brattle, Harvard Film Archive, Coolidge Corner, and the Somerville Theatre

Speaking of movies, catching films at Boston’s great theatres is a must for my Boston Bucket List. To me, nothing beats the heat like sitting in a chilly, dark theatre with a box of popcorn.

I’ve been to the Brattle since Covid, and I went to see DakhaBrakha at the Somerville Theatre, but I haven’t just gone to the movies. The Harvard Film Archive has an outstanding collection (and is within easy walking distance) and a great line up this summer (I love Fellini), and the Coolidge Corner Theatre puts on some great series (perhaps a midnight movie!).

12. Ride the trolley to Mattapan

This one is weird, but it’s been ages, and it’s really cute. I’m going to take the red line to Ashmont and then ride the trolley to Mattapan. And probably come back almost immediately—it’s a little dicey out that way. I haven’t ridden that trolley in twenty years, and it’s time. Credit to this TikTok for inspiring me.

13. Boston Athenaeum

On a rainy day, when I’m feeling contemplative, I’m going to buy a day pass to the Boston Athenaeum. I’ve always meant to visit this treasure, and I’ve never been. Onto the Boston Bucket List it goes.

14. Shakespeare on the Common

This is one of those things that I always mean to go to and most years miss, sometimes for good reasons and sometimes for lazy ones. This year, the play is Much Ado About Nothing, and I love the comedies, so I’m there!

Some personal news (aka Why I Made My Boston Bucket List)

I have a reason why I’ve made my Boston Bucket List for this summer, and why certain things are on it. This is my last summer in Boston for the time being. For reasons I’ll go into in other posts, I’ve made a very big decision: I’ve quit my job, and I’m going to go travel and write for a while, as well as test the waters for becoming one of those digital nomads we read so much about.

As this is my last summer here, I wanted to make sure that I hit the highlights. Of course, there’s plenty of other things I want to do, and I’ll be making special time for my dear ones, but these are things that I’ve truly loved about living here (and one I’ve always wanted to do), and I want to make sure that I experience them before I leave on my journey. Much more to come, and YOU are most definitely coming with!

What’s on your summer bucket list?

I’d love to hear what you’re planning to do this summer! Please share in the comments. To help, here’s a free guide. Subscribe to get it!