Ever since I was a kid, I always assumed that the moment I saw Boston, I would immediately want to live there. This very much proved to be true. New York and Chicago were amazing and I’m sure I’d be more than happy in either place, but Boston is totally my jam, and I think if I could live in any city in the United States, that’s where I would go. It looks and feels beautiful in the autumn, the streets feel very safe, there are so many historical buildings and gorgeous houses, and with all the big colleges and universities in the area, you’re just surrounded by intelligence and academia. I fell in love!
Here’s how we spent our long weekend.
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Cabot Estate
We started right in the Cabot Estate neighborhood where we were staying in Jamaica Plain. This is a private condominium association on historic grounds with a castle right inside! The hosts we were visiting are absolutely delightful old friends of my fiance’s family, and they gave us a tour of the grounds and the old Victorian-style manor.
If there was a castle in my neighborhood, you’d never be able to keep me out of there. I’d be in there with a book at all hours.
Jamaica Plain is also just a really nice area with beautiful houses everywhere. We had fun just driving around and looking at them all.
Jamaica Pond
Cabot Estate is right across the street from Jamaica Pond, which is surrounded by a fantastic park where people train for the Boston Marathon, designed by Frederick Law Olmsted. (I’m always amazed to see how much he got around in his day! I’ve noticed his name cropping up ever since reading The Devil in the White City. I’ve seen it in New York at Central Park and the Met, various parts of Chicago, in Asheville at the Biltmore, and now in Boston.)
Boston University Castle (Dahod Family Alumni Center)
We got to take a tour here because it was one of our favorite potential wedding venues. (We ultimately ended up going with Rhodes Hall in Atlanta because it was similar while being more accommodating and overall the simpler option. But we still loved walking around here.)
Libraries
Boston is home to some magnificent libraries. We of course had to check out the Boston Public Library and the Boston Athenaeum.
Boston Common
The Boston Common is the oldest public park in the United States.
We have a joke where I look at every single statue in Boston and say, “Is that Paul Revere?” because I did it once and it wasn’t and we for some reason found this hilarious. So behold: Paul Revere.
Acorn Street
We had to stop by the most photographed street in the United States.
Isabella Stewart Gardner Museum
I immediately connected with this place, an idyll composed by a woman who just wanted to travel and surround herself with beauty and to share it with the world. Gardner traveled the world and collected her favorite art pieces and placed them throughout her home, which she opened to visitors. I also love that although they have had recent issues with theft (paintings have been cut out of their frames and removed from the building), they are committed to maintaining Isabella’s vision and have left those frames in place. (And hopefully they’ve gotten better security!)
Baleia
We had a wonderful time at Baleia, a seafood-forward, Portuguese-inspired restaurant with such a fun atmosphere. To start, we tried some cocktails. I had their Viuvo (Laird’s apple brandy, brown butter, celery root, Yellow Chartreuse, and Peychaud’s) and Castelo Rodrigo (Eagle Rare 10-year bourbon, sweet vermouth, CRF brandy, maraschino, Licor Beirao, and cracked pepper). Then we shared plates of Portuguese sweet rolls with chamomile butter; octopus carpaccio with crispy potato, pimenta aioli, and Moroccan black olive; grilled mushrooms with harissa, charred onion yogurt, and fried shallot; and a whole roasted fish with charred lemon, presunto, and anchovy that my fiance still says is the best fish he has ever eaten in his life.
Tours
The Freedom Trail Tour is really fun and covers a lot of ground on foot. So if you love to walk and want some close-up views of Boston history, this is definitely the way to do it. If you’re looking for something more relaxing that gets you a broader view of the city (and if you’d like to experience riding Michael-Scott-style from the road right into the water and back again), you might prefer a duck boat tour! Or if you’re like us and want to learn as much as you can, try both! You’ll learn and see different things on each.
Commonwealth Books & Old Prints
This cozy little place was so nestled away that we almost missed it completely. We just happened to catch a glimpse of it down an alley while on the Freedom Trail Tour and knew we had to go back. It’s a top-notch used bookstore that reminded us of Jacksonville’s own Chamblin.
James Hook & Co.
About a decade ago in Jacksonville, food trucks had a bit of a movement. So when I tried my first lobster roll out of one and found it an exceedingly disappointing experience (a loaf of hard, dry bread with a tiny smudge of lobster flakes in the middle), I just assumed I hated lobster rolls. I thought that for years and years until we went to Boston and I dared to believe everyone who told me my bad experience was not indicative of the true nature of lobster rolls. I’m so glad I did. That thick, toasty, buttery bread, absolutely overflowing with delicious, huge chunks of lobster, cost us $30, and I only got half of it. But I was ready to go back and buy a second one and eat the entire thing myself, had we not been in a hurry. I highly recommend James Hook‘s lobster rolls. Clam chowder, too.
Beacon Hill Books
This was such a charming shop. With four floors, all sorts of cute and cozy little nooks, and toy trains running around, it had so much character and whimsy. Definitely one of my favorite shops I’ve ever been inside. There was a whole subset of the fantasy section titled “Other Worlds” that I wanted to stand in front of all day, until I was diverted by the “Aesthetics” section and went to go look at interior design. It was also cool to discover and learn about Persephone Books!
Beacon Hill Chocolates
Loved this place. Check out my review!
Harvard
The original gated section of Harvard is gorgeous, albeit fairly small.
Don’t get me wrong. In no way am I turning up my nose at Harvard; I would never. But from an architectural/design standpoint, I was not as impressed with the campus layout as I expected to be, especially having just visited Dartmouth a year earlier, which had a bigger overall footprint. Outside of this original section were sprawling buildings that looked like they were from the ’70s. I wish they’d taken the opportunity to maintain the integrity of the original design as they expanded, rather than putting up cheap, bland structures.
Harvard Museum of Natural History
We had a great time in here! Although we were rushed somewhat (it seems there’s never enough time to go through a museum at the pace you’d really like to), we got to see so much cool stuff. I could have spent hours just in the geological section, but then we would never have gotten to see the amazing taxidermy.
Nubar
When we finished our stroll through Harvard and the museum, we were famished. We were also freezing and so worn out and needed to get someplace warm. We found Nubar inside the nearby Sheraton, which had a great cocktail list. I had what they called a “Pumpkin’s Patch” (I still don’t understand the apostrophe-S in the name)–Brinley’s Shipwreck Spiced Rum, Bailey’s Pumpkin Spice Liqueur, and sweet pepitas. It was delicious. I no longer recall what I had for dinner, but that was probably due to the trauma that has stuck with me. (To be clear, this was through no fault of the restaurant.)
As we were eating and relaxing, an older gentleman across the restaurant from us passed out in his chair. I’m not sure exactly what happened; I heard a shout–“Is there a doctor? We need a doctor over here!”–and looked over as he was turning grey, his eyes were rolling back in his head, his mouth had fallen open, and his chair was tipping backwards, with him landing on his back on the floor. I legitimately thought the man had just met his end right in front of me and was so disturbed by it that I started to shake and cry right there at the table. (I was still dealing with a fairly recent loss at this point and was still a bit of a mess.) Fortunately, he was still breathing, and EMTs quickly came for him, carrying him out right past us. I don’t know what happened, but I am hoping he is okay.
We were both somewhat shaken, having just had a friend pass out in front of us at a party only a week before. While certainly not a highlight of our trip, it was something that stuck with us that season.
Other Views
Bonus: Book List
These books don’t all have to do with Boston, but here’s a list of every book cover I photographed while we were there. (I do this frequently so I can remember to add the book to my reading list later.)
- Black River Orchard, by Chuck Wendig
- Boston in the Golden Age of Spiritualism, by Dee Morris
- Chasing Beauty, by Natalie Dykstra
- The Little Ghost Who Was a Quilt, by Riel Nason
- Magic, by Chris Gosden
- The Wager, by David Grann
- The Provincial Lady Series, by E. M. Delafield
- The Fortnight in September, by R. C. Sherriff
- Gardener’s Nightcap, by Muriel Stuart
- Miss Pettigrew Lives for a Day, by Winifred Watson
- Mariana, by Monica Dickens
- The Upside-Down World, by Benjamin Moser
If you liked this post, you may enjoy my previous stop in Boston as part of an autumn road trip through parts of New England, or this guide to another autumn road trip through Virginia.
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