14 Unique and Non-Touristy Things to Do in Boston
Enjoying the city views from my kayak on the Charles
Boston has been my home for over a decade, so I like to think that I am at least a decent authority on what to see and do in this city. I created this list, as I was tired of seeing the same places recommended over and over in all of the Boston travel guides. Yes, the Freedom Trail is worth walking. Yes, Beacon Hill is picturesque. Yes, our museums are excellent. And yes, Fenway is not to be missed. But there is so much more to my hometown than these greatest hits, and if you’ll come with me (a.k.a., scroll down), I shall endeavor to acquaint you with some lesser known (but no less worthwhile) things to do in Boston.
1. Kayak or Canoe on the Charles
It is one thing to see the Charles, the river that winds through Boston, but it is another thing entirely to be on it. Canoeing or kayaking on the Charles offers a fun and unique way to see the city – plus, it provides a great arm workout.
Paddle Boston has numerous rental locations throughout the greater Boston area, but if you’re looking for city views, I’d recommend either the Allston/Brighton or Cambridge location.
2. Stroll down the Esplanade
If water sports aren’t your thing, fear not, for you can still enjoy the Charles on land. The Charles River Esplanade, or Esplanade for short, is a park that runs along the bank of the Charles on the Boston side from the Boston University (BU) Bridge to the Museum of Science (a distance of about three miles). It boasts beautiful views and is also home to the Hatch Shell, where the Boston Pops holds its annual July 4th Fireworks Spectacular concert.
3. Visit the City’s Many Independent Bookstores
Boston is home to a vibrant community of indie booksellers. From the aesthetically pleasing Beacon Hill Books and Café to the romance-focused Lovestruck Books to Brattle Book Shop and its iconic summer sidewalk sale, there is a bookshop for everyone in Boston.
I created a list of several of my favorite Boston-area bookstores, and I recently wrote a follow-up post with even more bookstore recs.
The glorious summer sidewalk sale at Brattle Book Shop
4. Catch a Retro Movie at Coolidge Corner Theatre
I love Coolidge Corner Theatre. It is hands-down my favorite theater in the area. What sets it apart from other cinemas is its screening of retro movies. I have seen Sleepless in Seattle, The Thing, When Harry Met Sally, The Exorcist, Escape from New York, City Lights, and countless other classics here. If you’re a night owl, head here on a Friday or Saturday night at midnight to watch some of the finest B-grade movies out there.
5. Explore the Boston Harbor Islands
Visitors to Boston are often unaware that it is home to 30 islands. Granted, some are off-limits to the public and only four are accessible by ferry, but those that are open to the public are worth visiting. The islands offer a slice of nature in an otherwise urban landscape, and the boat rides out to the islands provide second-to-none views of the Boston skyline.
6. Visit Castle Island
Castle Island is an island in name only; it has been connected to the mainland since 1928. A more apropos name would be Castle Peninsula, but that doesn’t have quite the same ring to it, does it?
Castle Island is most famous for Fort Independence, a 19th-century, pentagonal fort, but there is more to the “island” than its historic fort. You can go for a stroll along the Harborwalk and Head Island Causeway, which offer not only gorgeous ocean views but also unparalleled plane watching. If you feel up to braving the cold New England waters, you can go for a swim at Pleasure Bay Beach. Regardless of what you do, though, you must stop at Sullivan’s, a Boston institution that serves up tasty fast-casual fare. My go-to order is the baked haddock with rice and a raspberry lime rickey, a quintessential summer drink here in New England.
Spectacle Island. Hard to believe this is only a 30-minute ferry ride away from Boston.
7. Behold the Stunning Art and Architecture of the Boston Public Library
The Boston Public Library on Boylston Street is somewhere that I always recommend to people visiting the city. It features breathtaking architecture and artwork, including murals by John Singer Sargent. Plus, it is completely free to visit, and when you’re traveling, every penny counts.
8. Try Your Hand at Candlepin Bowling
Unless you’re from New England, you’ve likely never heard of candlepin bowling. It’s a style of bowling that uses small, handheld-size balls and narrow pins that resemble, well, candles. If you’ve never tried it, I highly recommend giving it a go before you leave New England. There are several bowling alleys in and around Boston that specialize in candlepin bowling. I’ve been to American Flatbread, and what’s nice about them is that they are not only a bowling alley but also a full-fledged (and actually good) restaurant. And yes, you can eat at the lanes. If you want to go there, I’d recommend making a reservation ahead of time, as it’s a popular spot.
9. Walk (a Portion of) the Boston Harborwalk
The Harborwalk is a 43-mile public walkway that traces Boston’s shoreline from Dorchester up to East Boston (or as us locals affectionately call it, Eastie). My favorite part of the pathway is in the Seaport, specifically the portion near Fan Pier Park. From this section of the Harborwalk, you have an amazing view of the Boston skyline – it makes for the perfect photo backdrop.
Bates Hall inside Boston Public Library
10. Attend a BSO Performance
The Boston Symphony Orchestra (BSO) is one of the “Big Five” American symphonies, and they frequently play host to renowned soloists, including Hilary Hahn and Yo-Yo Ma. Regardless of whether you consider yourself a fan of classical music, you should attend a BSO concert if you can; it will be an unforgettable experience.
11. Take the T or Bus (or Drive, If You Dare) to Harvard Square
In addition to its namesake, Harvard Square boasts a ton of shops and delicious eateries. It’s home to Lovestruck Books, which I mentioned earlier, and Felipe’s, one of my favorite spots for tacos in the Boston area.
12. Also Take the T or Bus to Union Square
Located in Somerville, Union Square is chock-full of trendy restaurants and cafés. There’s Union Square Donuts, which serves up some of the best donuts in the city. Bloc Café is a cool, laidback café located in a former bank; the old vault has been converted into a sitting area. There’s also Machu Picchu, Juliet, and so many other amazing restaurants. And then there’s Bow Market, which has even more food spots as well as shops, including the cozy and well-curated Side Quest Books and Games.
Mount Auburn Cemtery
13. Check out a Feast in the North End
Every August, the North End plays host to several multi-day festivals known as feasts. Each feast honors a different saint or martyr and features a procession, music, and food – lots and lots of food. My favorite feast is Saint Anthony’s, which is usually toward the end of August. It tends to be the largest of the feasts and consequently has the greatest variety of vendors. Be sure to try an arancini!
14. Visit Mount Auburn Cemetery
I know what you’re thinking – a cemetery, really? But Mount Auburn is no ordinary cemetery, it is the first landscaped cemetery in the country. Its 175 acres abound with trees and flora, making it an ideal spot for birdwatching or simply reconnecting with nature. Climb the Washington Tower for panoramic views of the surrounding area, including the Boston skyline. Please note that Mount Auburn is an active cemetery, and as is the case when visiting any cemetery, active or not, please be respectful (e.g., be quiet, stay on the designated pathways, etc.).
And that’s a wrap! I hope you enjoy your time in Boston, and if you have any questions, please feel free to ask them in the comments section below!
And if you’re looking for more Boston travel inspiration, peruse my past Boston posts.
-Julia
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