Things to Do in Boston
Boston is not only a visually stunning city, it is also home to the Red Socks, Beer and Lobster!

The city of Boston is one of my “second” homes. From historical battle fields, to Irish pubs, a mix of colonial and modern architecture, the fusion of blue collar values and lofty academics leaves me feeling relaxed and welcomed. The city is smaller than most capital cities and boasts a host of unique neighborhoods. It’s more intimate than it’s rival New York, and  it’s easy to escape for those dreaming of New England sea coast villages or the mountain wilderness of New Hampshire and Vermont.

Boston is where my mother’s family is from, where I went to school, it’s where all of my best friends live, it’s my first stop during any trip home, and it’s one of those places you could spend years exploring and never really figure it all out.

Bostonians are proud and loyal, with good reason. The city can lay claim to the nation’s oldest public park, first public library, first subway system, the first public school and as you will see everywhere the key role the city and its loyalists played in the American Revolution. I get asked over and over where to go and what to do in Boston. Here are 5 Uniquely Bostonian things you should do on your next visit to Boston.

The Freedom Trail

Boston Freedom Trail
The Old Boston State House

This is perhaps the most quintessential Boston tourist activity you can do. However, just because it’s popular doesn’t mean its not worth it. The Freedom Trail is a walking introduction to Colonial Revolutionary Boston. The trial brings walkers on a tour through the historic past of the city, covering 16 colonial sites over the course of 2-3 hours. The sites are connected by a red brick path serving as a guide through the city. At over 2.5 miles the trail combines museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.

You can take a self-guided tour or one of the many tours available through the Boston Common Visitors Center at 148 Tremont Street or the Bostix Booth located at Faneuil Hall. I prefer to walk, but you can also take trolleys that allow you to get on and off.

Oh, and stick around Faneuil Hall for some historic touristy shopping. Don’t forget to stop by my uncle’s bar, The Ames Plow Tavern for a beer and a reminder of what the area used to be like when it was an agricultural marketplace. Have a look at the bar and you’ll see pictures of my great grandfather and his blacksmith shop.

Fenway Red SoxCatch a Red Sox Game

Fenway park is not only the oldest baseball park in the United States, but the Boston Red Sox are the best baseball team. Well, OK, I might be slightly biased, but it is hard to imagin coming to Boston and not experiencing a night at Fenway. The fans are loyal (when we win), loud (all the time), and the sausages and beer are excellent (if overpriced). During and after the games is when you will get to the heart and soul of any Bostonian. Buy a ticket well in advance as games are almost always sold out, or test your luck with the scalpers lining the road to the stadium.

At the very least park yourself on a bar stool at one of the thousands of bars across the city during a game and you will see what true passion, and bitterness is all about.

North End

The North End is Boston’s oldest residential neighborhood with people living there since the 1630s. The area has gone through many face lifts and demographic shifts, from the wealthiest segment of Boston, to the first community of freed slaves, to mostly Irish, to a major Jewish center, and finally in the 20th century the center of the Italian American Community. If you are hungry this small 1/2 square mile area boasts over 100 small authentic Italian restaurants.

Your walk along the Freedom Trial will take you through the North End, so don’t forget to save room for Italian cannoli, a tour through the Old North Church and Paul Revere’s House.

Drink Beer

Sam Adams Brewery Tour

Beer, check. Beer, check. Beeeer, chick. bRRRR, hick...up

Ok, to be fair I would give this advice anywhere in the world. But Boston sports two of my favorite small scale breweries, Samuel Adams and Harpoon. These two classic American Breweries will have you laughing in the face of anyone who tries to convince you that American Beer taste like water. Rich in flavor, and steeped in history they will also knock you on your ass if you drink too many.

The Samuel Adams Brewery offers a tours with a tasting afterward for a suggested donation of $2. Tours run weekdays and weekends but fill up quickly and tickets are only available in person.  Harpoon Brewery has a free tasting on Weekdays and a $5 Weekend tour with a tasting afterward.

Eat Seafood

Nothing quite says New England cuisine like a large helping of seafood. From fresh lobsters, to New England Clam Chowder (psst that’s the white one), to raw oysters, you can not leave Boston without diving into the Atlantic ocean. You will find no end to places to eat lobster, which come boiled or steamed, with a fashionable plastic bib, drawn butter for dipping, a nutcracker for the claws and a pick for the legs. Eating lobster can be an expensive proposition and they are sold by the pound with market prices changing everyday. Personally, I’m a clam chowder and crab cake kind of a guy.

There are too many great fresh seafood restaurants to name them all. While my favorites are simple shacks in the small coastal towns near Boston, if you are in the city you can’t go wrong with Legal Sea Foods. Go to the one near Long Wharf and you can stroll along the water before or after dinner and watch the seals for free just outside of the Boston Aquarium.

Of course there is plenty of truly unique Bostonian adventures to be had in this culturally packed little city. We would love to hear your own recommendations.

Photo Credit 1, 2, 3, 4, 5

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30 Responses to “5 Unique Things to Do in Boston”

  1. The NVR GuysNo Gravatar says:

    Very cool! We were excited about the Freedom Trail and are now eager to check out the North End.
    The NVR Guys´s recent [type] ..Travelogue – on a mission in Washington DC

  2. LizNo Gravatar says:

    If you love beer and Boston then I totally recommend the Harpoon Brewery, its on the waterfront by the Convention Center, and has not only great beers, but a fantastic staff, and you can catch free tastings a lot of the time on the weekends!!

    Check out Charlestown too, its right over the bridge from the North End (is the end of the Freedom Trail) and has some great historic sites (USS Constitution, Bunker Hill Monument) and a lot of up and coming little restaurants.
    Liz´s recent [type] ..Photography Friday!

  3. Dave*No Gravatar says:

    Copley Square: Take tours of the Boston Public Library and Trinity Church, both of which are gorgeous inside.
    (The old part of the BPL, that is. The new part is concrete and nauseating florescent lights).

    Then leisurely stroll up Back Bay to the Public Gardens and take a ride on the Swan Boats.

  4. Beer and food!!! I think these two will be a great combination :D AND while watching a Red Sox game too!

  5. I love Boston but didn’t think to eat seafood there. I loved the historic cemeteries – it was pretty freaky to see names like John Hancock that I remembered from middle school history class. I couldn’t believe there wasn’t any sort of Boston tea party monument – but I hear that’s in the works?
    Scott – Quirky Travel Guy´s recent [type] ..Your guide to the Bonnaroo music festival

  6. The photo of the lobster is scary but I bet its very tasty too! Congrats to your inclusion in Aaron’s Friday Five Travel Blog Post, well deserved :)

    Awesome article, thanks Todd!
    Bocas Del Toro´s recent [type] ..Surfers Only – Isla Colon

  7. JeremyNo Gravatar says:

    I’ve never been to Boston. I’m looking forward to hopefully going sometime in the next year though. We are a bit closer now than where I was living before. Great tips!
    Jeremy´s recent [type] ..Italian Gelato in Florence – Tasting Tuscany

  8. Another great thing to do is hop on the red line (or walk across one of the beautiful bridges), and visit Cambridge. Harvard Square is lined with shops, musuems,historic buildings, restaurants – something for everyone.

  9. KristyNo Gravatar says:

    You had me at Beer. Oh and seafood. Would love to get to Boston someday!
    Kristy´s recent [type] ..Green Travel- Auroville India

  10. JillianNo Gravatar says:

    Drink beer. End of story!

  11. Renee KingNo Gravatar says:

    There’s something enchanting being in a city full of such amazing history. A definite must in my book.
    Renee King´s recent [type] ..The 12 of the best free apps that will make traveling a breeze!

  12. ReaseNo Gravatar says:

    I have never heard a bad thing about Boston. I definitely want to go!
    Rease´s recent [type] ..Attack of the Mexican Bee

  13. SabrinaNo Gravatar says:

    I really like your list! We were in Boston for a long weekend in 2009 and I really liked the city a lot. We didn’t drink a whole lot of beer nor did we catch a Red Sox game, but we did pretty much everything else on your list. We ate Italian food in the North end multiple times and had seafood close to the Long Wharf at the Barking Crab (I would totally recommend it!!). I think we walked most of the freedom trail too :) We also did a whale watch tour which was a lot of fun – except for the tour group of Asian kids whose stomach must have not been used to being on a boat. Disgusting! Except for that, totally fun!!
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  14. Great picks! I’d love to check out a Red Socks game, although as a New Yorker I’m a Mets fan :) Maybe I could see them crush the Yankees…
    Leslie (Downtown Traveler)´s recent [type] ..Alien invasion in the Lower East Side street art photo of the week

  15. CamNo Gravatar says:

    Did someone say Beer? Yes please!
    Cam´s recent [type] ..Photo Essay- Our Trip to the Dominican Republic

  16. WhitneyNo Gravatar says:

    Good things to do? Yes.
    UNIQUE? Absolutely not.

    Get off the freedom trail and on the beaten path, guys. There is so much more to Boston than this!

    • Todd WasselNo Gravatar says:

      Oh I don’t know Whitney, if you are a first time visitor to Boston I think the freedom trail is an excellent and uniquely boston thing to do. I don’t disagree that there is a ton more to do, but if your coming to Boston I think this is something that everyone should do.

  17. GlenNo Gravatar says:

    Hmmm…drink beer, eat seafood. 2 of my favorite things to do. And I agree, Boston is a great town.
    Glen´s recent [type] ..Behind the Scenes at the World’s Largest Aquarium

  18. RoxanneNo Gravatar says:

    You are triggering so many wonderful memories with this post. A meal in the North End is a must; all the pasta you can eat! Boston Tea Stop and Tealuxe in Harvard Square are among its lovelist offerings, as is Burdick’s Chocolaterie. A walk through Mt. Auburn cemetery in the spring is a beautiful end to a weekend.
    Roxanne´s recent [type] ..Chasing anemones and penmanship

  19. SusannaNo Gravatar says:

    Ooh, I like this post- I’d add:
    - window shopping and people watching on Newbury Street with a cone from Emack & Bolio’s, or take out from Snappy Sushi
    - strolling through Boston Common with some Richie’s Italian Ice (and going on the Swan Boats if you’ve got kids- or actually ice skating on the Frog Pond since it’s still winter, hmmm I guess you’d have to scrap the Italian Ice and ice cream ideas as well)
    - popping into Beantown Pub for a pint of Sam Adams and game of pool, or Silvertone’s for mac n’ cheese or either OmniParker hotel for some Boston Cream Pie
    - more window shopping and people watching- and eating at Faneuil Hall

    Dare I say I’m feeling a little homesick…and hungry! ;)

  20. Jeremy BNo Gravatar says:

    Great tips Todd! I’ve been to Boston a couple of times and it is definitely a fascinating city to visit. You will have to hold off on that Red Sox game for a month or so though. Also, I would recommend walking along the Charles River and check out Harvard as well. Beautiful area!
    Jeremy B´s recent [type] ..What is Budget Travel Adventures 10 ways it will help you travel

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