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12 essential activities for a weekend in Boston

12 essential activities for a weekend in Boston

I usually enjoy slow travel, but weekend trips are different.

The average week for me consists of working on my laptop from home or in local cafes, so by the weekend, I’m energetic enough to pack in a crapload of sightseeing.

When I decided to hit up Boston for a weekend, I did my usual research on things to do in the city. As an ex-travel agent, I consider myself pretty darn good at this, but this time I struggled to find any good info. Sure, there were some posts that outlined a few activities, but nothing that jumped out at me and said “here’s what you absolutely have to do in Boston”.

So, I decided to make my own ultimate list of activities.

HI Boston Hostel

HI Boston Hostel

HI Boston Hostel

I based myself at the HI Boston Hostel near Chinatown. It was seriously the perfect location from which to explore the city – it was an easy walk to 2 subway lines and had a bunch of cheap eats nearby.

As an eco-concious traveller, I was super impressed with the hostel’s green initiatives with recycling bins and power saving lights in every room. Plus, who could say no to warming up next to that cosy fireplace after a day of exploring in the cold?

Also, the rates include free breakfast. Nuff said.

So, here are my 12 essential activities for a weekend in Boston!


Beacon Hill, Boston

Beacon Hill, Boston

1. Beacon Hill

Beacon Hill has got to be one of the most adorable suburbs on the planet. Just look at these cobblestone streets and super cute doorways! I must have taken about a million photos in the hour we spent wandering around.

I followed the advice of Daisy from Simplicity Relished and walked along Chestnut Street and Acorn Street.

Boston Common

Boston Common

2. Boston Common

Boston Common is like the Central Park of Boston. It’s a huge grassy area where people hang out, and is especially nice in the summer. Lucky for me, it snowed on the weekend we were there so I had the pleasure of experiencing it in winter, too.

Boston Public Garden

3. Boston Public Garden

Right next to Boston Common is the Boston Public Garden. It includes a gorgeous lake where you can take a ride on a swan boat from April-September, and it has a super pretty bridge to walk across.

The Freedom Trail, Boston

4. The Freedom Trail

Yes, the Freedom Trail had to be included in this list. While the activity is touristy, you have to do it. No excuses.

The Freedom Trail is a self-guided walk that you can take through downtown Boston, and includes a bunch of historical sites. It starts at the visitor center in Boston Common and is marked by a red brick road. Here’s a map.

Note: The Freedom Trail is fairly long at 2.5 miles (4 km). If you’re not up for such a long walk, you can stop at Copp’s Hill Burying Ground, which makes it about half the length.

Quincy Market, Boston

5. Quincy Market

Apparently the locals avoid Quincy Market, but I thought it was really nice. It has some amazing food options for very reasonable prices and is situated in a beautiful old brick building. The food smells in this place will make you hungry, even if you just ate.

6. sample some Boston Cream Pie

Boston Cream Pie is technically a cake, but who cares – this cake/pie is filled with cream and topped with chocolate ganache.

You can get Boston Cream Pie at Quincy Marketplace, or at other bakeries throughout the city. I grabbed a slice at Cafe Bella Vita in Beacon Hill.

Boston Public Library

Boston Public Library

7. Boston Public Library

As a fan of architecture and photography, the Boston Public Library was one of my favourite activities on this weekend trip. The Library’s Reading Room and European-inspired interior courtyard were unbelievably photogenic! A 10 minute tram ride on the E line will get you to the library from downtown Boston.

Harvard University

Harvard University

8. Harvard University

What is arguably the most prestigious university in the country is an easy 15 minute subway ride on the Red line from downtown Boston. Even though I’ve toured Harvard before, it was still an interesting walk the second time around.

We downloaded the self-guided walking tour app off the Harvard website (which was not particularly clear or easy to follow), but you can also do guided tours of the campus run by students.

Museum of Fine Arts, Boston

9. Museum of Fine Arts

We had the Museum of Fine Arts recommended to us by some family members who had loved it, but the $25 entry fee was a bit hefty for our liking. I checked their website anyway to see if there were any sort of discounts, and whaddya know, it happened to be a holiday where the museum offered free entry to visitors!

If you’re not going to be there for a free entry day, the museum also does pay what you want on Wednesdays after 4PM. And if you’re not going to be there on a Wednesday, well, you still might want to pay the $25 admission fee because the museum is pretty damn good.

North End, Boston

10. Eat Italian food in North End

Boston has a huge Italian influence, and North End is where you’ll find most of it. The neighbourhood is super pretty and has a crazy number of Italian restaurants to choose from.

11. Go to an Irish Pub

One thing I’d discovered in my research was that Irish Pubs are popular in Boston. I picked the historic pub JJ Foley’s, and while it was a little more ‘sports bar’ than I expected, but it was still a great Boston experience. Their pub grub was also on point.

Boston Bowl

12. Go Candlepin Bowling

Candlepin bowling has weird cylinder shaped pins, but the gameplay is basically the same as ten-pin bowling. Boston is one of the only places where candlepin bowling is actually more common than regular bowling. You can find a list of lanes to test out your bowling skills here!

*I was a guest of HI Boston Hostel during my stay in Boston. I’m proud to be an honest and transparent blogger, so every opinion expressed on AGWT is a true review of my experience!


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Ashlea Wheeler

This post was written by Ashlea, a colourfully clothed and excitable vegetarian who loves photography and exploring the world. Find out more about me.

29 Responses to “12 essential activities for a weekend in Boston”

  1. Lindsay @ Frugal Frolicker

    Love this! I’ve been visiting my sister in Boston for years and we’ve made a point to do most of these things. Beacon Hill is our favorite! I’d also recommend sampling some clam chowder (I know this doesn’t apply to you, but to the non-veg Boston goers) and strolling along the Charles River when it’s a nice sunny day. Glad you finally got to see the snow! (And equally glad that I’m missing it! :P)

    Reply
    • Ashlea Wheeler

      Isn’t Beacon Hill just the best (especially when you’re snap happy like us)! I was seriously fawning over all the cute doors and shuttered windows 😀 You’re right about the clam chowder, I obviously didn’t try it but if you say that it’s good then it should definitely be on people’s Boston activities list!

      Bet you’re loving all the sun filled days in Aus 😉

      Reply
    • Ashlea Wheeler

      Thanks Daisy! I really loved Boston, especially the fact that it was so easy to walk around 😀 All the pretty buildings were so photogenic!

      Reply
    • Ashlea Wheeler

      Thanks Paul! Boston is such a lovely city, I’m really glad you enjoyed it as much as I did! I hope your next visit is just as good as the last one 😀

      Reply
  2. Mallory

    Boston looks so beautiful! My newest goals include traveling more within the US and Boston is at the top of my list right now. I haven’t had the chance to make it over there and I’m itching to, especially after seeing this post. This is a great roundup of places to go to and will be using this for my future planning!

    Reply
    • Ashlea Wheeler

      So glad you enjoyed the post, Mallory! Boston really is a lovely city and is well worth a visit. Kudos to you for making an effort to see more of the US, I think a lot of people don’t realise how many amazing places are right under their nose 🙂

      Reply
  3. Mary

    Great list! As someone who grew up in Boston, I think you covered it all. North End is my fave.

    Reply
  4. Maggy

    Thank you for this great post!
    I will travel to the US for the first time in my life in May and I am flying to Boston! After visiting friends in Maine, I will stay a few days in Boston before flying back home. I definetely check out some of the activities you listed. And I am glad you liked your hostel, because I already booked a room there too! 😀

    Reply
    • Ashlea Wheeler

      That’s fantastic, Maggy! I’m sure you will love your time in Maine and Boston. And I’m sure you’ll like the hostel too – I was very impressed with it!

      Reply
      • Maggy

        That’s great! I was impressed by the pictures and good reviews. And it was by far the cheapest option. 🙂

        Reply
  5. Nicole

    I’ve been to Boston only once when I was younger but didn’t hit even half of these wonderful things to see/do. If I may there is an amazing foodie guide I would love to share with those looking to pair this amazing guide with delicious budget restaurants in Boston! (Really looking forward to travelling to Boston soon!!) Any suggestions on where to stay? Then I think I’ll have everything covered!! 🙂

    Reply
    • Ashlea Wheeler

      You’ll definitely have to get back there, Nicole! As I mentioned in the post, I stayed at HI Boston which was a great base for exploring the city 🙂

      Reply
  6. sunny

    Hello Ashlea. I am Sunny from Taiwan and I found this post really great and helpful, and thus I am wondering if I would be allowed to translate it into Mandarin (traditional characters) and re-post it on my blog. In the beginning of my post, I wrote where the post was originally from and linked it to your blog, and I also mentioned that all the content, pictures and links are owned by you instead of me. I would delete my post immediately if you don’t agree with me re-posting it, but if you do, I would be really glad. 🙂
    Here is my post : http://sunny861011.pixnet.net/blog/post/63266968
    I apologise that I used your pictures before I got your permission. However as I said, I will delete the whole post if you don’t want me to translate and re-post it.
    Thank you and I really like your blog! 🙂

    Reply
    • Ashlea Wheeler

      Hi Sunny, I’m glad you liked my post! That’s fine to repost along with the links and credit to my blog – I’m glad my posts are able to reach the Mandarin community 🙂

      Reply
    • Ashlea Wheeler

      That’s great, Aimee! I’m so glad you’re heading to Boston, I’m sure you will love it! Feel free to share your tips here after your trip 🙂

      Reply
  7. Billy

    As a native Bostonian, I’m not sure why you call Beacon Hill a suburb. But otherwise, you did a great job with your list.

    Reply
  8. Anna

    This is the best travel guide to Boston I’ve seen so far. My trip is in less than a week and I was still lost XD But now I’m so excited! Thank you!

    Reply
    • Billy

      Don’t miss the Mapparium at the Cristian Science Center. It’s the best attraction in Boston nobody knows about. It’s unique in the world. You walk through a stained glass globe with the borders of the nations of the world frozen in time as they were in the early 20th century. I’m a native Bostonian. Take my word on it.

      Reply
  9. Bonnie

    Great piece, been to Boston many times and all your recommendations are spot on. I would add a tour of Fenway Park to the list. Even though folks may not be Red Sox fans, the place is a historical site well worth the trip.

    Reply
  10. Gina Elia

    You forgot in my opinion the absolute must see in Boston; Fenway Park. It is over 100 yearsbokd andbhas such a nostalgic sense and the history of thisbpark cannbe viewed throughout the venue! Of course this is only open April -October (depending on the playoffs) and then theres Jerry Remys where you can eat before the game! Just my two sense from a born and raised Red Sox fan!

    Reply

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