• Menu
  • Menu
12 essential activities for a weekend in Boston

12 essential activities for a weekend in Boston

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. Here are my 12 essential activities for a weekend in Boston!


HI Boston Hostel

Where we stayed:

Rob and I based ourselves 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-conscious 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.


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 this guide and walked along Chestnut Street and Acorn Street.

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 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. If you want to do the trail independently you can follow this map, or you can jump on a Freedom Trail walking tour to learn about the history of each stop in more depth.

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 – it was ok, but I’m sure there are better places to try a slice of pie!

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

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 off the Harvard website but to be honest it was rather difficult to follow! Alternatively, you can 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. Do this area on your own, or do a North End secret food tour.

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.

Candlepin Bowling at 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!

Leave a reply

Your email address will not be published. Required fields are marked *

30 comments