It’s not hard to have an ideal day while living in Boston. Between the outdoor spaces, museums and cultural spaces, food scene, and numerous ways to move through the city, you’re more likely to have too many options to choose from than you are to not find anything to do! But, with so much to do, it can be a challenge to figure out how exactly to spend your ideal day. To help out with the decision paralysis, and to give you another route to try, I’ll share here one of my preferred routes for an ideal Boston day.

Brighton Common to Harvard Square

I’ll be starting from Brighton Common, which is around the corner from my house. I’ll be biking north today into Harvard Square via the Dr. Paul Dudley White Bike Path, but you could also take a bus for this leg.

Harvard Square

Harvard Square is an exciting and lively part of the city, and we’re actually in Cambridge now as well. There are tons of shops and restaurants to explore here.

From Harvard Square, we’ll ride the Red Line to Park Street Station at the Boston Common. This portion of the Red Line has one of the best views in all of Boston and bikes are allowed on the Red Line. 

Boston Common and Boston Public Garden

Boston Common was the first public park in the U.S., and remains a beautiful area to stroll, hangout, and, as I will be doing, eating! Our first goal here is to find my preferred hot dog stand, which today was located at the westernmost point of the park before crossing the street into the Public Gardens. 

Having secured a hot dog, we’ll cross into the Boston Public Garden to find a great spot to eat. The Common and Garden are technically two different locations, but the experience and spaces share a beauty and are both excellent places to explore. 

Castle Island

Next, I’ll be riding from the Garden to Castle Island in South Boston (you can also catch a bus at the corner of the Garden!).

I love this part of the city—there are opportunities to stroll, swim, eat, and just generally relax. You also must try Sullivan’s for all your classic beach food. Since I already ate in the Garden/Common, I’ll just be having a milkshake today!

Castle Island to BC

It’s time to head to my last activity today: frisbee with an CSTM friend at BC! To get there, I’ll be riding my bike to campus, which will be the longest riding leg of the day.

This was a perfect night to see campus as the day’s heat fell away and the sunset’s colors were incredible!

And home again

After frisbee I rode home in the dimming light, and settled into a calm evening. If you’re looking for a nearly-bursting schedule for an ideal Boston day, then this might be just what you’re looking for!

When exploring a city as wonderful as Boston, what matters is getting out there and seeing what you can find, so I hope this gives you at least a start to your own list of ideal Boston days! Thanks for following along through my day, now go take on Boston’s many beautiful spaces and places!