For the summer of 2024, Ashley and I decided to explore some of New England since visiting NYC and Philadelphia in previous years. Having friends who’ve visited and recommended that part of the country as recently as February, we wanted to see and experience it for ourselves. Our week-long itinerary included the following:

Fly into Boston, Massachusetts
Drive to Bar Harbor, Maine
Drive to Camden, Maine
Drive to Portland, Maine
Fly home

I’ll be doing blog posts for each day of the trip, as well as what we saw in between. Since Boston was the first on the list, we’ll start there.

(NOTE: If you’re reading this through Reeder or other RSS feed software, I would recommend clicking through to the actual site as the format looks better.)

NORTH END

We dropped our bags off at the Courtyard Marriott by North Station in Little Italy, otherwise known as North End. The neighborhood is known for its Italian restaurants, bakeries, and markets, as well as festivals that revolve around Catholic saints. It’s one of the smallest residential neighborhoods, as well as the oldest, in all of Boston.

The Freedom Trail, a 2.5-mile long path that starts downtown, runs through the North End and past several prominent historical sites, such as the Paul Revere House (1680) and Old North Church (1723).

*The North End is hilly, with tight streets, very old architecture, and Italian-American personality.*

Since we got into Boston around 3 PM, we decided to beat the dinner rush and head to Regina’s, the oldest pizzeria in Boston. It was packed, so we sidled up to the bar. The pizzeria opened in 1926 and apparently still uses their original brick-oven pizza recipe. My pie (pepperoni, black olives, and anchovies) was dangerously delicious; I wanted so badly to eat it, waiting for it to cool down wasn’t an option, and I ended up burning the roof of my mouth. Worth it, though.

*A rollerblader zips past the line in front of Regina's.*

*Since we sat at the bar, I got a glimpse of how the pizza's made.*

Our appetites satisfied, we hungered for exploration next. With no path mapped out, we aimlessly wandered the streets of North End Boston. A taste of what we saw below.

Of course we couldn’t go to the North End without stopping at Mike’s Pastry. While it’s recognized as a tourist destination, we still wanted to experience Boston’s most famous cannoli. The wait looked longer than it ended up being, thankfully. The cannoli was worth it, too.

*The crowd outside Mike's Pastry is no joke. Be prepared to stand in line for delicious baked goods and sweets.*

Cannoli eaten and enjoyed, we continued walking the North End toward downtown.

*A beautiful corner just up the street from the Paul Revere House.*

DOWNTOWN + BOSTON COMMON

*Downtown Boston as seen from the edge of the North End.*

We walked through indoor and outdoor markets as we explored downtown. We saw Boston’s legendarily ugly city hall, the country’s oldest continuously operating restaurant, and much more.

*Outdoor market with loads of fruits and vegetables for sale.*

*The exterior of Union Oyster House, the country's oldest restaurant, from later that evening.*

*A truly ugly and interesting city hall. I'm very much into this monstrosity.*

*Another shot of it in better light the day we left.*

*Fanueil Hall, or as my aggressively marketed-to brain wants to call it, "FanDuel Hall."*

*Quincy Market interior. Ashley got a delicious juice while in here.*

*Old City Hall, built between 1862 and 1865.*

*The entrance to the Orpheum Theatre hopes we have a great summer.*

*A view of the Custom House Tower through a foreground of red brick low rises.*

Having walked about 10 miles at this point, we finally decided to call it a night on exploration after visiting Boston Common. Personally, I wanted to see the critically panned Embrace sculpture by Hank Willis Thomas. I’d read the complaints about it when it was unveiled, but I don’t necessarily agree that it’s as bad as everyone says it is. Do I love it? No. Do I think it’s pornographic and awful? Also no. It’s just a weird sculpture of a hug that did its job getting people talking about art. Whatever it is, it’s unforgettable.

We finished the evening with tiki drinks and headed back to the hotel for a good night’s rest. Overall, it was a good first day of vacation.

*Embrace, a sculpture by Hank Willis Thomas that attracted negative attention despite its positive subject when it was unveiled.*

Next time on the Summer Trip Series: We go to Fenway, Newbury Street, and stand on top of Boston’s highest skyscraper.