3 minute read

Portland is a straight shot from Boston located just within the two hour drive radius. It features a rich food scene and feels like the Duluth, Minnesota of Boston. After a visiting scholar said that Portland was the top destination on their to-do list for New England, I decided to head down in late July.

Portland Head Light

The first destination on our travel list was the famous Portland Head Light. Leaving Boston at 8 AM, we arrived a little after 10 and the parking lot still had plenty of spots on a Saturday. There are a lot of viewpoints you can admire the lighthouse from, and we spent the morning on a combination of trail hiking and rock scrambling. There are also tons of rose bushes around, so I imagine that earlier in the summer the lighthouse looks beautiful with the foreground of blooming roses.

Portland Head Light
Is it just me or does the lighthouse look like the one on Cape Cod chips?

After exploring the trails around the lighthouse we headed to the Bite into Maine food truck for some lobster rolls. Many places rate this as having the best lobster rolls in the country. I opted for the 36 ounce size but after comparing the amount of lobster meat with my friends’ 24 ounce orders, I couldn’t notice the difference at all… Regardless, the lobster roll was tasty, and it was really relaxing to sit along the coastline and hear the waves with lunch.

Lobster roll
Scrumptious. Get the 24-ounce one though.

Portland

Portland is where things can get a little dicey for folks like me. Portland has a rich coffee shop and bar scene, neither of which I indulge in. Instead we spent the afternoon in Portland’s Old Port wandering around and exploring the cobblestone roads and various shops, including:

  • Sherman’s: (Purportedly) Maine’s oldest bookshop.
  • Wharf Street: Old cobblestoned street.
  • Shipwreck & Cargo: Fun gift shop.
  • The Holy Donut: Potato-based donuts with great flavors. Really enjoyed these.
  • Harbor Fish Market: Great little seafood market and even better if you’re actually going to cook something from here. Apparently they offer morning tours where you can go with lobster fishermen.
  • Edgecomb Potters: Well-made pottery I can’t afford.
  • Portland Art Gallery and Greenhut Galleries: Art galleries. The second one has some really funny seagull art by Mike Stiler.
Lobster pots
Along the pier near Harbor Fish Market; you can see the lobster pots.

We then headed over to the Eastern Promenade. At the East End Beach we hunted for crabs and my co-worker found a shy one. The promenade loops back to the Old Port and is a nice walk along Casco Bay.

Old railway
Some section of old railway also travels along the Eastern Promenade.

Finding a place for dinner is a real struggle during the tourist season in Portland. We started searching a bit before 5-ish and saw lines of people outside the popular restaurants waiting for them to open. Since the area caters to Bostonians, the prices are also Boston-like. We ended up choosing Izakaya Minato; I had some pretty good okonomiyaki and a squid appetizer special that I don’t remember the name of. It definitely benefits to find a restaurant early in the summer, since we just managed to grab a seat. The folks after us were looking at 1+ hour wait times.

To wrap up the day we headed to the Bug Light Park, which features a small, short lighthouse at the mouth of the port of Portland. From here you can see the sun set over the city. Although it had been cloudy earlier in the day, the sky let the sun shine through a bit and resulted in a sunset with golden yellows followed by vibrant magentas (it was a 30-minute show!). Needless to say it was one of the most memorable sunsets I’ve ever seen.

Bug Light sunset
Fantastic sunset captured with the Expert RAW app and edited in Lightroom on my S22 Ultra.

Getting There

Getting to Portland via car is extremely easy as it lies straight off of I-95. I’d recommend getting early to the Portland Head Light since the parking lot fills quickly. Street parking in Portland itself can also be tricky, but there are lots of parking lots just a short distance from the Old Port.