Portland, Maine

With the official beginning of summer upon us, we decided to celebrate with a proper New England weekend trip to another state needing to be checked off the list (by Garret), Maine. Emily had been wanting to go back and not only see some of the places her family had visited before but also explore some new parts of the state. It turned out to be a great and easy trip, where we enjoyed the relaxing nature of Portland and appreciated the plethora of lighthouses and lobster. Yes, Maine requires some additional travel time for a trip in the Northeast, but it is well worth the trip and after this one we definitely want to come back and explore the rest of the state.

Friday May 22nd

We took full advantage of the first work “summer Friday” of the year (for one of us!) and headed out of the city in the early afternoon, grabbing a rental car at Newark Penn Station (see our opinions on renting a car here). The drive from New York up to Portland could be considered long for the New England area but not bad at all for us Midwesterners; five to six hours, and traffic dissipated once out of New York tristate area.

By the time we arrived in Portland that night the only thing on our minds was consuming Maine lobster.  We decided on the Portland Lobster Company, right along the water.  It turned out overpriced but the food was good and the employees very friendly, as we arrived right before closing. The band was just packing up, but we imagined how an evening spent outside on their patio/dock with a signature lobster roll and local blueberry beer complimented by live music would be a fun time.

Tasty first stop in Portland!
Tasty first stop in Portland!


The initial motivator for our weekend in Portland was an adorable bed and breakfast Emily stumbled upon online, The Inn at ParkSpring. It was absolutely perfect for our weekend trip – great location, free parking, and inexpensive for a private bed and bath plus a gourmet breakfast served on the main floor every morning by the enjoyable staff.

Great service, great price, great find by Emily.
Great service, great price, great find.

Saturday May 23rd

Exploring Portland

After the gourmet breakfast we went to the farmers’ market in Deering Oaks Park to pick up some light picnicking supplies for later on – bread, cheese and jam, all fresh and local. Our appetite started to pick back up as we headed to downtown Portland, a fun place to window shop. While walking around we encountered a line protruding out of The Holy Donut, and after a short wait in that line proceeded to take care of our hunger with a couple hearty potato-based donuts, including a very tasty blueberry donut.

Donut miss these when you visit Portland.
Donut miss these when you visit Portland.

In the afternoon we checked out Maine Mead Works.  This local honey/mead establishment was a mix between a winery and brewery.  The staff was very friendly and took us on an impromptu tour of the facilities.  It was very interesting and educational to learn the history and production of mead wine.  A fun afternoon stop if you have some free time and enjoy wine.


After the urban winery we went searching for the numerous lighthouses in the area. Our favorite was the Portland Head Light, a still-active lighthouse commissioned by George Washington in 1787 and the oldest of the 60+ lighthouses in Maine. It sits within Fort Williams Park, which the military used in both WWI and WWII to protect Portland.

Lighting the way for the ports and forts of Portland
Lighting the way for the ports and forts of Portland
Portland Head Light
Garret decided to hop a fence and climb the rocks to get a different perspective/picture of the Portland Head Light.
No lighthouse too small.
No lighthouse too small.

While in Maine one must, of course, indulge in as much lobster consumption as possible.  We did some quick research online and decided to indulge in a lobster dinner at Street & Co.  We were only able to get a late reservation, but showed up a bit early and had a glass of wine in their fun casual lounge before our table was ready.  The restaurant had a great vibe, with an open kitchen that allowed the tables to witness lobster dish after lobster dish being prepared and sent out, leaving the guests to ponder which lobster would finally head to their table.  Our bellies full of lobster and wine, we were still able to walk back to the B&B at the end of the night.

Sunday May 24th

Peaks Island

On our second day we decided to venture to Peaks Island.  After a quick breakfast at the B&B we walked to the ferry landing downtown, arriving close to the ferry departure time. There was a general rush to both buy tickets and get onboard, so we recommend 10-15 minutes for the ticket purchasing process as the line can be pretty long during a peak time and popular summer day. It was fun being on the top level of the ferry and taking in the harbor, which is full of smaller islands, old forts, and new houses with some great views.

Fort Gorges, similar design to Fort Sumter, constructed in the middle of Casco Bay.
Fort Gorges, similar design to Fort Sumter, constructed in the middle of Casco Bay.

Once on the island we rented bikes for the day.  One thing to note, there are golf carts for rent as well, however the perimeter of the island is easily bike-able and biking seemed far more adventurous and liberating.  The island itself is beautiful and has equally beautiful houses.  The east side of the island has several areas where the shore is comprised of large boulders, providing a good spot for sun bathing.  On the northern side of the island there was a small park area with some picnic tables next to the main sandy beach.  We chose this area to enjoy our purchases at the farmers market the day before.

Peak's Island
The simple pleasures of life – bikes, food, and a relaxing island.

Monday May 25th


On Monday we started the drive back to NYC but not before stopping at Kennebunkport to walk along the main street and check out an old stone church Garret’s parents recommended. We ended up also checking out the Bush compound.  As we stopped at a lookout point to take some pictures Emily spotted Barbara Bush, and we played paparazzi by snapping a photo.  On our way out we explored one of the numerous antique shops they have, with endless lobster traps and classic buoys. Overall Kennebunkport was a quintessential Northeast town that made for a fun end to the trip.

Barbara returning from the Memorial Day parade in Kennebunkport
Barbara returning from the Memorial Day parade in Kennebunkport.

(De)parting words of advice!

  • Driving, versus the usual train ride, in New England can be a refreshing change of pace.
  • Portland is a great place to explore over a weekend, and being in the southern part of the state easier to access.
  • It doesn’t get any fresher than lobster in Maine, it’s the OG.

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