Date Day – Portland, Maine

Day Date - Portland, Maine Portland Head Light

To honor the near end of our favorite month, and Sarah’s birthday, we decided to implement a date day last weekend!

As a reminder for those that haven’t visited us here on Write to Getaway before, the terms to date days are as follows:

  • The date chooser changes every other time
  • The date must involve at least one fun activity and include a plan for food
  • Dates that include alcohol are highly encouraged


Since it was Sarah’s birthday, Phil took on the responsibility of planning the date. We decided together on the location: Portland, ME. A couple years ago, we made our first trip to the Portland of the east, which we captured in a previous blog post, 24 Hours in Portland, Maine. Since this first trip, we were trying to find the perfect excuse to go back to this magical city by the sea. A birthday weekend seemed like an excellent reason.

Day Date - Portland, Maine Portland Head Light

Knowing Saturday was going to be the warmer of the two weekend days we knew we had to capitalize on this fall heat with our day trip. When we awoke Saturday morning it was a mere 40 degrees outside, but the weather forecast promised temperatures in the 60s. Layers, appropriate booties, and a light jacket were a must so we could adapt to the day in front of us! We were sure to leave the house as close to 7:30am as possible, to try and miss the fall leaf peeping traffic and the tourist chaos — it takes almost 2 hours from Boston to get to Portland.

Our first stop was the quaint, but extremely popular donut shop called The Holy Donut. This Old Port bakery is known for its creative combinations of flavors and tasty gluten free donuts made with potato flour. After grabbing a glazed, apple, and maple bacon donut and delicious pumpkin coffee, we headed out to Cape Elizabeth’s Portland Head Light. This idyllic New England lighthouse is the oldest in all of Maine and serves as the entry point into Portland Harbor. Though it is open year round, we have always wanted to go in the the golden glow of fall.

At around 11:30 we headed back to Old Port for lunch at our favorite restaurant in all of Portland. When we say that its poutine is the best we’ve ever had, we mean it, and we’ve been to Montreal! Duckfat is known for its french fries fried in duck fat. So imagine a poutine with these fries as a base, topped with duck gravy, and oh yeah, duck confit. I mean come on, how is your mouth not watering?


After finishing up here, we made our way to the shops in Downtown. This strip of unique locally-owned shops makes for an afternoon of amazing window shopping. Our favorites include shops on Commercial Street, like Asia West and Motifs, and Exchange Street, like Earthbound Trading Co.

Once we finished shopping we made our way back towards Old Port, which also conveniently happened to be near the Shipyard brewery. This Portland based brewery is known for its seasonal classics like Pumpkinhead and Smashed Pumpkin. Their tasting room is one of our favorite spots; groups of friends and tourists alike collect to play board games and taste the newest concoctions and classic favorites. We each got a flight and enjoyed a little alcoholic treat before heading home.

Not long after we finished our drinks, we hopped in our car and made our way back towards Boston, munching on our leftover maple bacon donut along the way. We can’t wait to head back here in the near future!

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