Daytrip Around Portland & Peaks Island

Summer in the city can get quite sweltery, so we curated a Daytrip around our sweet city and wove in as many opportunities to catch an ocean breeze as possible.

Still in bed, we placed an online order for Tandem Coffee and then quickly made sure our bikes were tuned up for the day before rolling down the street. We are spoiled to have this great coffee shop in our neighborhood. We got some breakfast sandwiches, a sticky bun to share, and iced coffees. If you haven’t tried their malt iced coffee, it’s a summertime treat!

By bike, we cruised through the city, dropping down from the West End and along Commercial St. to the ferry terminal where we got round trip tickets for us and our bikes to Peaks Island. We enjoyed our breakfast on the ferry over, counting lighthouses and pointing out the Casco Bay islands as we went. About fifteen minutes later, we arrived on shore, cruised up the hill, and opted for a left at the intersection to bike clockwise around the island. Just after the turn is Brad’s Rental & Repair bike shop, perfect if bringing your own bike isn’t convenient for you. While we personally think bikes are the ideal way to see Peak's Island, there are also golf cart options available for rental and tours if biking isn't feasible.

Island Ave took us past charming homes, artist studios, and eventually to Evergreen Landing, where we soaked up the scenes of Casco Bay. We retraced our steps a bit before finding Seashore Ave, with breathtaking views of the big blue. The swells coming off the ocean made a beautiful noise when we paused for a snack at Whaleback Ledge before walking our bikes into Battery Steele, a WWII fort that is completely overgrown on top and artfully graffitied inside.

By this time, we were ready for some lunch, so we cruised down to the Lion’s Club, where a new wood-fired pizza place just joined the island’s food scene. Il Leone was started by Ben Wexler-Waite and was inspired by the simplicity of Neapolitan-style pizza. The emphasis is on quality ingredients, sourced locally and from Italy, which comes through in every bite. They also have some Gelato Fiasco available for those hot summer days. This pizza alone is worth a trip to Peaks Island.

While we waited for the 3:45 ferry, we popped down to Picnic Point and bathed on the warm rocks. Even if just for a day, the pace of island life is such a dream to slip into. When it was time, we wandered back to the ferry and hopped aboard to Portland.

We dropped our bikes off at home, then walked down to Hadlock Field to catch our first Sea Dogs game of the season. Our seats were in the bleachers behind home plate, positioned nicely to call balls and strikes ourselves. We enjoyed a sausage with peppers and onions and of course a Sea Dogs Biscuit, savoring the nostalgia that is baseball in the summertime. The game was eventful, with two home runs that set off the lighthouse in the outfield and ended the night with fireworks celebrating the win!

We love living in Portland and it’s days like this that remind us why. With so many things to do throughout the city and the surrounding islands, we hope this inspires you to enjoy Portland too.

If you've been enjoying our Daytrip series, we would appreciate your support of our publication. We’re releasing Issue 09: South this week, which is filled with the same high-quality storytelling, compelling visuals, and much more that comes with holding a timeless publication. Visit Portland!

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