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Beginning in the heart of Portland’s Historic Old Port, we will first head down to the working waterfront and the acclaimed The Holy Donut, skipping the likely line out the door, to indulge along the storied Long Wharf.

Meandering back along the iconic cobblestone streets of our donut trail, we’ll make way to the granite built Customs House, imagining a thriving 1800s port of tall ships unloading goods. Onward, past the armory, now a historic gem of a hotel, in search of Captain Mowatt’s remnant canon balls that originally burned down the city via harbor canon fire in 1775.

Just up around the corner, is our second stop, Eighty 8 Donuts, once a food truck busting at the welds, now Portland’s newest fried dough all-stars are known for their delectable bite-sized treats all over the state. There’s no better place to appreciate these culinary delights than right along the granite of City Hall! Just beware, this building has burned down three times, along with much of the rest of the city. Continuing on to take in more of the rich history of the Downtown peninsula – our oldest church building, a congregation dating back to 1674, and the picturesque Monument Square at City Center.

Then, our final donut stop of the tour- HiFi Donuts, staying true to old world styling while glamorous in new world foodie goodness. By this point, you should be dumbfounded by just how all three of these world class bakeries are within our short storied walk of one another, and agree – this is the sweetest walk there ever was! Only a short jaunt remaining from here, but much to take in of our lobstering history and charming architecture. We couldn’t be more excited to celebrate these donut shops and our city with you. See you soon!

Located at The Maine Souvenir Shop, 2 Exchange St, Portland, ME 04101