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  • Writer's pictureSarah Jayne

Family Fun in Portland, Maine

We enjoyed a long weekend in Maine this year, and I’m here to share my top recommendations for a 3-day family trip to its beautiful harbor city, Portland. ⛵️


Day 1


🛎️ First we checked into our family-friendly accommodations at The Docent’s Collection located right in the heart of Portland’s Old Port.


🚃 Then we took a trolley tour and visited Portland Headlight Lighthouse, a historic lighthouse located just a few minutes drive outside of Portland. This picturesque lighthouse was built in 1791 and is Maine’s oldest lighthouse.


🦞We ended our first day with a delicious lobster dinner at Highroller Lobster Co. (*Note: their lobster rolls are divine, and my girls loved the lobster corn dogs - yes you heard me right - lobster covered with cornbread. Just trust me on this one.)


Day 2


🎭 Our second day was spent at the the Children’s Museum & Theatre of Maine. We’ve been to a lot of Children’s Museums, and let me tell you, this one was a definite favorite. The Children’s Museum & Theatre of main offers three floors filled with state-of-the art exhibits, along with a full outdoor playground and garden to enjoy. Maddy’s Theatre is located inside, and we took the girls for their first theater experience to see “Charlotte’s Web”, which they loved.


🍕 Lunch stop recommendation: Flatbread Company Portland. We all LOVED their pizza, including my youngest, who is dairy free and had their vegan option.


⛵️We spent the afternoon exploring the beautiful Portland harbor, and having a full lobster dinner at Luke’s Lobster with a gorgeous view of the water.


Day 3


⚓️We spent our third day exploring Portland’s Old Port. It is beaming with rich history and culture with countless local small shops to discover. We enjoyed walking around and taking in the architecture, listening to some live music, and stuffing our faces with potato donuts from @holydonutmaine .


For more info on everything we saw and did in Portland, check my latest story highlight on @thismessymamahood and follow along for more family travel inspo. ✨




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