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  • Writer's pictureKassie

Southern Maine and Boston, Massachusetts

Southern Maine and Boston are beautiful. There are so many quaint streets and homes that made me feel like I time-traveled back to the revolutionary war. I am somewhat of a history nerd, so I love trips like this that have seemingly endless opportunities to experience history in new ways. Besides visiting New York City and Washington D.C., this was my first trip on the East Coast where I felt like I got a good feel for what it's really like to live there. Maine reminded me so much of Northern Minnesota, I felt so at home! And Boston was full of fun things to do and see. My planner-mind went a little crazy on this trip since all we had planned were the hotels we were staying in and the car we were driving. But, it all worked out and we stumbled upon some amazing new places (including a bunch of healthy restaurants I was pleasantly surprised by!). I would love to go back and spend even more time in these areas in the future! So, here are some of the places I recommend going to if you are hoping to visit this area of the U.S.

Kennebunkport/Kennebunk, Maine

We started out our trip in Kennebunkport, Maine at a bed and breakfast. This ended up being our favorite place of the entire trip. Kennebunkport is a charming and welcoming fishing town (possibly the most picturesque town I have ever seen!) with perfectly manicured lawns and homes. It is right on the coast, with big rocks jutting out into the water and waves crashing in. President Bush Sr.’s family has a summer home here. I highly recommend driving along the coast in this area because it is stunning. There are several homey bed and breakfasts and small hotels in the area. We stayed at the 1802 House (link below), which had the sweetest host and cleanest rooms. The host lived in England for awhile, and the house definitely reflected it! It was walking distance from the downtown area and several restaurants.

I was expecting it to be difficult to find gluten free food in this area, but to my surprise, it wasn’t! There were several restaurants we could have eaten at, with a lot of lobster and fresh vegetable options. Our host at the 1802 house even made us gluten free breakfast each morning. For lunch we ate at a restaurant she recommended called “Mabels,” which is in downtown Kennebunkport. Jacob and I split a lobster there and then ate at Federal Jack’s Restaurant and Bar for dinner. This restaurant had a fun atmosphere with a ton of indoor/outdoor seating. The food was great; I had a quinoa salad, Jacob had haddock, and of course we shared what we can never resist: sweet potato fries. The next morning we went to Moon Rose Cafe that had GF scones, coffee, kombucha, sandwiches, and superfood smoothies. I would have eaten at this coffee shop every morning if we would have stayed in Kennebunkport longer!

For lunch, we got GF paninis at New Morning Natural Foods, a natural grocery store in Kennebunk (same just without the “port”). This place was the perfect little grocery store with an impressive array of stock. The staff was so friendly and the café could adjust meals to avoid a wide variety of allergens. We went here for lunch twice because of how accommodating their café was for allergies! Downtown Kennebunk was also fun to walk through and I highly recommend driving around this little town to look at the old homes dating back to the 1700’s. It is just a short drive away from Kennebunkport where we stayed.

Another tip on the Kennebunkport/Kennebunk area: the locals told us we came on a great weekend because if we would have come a week later, it would have been the beginning of their busy season. Apparently it can get so crowded there that the restaurants have 2 hour-long waits! So if you want to visit this area in the spring, try to go before the last week of May!

Portland, Maine

This city was very similar to Duluth, MN. Artsy, beautiful, and little quirky. This town is great for shopping local goods and walking around all day. The downtown area has a lot to do, with a fun atmosphere. We stayed at the Marriot Courtyard, which was great because it was walking distance from the waterfront and downtown. I highly recommend visiting this area because of the Portland Head Lighthouse on Cape Elizabeth. This was by far our favorite part. The lighthouse is the most photographed lighthouse in the nation, and understandably so – it is gorgeous! It is just a short drive away from downtown Portland.

We ate dinner at a vegetarian Thai restaurant (on accident – Jacob missed having meat lol) called the Green Elephant. The food was very fresh and flavorful, but pricey considering there were no meat products sold. After dinner we got gelato at Gorgeous Gelato, whose owners used to live in Italy, and having visited Italy ourselves, we agreed it tasted authentic. The next day we ate brunch at Local Sprouts Coop (good food, not the best atmosphere) and got coffee at Bard Coffee which had “decent” coffee (according to my coffee connoisseur husband). After walking around downtown for a while, we sat outside on a pier where Jacob had some great lobster at the Portland Lobster Company. I got a smoothie at Maine Squeeze which had a wide variety of options for milks, fruits, and proteins.


We stayed just outside of Boston in Medford, which I do not recommend. The hotel we stayed at was overpriced (we did visit Boston during Harvard’s graduation week though…), and the town of Medford was nothing special. We drove into Boston, but driving in Boston is not necessary because the city is so walkable! We wished we would have taken the bus or Uber-ed there. We walked the entire Freedom Trail that day with our friends without using our rental car at all. We found parking in the Ritz Carlton parking garage for about $30 for the entire day, which was one of the cheapest options we could find. The Freedom Trail was really interesting, but we wished we would have downloaded an audio tour or went on a real tour so we could have learned even more. Nevertheless, it was fascinating to see all of the important historical sites from the Revolutionary War.

We had mediocre GF waffles at The Paramount on Beacon Hill. This area is super fun and picturesque. We wished we would have eaten at Tatte Bakery and Café instead because they had GF toast and muffins, and Stumptown coffee. They also had THE BEST matcha latte I have ever had at a coffee shop. I got it with oat milk and added honey. This café was actually in an old church and appeared to be one of the busiest coffee shops in the area. Around lunch time, we walked through the historic Quincy Market (also called Faneuil Hall), which was super fun. There were tons of food options, but not a lot of healthy ones. So, we ended up eating lunch at our best find yet: the Boston Public Market. This indoor marketplace was modern, clean, and full of different options. There was a noodle bar, fresh apple cider (the hibiscus apple cider was amazing), a smoothie/juice/salad place called Mother Juice (where I got my lunch), and Inna’s Jewish Cuisine that Jacob ate at (shawarma, falafel, etc.), a donut stand, coffee shop, and even an allergen free baked goods stand called Jennifer Lee’s Gourmet Bakery (there were GF Donuts). After walking the rest of the Freedom Trail and parting with our sweet Canadian friends, we went to the Italian District (in the North End) to La Familia Giorgio’s. This restaurant made us feel like we were in Italy all over again. The staff was so friendly and spoke Italian to each other. And the best part: they had three different freshly made types of GF pasta. We both ate pesto pasta and it was the best GF pasta either of us had ever had.

The second day we were in Boston, we ate at another Tatte Bakery and Café right next to Harvard University’s campus and walked around there for a while. Then we drove to Lexington and Concord, which was also a favorite of this trip. Lexington was somewhat hard to picture, as the battle happened on a small open area in the middle of town. But the area around Concord seemed to be preserved well, a lot of the old country homes that would have been there during the battle were still standing, and the bridge where the battle began was kept up as well. This was easier to imagine, and it gave us a new awe of the freedom we have in the U.S. today. We went back to the Boston Public Market for lunch and then headed to the airport!


Marriot Courtyard

Portland Head Lighthouse on Cape Elizabeth

Quincy Market

Boston Public Market


Mabels Lobster Claw Restaurant

Federal Jack’s Restaurant and Bar

New Morning Natural Foods

Gorgeous Gelato

The Portland Lobster Company

Tatte Bakery and Café

Boston Public Market

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