Cooking Travel

72 Hours in Portland, Maine

June 7, 2018



Maybe you want a low-key break from the Big City, or, maybe you want a little excitement away from your rural town. Either way, wherever you’re from, somehow, Portland, Maine fits the bill.


This coastal city has small-town charm, but enough choice to have you planning your next visit before you’ve even left. Here, is a quick rundown of an extra-long weekend fit for mamas, dadas, toddlers, foodies, wanderlusts, and sightseers alike. 




Maine's Eastern Promenade


Portland Happiness


We arrived into Portland, Maine, around 3:00PM. The five hour drive from NYC to Maine, is best done outside commuting hours, and over my child’s 2.5 hour afternoon nap, so leaving in the late morning definitely worked out well for us. Our 3:00PM arrival time allowed us enough time to get settled into our Airbnb, and take a lovely pre-dinner seafront walk along the Eastern Promenade, where we admired a picturesque scene of floating sailboats from a quaint gazebo. The tone was set for Maine, whose fitting, unofficial motto is “The Way Life Should Be.” Sitting along the Promenade, cares just drifted away, and nothing but my family, the sea, and good conversation seemed to matter. After this transformation, I had no problem heading to our first dinner out, in a messy bun, hoodie, and flip flops. The best part: I fit right in. 


The seaside, casual, carefree vibe around Portland does not mean the city is not sophisticated, by any means. Quite the opposite, actually. Our dinner out at Little Giant was proof that fine food and design can be found in between donut and lobster roll shops. The refined dishes served atop Scandinavian furniture were among our favorites, and we were very fortunate to find a nice place that was welcoming to children and complete with high chairs. My only criticism: the acoustics. We were among the first in the restaurant (due to my baby’s early dinner time) and it felt like every loud moment my child had wasn’t exactly blending with the crowd. (Which could also be a criticism of my own child’s attitude that evening.)  




7:00 baby bed times mean forced relaxation for parents! No more going out til the wee hours, and ruining the following day with a hangover. Though sometimes I miss those pre-baby nights, it is nice to finish up a Friday night away with some nice chats, (away from the daily work or household grind) a couple glasses of wine, a good book, and an early bedtime! 


So, feeling refreshed on Saturday, meant an early visit to the Portland Maine Farmer’s Market. The market had such a great energy of happy weekenders checking out local selections of meats, canned jams and pickled veggies, flowers, soaps, jewelry, and more, all while musicians, performers, and people offering “free hugs” hung out on the lawn. There we picked up some meats, cheeses, and dips for a low-key Sunday dinner at our Airbnb.


We had an early lunch at The Highroller Lobster Co. for an inventive take on your typical lobster roll, offering different sauces and mayos, and a few other decadent lobster creations. The lobster “diner” has a Five Guys or In-N-Out burger vibe, with vibrant red and white, retro decor. It was a perfect setting for my daughter’s first bite of lobster! 




My husband offered to stay with my daughter for her afternoon nap, which gave me a little time for some self-love and to check out the shopping in downtown Portland. There, I had a relaxing manicure and pedicure at Anna Philips Nail Bar (where the sweet staff offers friendly conversation and a glass of bubbly), and then treated myself to a much needed bra upgrade (which everyone should do for themselves after 12.5 months of breastfeeding!) at Aristelle. There, I found four, reasonably-priced, versatile new styles, that were a very positive result of my champagne buzz. Another cute boutique, Blanche & Mimi, for mediocre customer service, but adorable baby clothes and home furnishings. 


Saturday was finished off with an amazing, totally unique meal at Grace. This restaurant is actually located inside a former church, renovated to include an open kitchen, full circular bar, and two levels of dining. The experience at first felt silly, like a setting for the Take Me To Church music video, then wrong as we sipped our cocktails, then bizarrely spiritual as our cocktails hit. But jokes aside, the food was delicious and the service was stellar. The desserts, however, were the low point of the night, which is always an annoying way to end a great meal.



Grace, Portland


Inside Grace, Portland




Sunday was my kind of church, starting off at HiFi Donuts to sample their highly instagrammable guilty-pleasures, alongside a cup of joe. 


We relaxed with the findings we got to go, while the baby napped. (Yup, another nap. No more “go, go, go” vacations.) Then, we checked out another part of the area: Cape Elizabeth. This pretty little extension of the Portland metropolitan area includes Fort Wilderness Park. The park is home to the Portland Head Light, and, often, the Bite Into Maine food truck, which makes the visit a perfect place to walk around, and get your lighthouse and lobster roll fixes, in one picturesque setting. 




On your way back to Portland, you can take a quick detour, and stop off at South Portland’s Foulmouthed Brewing! This is THE most child-friendly drinking establishment I have EVER been too. Baby toys, high chairs—it was great. The staff is so friendly, and the amount of babies in there was hilarious.  


We finished up the day by cooking a nice dinner with our farmer’s market finds at our Airbnb, and just like that, our trip was coming to a close. 






Since our daughter is still on two naps, we had breakfast at the Airbnb, and started the first leg of our journey in the 9:00 hour. This allowed her to have a short nap while we drove an hour to arrive in perfect time at The Kittery Outlets. This was a nice little break to a long journey, that allowed us to go home with amazing finds for not a lot of money. FYI, I would skip the Gap outlet (the prices were not impressive at all), and focus on Banana Republic and JCrew, to name a couple! Once we finished shopping and grabbed a quick lunch, my daughter was ready to nap a couple more hours, so the ride was a breeze!


Overall, the trip was a perfect length for a manageable city. We can’t wait to go back and check out some other donut shops and restaurants on our hit list. The city is very accommodating to people with kids, and has such a welcoming no-pressure environment. As for our travel necessities, we brought our travel stroller (that I swear by), the Mamas & Papas: Acro, and our Graco Pack ‘n Play. Other than that, just the usual. Every place we visited had high chairs and kids menu options, so there were never any problems. So, if you’re looking for a place to visit this summer with young children, stop looking around and just look north!

You Might Also Like

No Comments

Leave a Reply