Celebrating 60 in Portland, Maine

Sailboat in Portland, Maine

It’s official, there is no better way to celebrate 60 years of life than an adventure in Portland, Maine!Sailboat in Portland, Maine

In the fall of 2016, my beautiful mother turned 60 (rumor has it, 60 is the new 30), and to celebrate we took an incredible trip to Portland, Maine. With an offer to go anywhere, ANYWHERE, she knew it had to be Maine.

Below you’ll be able to snag a glimpse of our week-long journey — from the restaurants where we indulged to the views we discovered — we hope it might inspire you to pay a visit too. To over simplify it, it’s worth it.

Before I jump in, I must first brag. I know we all believe we have the world’s best mom. If your mom, like mine, is your hero, then she likely is the best and deserves the best. If I could relive this week, I’d do so without question. Instead, there will be new adventures to take and memories to make, all with my favorite woman. Mom, everything I am, you helped me to be. Adventures like this could never be enough to repay you, but dang they sure will be fun. So, let’s get planning! Love you always.

Duckfat was our first stop after arriving in Portland. A small sandwich shop in downtown Portland, Duckfat offers Belgian style fries (made from Maine potatoes and fried in duck fat), paninis, milkshakes, and more! Thanks to their extensive beer selection, mom was able to have her first pint of local beer. We may have waited over an hour for a seat, but it was worth every bite. Seating is limited, with a small section outside, but don’t let it deter you. I only left with one regret: we were too full for milkshakes.

Above: Allagash Saison | Below: Poutine & Belgian Fries


A post-lunch walk around downtown and near the waterfront was needed. While we did utilize ride share services to a couple of locations on the outskirts of town, the downtown area is completely walkable. Our first day was touch on the gloomy side, but still beautiful.

We had to pop into the Harbor Fish Market to check out what locals are lucky enough to take home for dinner! Coming from a landlocked state, you could say we were a tad jealous. The exploration continued…There are few things in this world that I love more than her laugher.When at the “Bait Shack”…

I could never get enough of these cobble streets. So many times we pack our trips full of plan after plan, but it can be just as fun to explore the area without structure or direction.A full day of travel left us quite exhausted, so we headed back to our home for the week. The Hampton Inn Downtown Waterfront was perfectly located near shops, eats, and, of course, the waterfront. I’d highly recommend it for a future visit, though an Airbnb would be an excellent alternative.

Our second morning took us to the highly praised Bayside American Cafe (formerly Bintliff’s).Another hour-plus wait that luckily came with self-serve coffee. Easily one of our favorite eateries of the trip, the cafe menu boasts a large selection of breakfast favorites with a bit of Maine flair. Our morning picks were a balance of savory and sweet. If possible, I’d recommend splitting a number of dishes, as it’s quite daunting to choose between the crab cake Benedict or the cinnamon roll pancake (both pictured below). I can, however, encourage a Honeymoon drink or two.

Above: Honeymoon (mead + champagne)

You can imagine after that incredible brunch we needed to get out and about, so we headed to Portland Head Light and Fort Williams Park. Portland Head Light is a historic lighthouse located just outside of Portland in Cape Elizabeth, Maine. It is quite the tourist hot spot, but luckily our visit fell near the end of the busy season and again on a bit of an overcast day.

Just casually blending in…

We were still recovering from brunch, so gelato wasn’t in the cards. However, should you find yourself exploring the headlight, make plans to stop by this adorable little stand for a mid-hike treat.

Oh, and when you find the perfect spot for a quick portrait, take it. Cheers to the birthday beauty!After returning to downtown, we took note of our evening food spot and planned to return later after a little post-hike rest and recovery.Portland Lobster Co., a seasonal waterside lobster shack, serves up a number of New England seafood classics. It can be faulted for introducing mom to her beloved blueberry beer and raved for a spirited atmosphere that pairs perfectly with its seaside selections. Worth trying? Well, it was so delicious, we found ourselves back for a second visit.

Above: Sea Dog Blueberry Wheat Ale (aka mom’s new love)

Both visits included performances by local bands, making it a perfect way to close a night by the water.On day three, we set off to Peaks Island. While we did indeed travel by boat (or ferry), it wasn’t on the beauty below. You can check out our floating machine, if you scroll a bit further into the trip. Accessed via the Casco Bay Lines, Peaks Island, once known as the Coney Island of Maine, is home to artists, retirees, and devoted commuters. The island has a small town feel with incredible ocean views. The island is the perfect opportunity to see another side of Portland, and the roundtrip ferry ticket will cost you less than $10 per person.

We loved every second of our visit — someone was even brave enough to give us a golf cart for our island exploration. Should you plan to go, I’d strongly advise checking island store hours ahead of time. Given that we were at the end of the tourist season, several shops were closed or open very reduced hours. It didn’t impact our visit, but I’d hate for it to leave you without options.

Views from the ferry…

Arriving to Peaks Island…At this point in the trip, a kind, naive local loaned us a golf cart (for about $25). It was a remarkable way to take in all the views the island had to offer. Non-motorized wheels are available for rental too, or your feetsies will do! If you dare, click play below.


Seriously, could the island be any more perfect?

After a full day of adventures, we returned to take the ferry back to Portland. We arrived downtown hungry and ready for a fun evening. Fun it was, probably too much, so we will just keep the details behind these locks of love.  

We spent the first half of our fourth day in Freeport, Maine, home to the L.L.Bean flagship store. By this time we had snagged our rental car, as we needed it to head north for day five. The flagship store was almost like a little village of stores separated by theme. We didn’t spend an overwhelming amount of time here, but we did enjoy walking the streets of Freeport, while popping in and out of stores. Should your visit to Maine bring you to Freeport, make plans to stop by Wilbur’s of Maine. There sweet selections won’t disappoint! 

The last half of day four was reserved for a brewery tour at Shipyard Brewing Co. (or as mom mistakenly calls it, Shipwreck). The tour was fascinating, the beer tasty, but the company was best of all.

For those of you that know my mom, you undoubtedly know she knows no stranger. A young gentleman from the UK had joined the tour alone, as he was closing out his 6-month hike of the Appalachian Trail. We shared beers and stories, which led to an extended invitation to dinner. When in Maine, right?

With a new friend joining us, we headed to Taco Escobarr for evening eats and drinks. The restaurant boasts a vibrant environment with a menu to match. Swing by to spice up your trip with a puffy taco and strawberry jalapeño margarita. If you can time it right, rumor has it they have a knock out happy hour.

Day five belonged to Acadia National Park. A three hour road trip north led us to an adventure that spoiled us with unparalleled views. One could, and many do, spend an entire week in exploring the park and the quaint town of Bar Harbor. We filled a single day with stunning landscapes and local treats. If we’re being honest, the homemade whoopie pies gave these magnificent sites and run for it.

Collecting the views had us ready for lunch, which we found at Street Side Cafe in downtown Bar Harbor. The service was possibly the friendliest we had encountered (though we’d yet to have a bad one). The food was fresh, quick, and HUGE. Unless you hiked half the park, you might consider sharing. Reviews indicate this is a nice spot for a happy hour, so throw it in the mix for a post-hike pick-me-up.

Above: Mac & Cheese w/ Chicken | Below: Lobster Cobb Salad

Remember those whoopie pies I mentioned? The Pink Pastry Shop had everyone drooling. The adorable bakery offers an array of sweet treats, but there is a reason they put these beauties on display. It tends to be a life rule for me, but this time for sure, leave room for dessert!

We returned to the park, whoopie pies in hand, for some oceanside views. We begged to stay forever, but alas, sunset was upon us.

A late night return to Portland, left us exhausted with a need for fuel. So, we checked out Slab, a modern pizzeria serving up a number of Sicilian street foods. We ordered an assortment of offerings to nibble on. A single “slab” is more than enough for one, but it seemed necessary to try a few items. It was a pretty slow night, but the waitress was incredible and offered up a few tips for our remaining day in Maine.

Stiggs (sesame poppyseed breadsticks, fig red pepper sauce, saffron black pepper ricotta)

This brings us to our sixth day in Portland, Maine. What better way to start than with donuts?? The Holy Donut is a local favorite, offering nearly 20 different flavored donuts made with all-natural ingredients (including Maine potatoes). We asked the gal at the counter to assemble a 6-pack with her a combo of most popular picks and her favorites. They didn’t disappoint!

Before we found a spot in the nearby park to sample our morning sweets, we swung into Bard Coffee for a refreshing beverage. Given the number of people enjoying the Bard, I’ll assume the beverage menu is solid. I can, however, confirm their cold brew is stellar.

Admittedly, we couldn’t finish all six, but a bite or two of each was a must. We spent the day wondering the streets of downtown, stopping in local shops to snag trinkets and tastes of Maine to take home.

Lunch was held at a small diner. Well known in Portland and full of locals, Becky’s Diner has called the waterfront home for more than 25 years. I couldn’t resist another lobster roll, and mom enjoyed what she claims to be the best tuna sandwich she’s had to date.

Becky’s is always bustling, so take the seat you can get. But, should the opportunity present itself, pull up a seat at the diner’s counter, chat with a local, and request the bottomless coffee.The afternoon and evening included a two-hour windjammer sail on Casco Bay with the Portland Schooner Company.

We boarded the Wendameen and set out to experience the beauty of the Maine coast, complete with lighthouses, sailboats, seabirds, and the rugged coastline.The company encourages you to pack a meal and bring your favorite wine or beer to enjoy as the crew shares their knowledge of the sea, sailing, and local history.

The experience was unforgettable. We sipped our favorite local beverages (you know mom had her blueberry beer) and mingled with visitors and members of the crew, all while taking in the cool-breeze of the sea and stunning sunset. The Wendameen has a capacity of 49, but, once again, we enjoyed the perks of being outside peak tourist season. At most we had 15 on board, including the crew! Just another reason to consider the timing of your visit. We closed out that night with a cold treat from Gelato Fiasco. They note the gelato is inspired by Italy and perfected in Maine, and you can find it in your grocery store freezer—and you should!

We caught a street performance and turned in for the night to rest up for our final full day.

Sadly, we were met with our final day in Portland, Maine. We enjoyed a mead tasting at Maine Mead Works, which was tasty but not a brag worthy experience. I’d encourage you to try mead, and the tasting may just be the most cost-effective way. Unfortuantely, this particular tasting experience was far from memorable. Upon leaving our mead tasting, we spotted an incredible cemetery and spent at least an hour exploring the stories of those before us. Weird? Yes. Creepy? Sure. Awesome? Duh. While it didn’t work out for us, we learned there are organized tours. So, if you’re interested in these sorts of outings, it’d be worth checking out.El Rayo Taqueria brought us our last lunch, and boy was it worth the weeklong wait! The tacos and guacamole were dynamite, but I’m still dreaming about the spicy margarita. It’s the perfect spot for a quick bite, or find a spot on the patio and soak up those rays all afternoon. We spent our remaining afternoon walking a trail along the waterfront. As we watched sailboats coast in and out, we fondly reminisced about the week behind us and refused to accept it was drawing to an end.

It was only fitting that we sealed the trip with a return to our favorite seaside lobster shack (Portland Lobster Co.), before turning in early to prep for our wee-morning flight. A small collection of iPhone images (mostly selfies)… 

It’s impossible to put into the right words just how much this trip meant to me. Maine will always hold a piece of my traveling heart, and even more so because of who I was with when I visited. Mom, you deserve the world. I can only hope to show you it one adventure at a time.

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