Portland, Maine: What American summer dreams are made of. A captivating seaside city that can be explored by foot minus the towering skyscrapers and frustrating traffic jams, an urban culture that strikes the perfect balance of chic and refinement while simultaneously being free of pretentiousness and overwhelming crowds, and as if that wasn’t enough, all the delicious damn lobster that you can possibly fit in your lobster-loving belly.
WHAT TO SEE & DO
PORTLAND HEAD LIGHTHOUSE
One of the most quintessential symbols of Maine, the Portland Head Lighthouse is a must visit on any Portland itinerary. Donning the title of Maine’s oldest lighthouse, this iconic site dates all the way back to 1791. Situated along the spectacular shores of Fort Williams Park, the landscaping throughout the expansive historical park is breathtaking, and the pleasant walking trail overlooking the craggy coast is clearly what makes this lighthouse so frequently visited and photographed. There isn’t particularly much “to-do” here–just simply enjoy the historic site’s scenic views and soak up all of its beauty and glory!
Things to know: From downtown Portland, the lighthouse is less than a twenty minute drive and there is ample free parking. Open year round from sunrise to sunset. Admission is free.
CASCO BAY ISLANDS
Board the ferry line and enjoy a few hours on the open water. Casco Bay Lines offer a pleasant and relaxing way to explore the various surrounding islands. There are plenty of seats, and as people disembark along the several stops, more seating of course becomes available. Any day spent on a boat is a good day in my book.
Things to know: Tickets can easily be purchased onsite and are also available online.
EXPLORE PORTLAND AND ALL ITS CHARM
Portland is best seen by foot, so get to steppin’. Quaint cobbled alleyways, beautiful historic brick buildings, and stylish shops enhance the city’s allure, as well as the vibrant street markets and delectable food carts (think: lobster grilled cheese goodness) that are prevalent throughout the area.
SHIPYARD BREWERY
Conveniently located on Portland’s waterfront, Shipyard Brewery is a great spot to stop in for some beer tasting fun. You can sample any four of their beers for $6.00 in their casual tasting room. The beers are great and their staff is friendly and welcoming.
Things to know: Tasting room opens at 9am Monday-Saturday, 11am on Sundays. No reservations needed.
WHERE TO EAT
Boone’s Fish House & Oyster Room
A lively restaurant that’s perfect for a quintessential Maine lunch filled with lobster rolls, oysters, and all other things representative of New England. The upstairs deck makes for a pleasant spot to sit on a warm summer day to enjoy the fresh air and waterfront views.
EVENTIDE oyster co.
This cozy restaurant is not only adorable, it’s also fantastic. As lovers of all things oysters, Eventide Oyster Co. certainly lived up to all of its hype. While their wide selection of oysters is clearly the main draw here, their lobster roll, crudo, and pretty much everything else we ordered were just as delectable. The perfect spot for lunch.
FORE STREET
This restaurant is all kinds of amazing. As soon as you walk in, you know that you’re somewhere special. The exposed brick, soapstone hearth, and assortment of wood-burning grills, turnspits, and fires all lend to a warm and intimate setting that immediately make you want to stay a while. Their phenomenal menu boasts locally sourced and seasonal fare and I swear every single thing that comes out of that kitchen is euphoria on a plate. Fore Street Restaurant has won numerous accolades and is prominently featured on the Hills’ Best Restaurants list–surely that’s just as prestigious as those James Beard Foundation awards, right?
THE HOLY DONUT
These donuts will almost make you want to go to church. Ok, fine. Bad joke. Whatever. All I know is these donuts are dangerously delicious. You’ll most likely have to wait in line for these round bites of heaven, but rest assured, time in line here is well worth it (or send your friends to wait in line while you sleep-in like we did—-thanks, Andrea and Ian!).
WHERE TO STAY
Not sure you can find a more centrally located hotel than the Portland Regency Hotel. Its prime location is within walking distance of virtually everything in Portland. The hotel’s old-world charm, spacious rooms and welcoming and attentive service all make for a fantastic stay. Definitely recommend!
DAY TRIP TO KENNEBUNKPORT
About 30 miles south of Portland lies the enchanting coastal town of Kennebunkport. The Bush family is arguably responsible for putting it on the map for us non-New Englanders, and I’m not to proud to give credit where credit is due. This lovely seaside village, dotted with adorable restaurants, quirky and cute stores, and unique art galleries, makes for a lovely summer outing.
I was so looking forward to our dinner at the prestigious and award-winning White Barn Inn Restaurant. And make no mistake, there is a lot to love at this highly acclaimed New England institution. The intimate barn setting is absolutely stunning and the service is warm and inviting. The food was good–our dinner was certainly solid, but not imaginative or innovative by any means. After eating at Fore Street, White Barn sadly paled in comparison and we all left just a little bit disappointed.
The Takeaway
This definitely won’t be our one and only visit to Portland–we hope to return again and again to this gorgeous little nugget of utopia. And besides, there are so many more lobster rolls to be eaten and donuts for others to stand in line for and give to me!
P.S. Our favorite Mainer (okay, really the only person we actually know who lives in Maine but stillll) has (thankfully) gotten over that one time we failed to mention that we’d, umm, be visiting Maine. It was a little touch and go for bit. But look! We’re friends again! Yayyyy!
Love you lots and lots, Attwood!
Next up in my American summer series: Mount Rushmore & the Badlands
Happy Traveling, All!
Recent Reads: Cooperstown, Ghent & Bruges Day Trips From Brussels, Kentucky Urban Bourbon Trail
Related Reads: Amelia Island, Charlestown, Asheville