The Perfect Long Weekend in Portland, Maine
Many people have Portland, Oregon on their bucket list, but did you know that it was actually named after Portland, Maine? Portland, Maine is known for its lighthouses, beaches and of course - the freshest lobster rolls around.
I don’t remember where my obsession and fascination with Portland, Maine came from; maybe it was the mesmerizing photographs I saw of the sun setting on Portland Head Light or Taylor Swift’s music video for Mine, but my heart was set on seeing it one day. And luckily for me, I have visited it twice now and probably once more this year as a pitstop on our way back from Acadia National Park.
There’s no shortages of sights to see or things to do in this city sitting in Casco Bay. With Old Port’s farm/ocean-to-table restaurants and waterfront features, Casco Bay Islands, delectable cuisines and breathtaking nature views, Portland, Maine leaves explorers craving more.
Explore Old Port
Known for its cobblestone streets, fishing piers, and vintage brick buildings, Old Port is a historic coastal town for all travelers. Every street is filled with boutique shops, restaurants and unique bars for the nightlife lover, including one with board games and video games. I won’t say I’m a queen in pinball, but I’m pretty darn good.
Eat Fresh Oysters at Eventide Oyster Co.
Eventide is by far my favorite restaurant in Portland. It’s worth all the hype from Yelp reviews; I dined there four times and plan on trying their new location in Boston next month - it’s that good, trust me. Their hospitality, fresh oysters, shellfish choices, and take on New England fare will make you want to come back again and again. And again. Definitely have some of their oysters with the horseradish ice and the buttery lobster roll... you can thank me later.
Try the Fries at Duckfat
After Eventide, I went across the street to have some of their famous Duckfat fries - no judging please! Their hand-cut maine potato Belgian-style fries is to die for; choose from any of their five homemade dipping sauces - the truffle ketchup and garlic mayo were the winners in my book - and enjoy.
Duckfat also serves paninis, soups, salads, charcuterie and milkshakes - all made in-house. They compost all their food scraps with We Compost It!, who offers a 30% discount for anyone who buys Duckfat’s compost from the Riverside Recycling Facility in Portland.
Ride Bikes Around Peaks Island
One of my favorite things we did in Portland was taking the ferry (a 15 minute ride) to Peaks Island, also known as the Coney Island of Maine. We rented bikes; although my riding skills were a bit rusty, I was able to manage on my pink kid bike and witnessed beautiful cottages and an unobstructed view of the Atlantic Ocean (before I almost crashed into a tree.)
Often times I sit at work and daydream about the sun reflecting on the ocean’s blues, the view from Cockeyed Gull Grill and the mint chocolate chip ice cream from Down Front. Make sure you ask for a table on the patio at Cockeyed Gull Grill, you will love soaking in the sun and watching boats coming in and out of the harbor.
Listen to Live Music at Portland Lobster Company
Portland Lobster Company is committed to serving locally source and organic seafood and ingredients whenever possible, maybe that’s why their menu is some of the best seafood you’ll ever have... that’s on top of their dockside dining experience and harbor view that allows you to see all of Maine. Nothing beats eating a delicious ocean-to-table dish outdoors while listening to live music. Make sure you check their calendar to see when and who is playing.
You can also order lobsters for delivery from Maine Lobster Now, who works with Portland Lobster Company to provide exceptional lobster meats for their customers. Maine Lobster Now handpicks Wild Caught live Maine lobsters from local fishermen.
Find a New Favorite Beer at Allagash Brewery
Allagash Brewing Company was one-man operation in a warehouse in 1995, and is now available in 17 states - talk about a glow up. Though I’m not much of a drinker, I thought a brewery tour would be fun for my partner. Allagash Brewery offers free tours and tastings (to adults 21+, of course) with a reservation seven days a week, perfect for the budget traveler and who doesn't enjoy free things to do?
Allagash strives to be an environmentally and socially responsible member of the community. A few of their sustainability initiatives include installing solar panels, LED lighting, sourcing ingredients locally and responsibly, and diverting 99.75% of all waste from landfills. They also support their local communities by giving back to local partners and teaming with Garbage 2 Garden, a local composting and waste management service.
Have the Tastiest Lobster Roll From a Food Truck
If you have just one lobster roll during your trip, make sure it’s from Bite Into Maine, a food truck with locations by Allagash Brewery, Portland Head Light and The Commissionary. Their lobster meat, along with their bread, butter and vegetables are locally sourced. Bite Into Maine supports local agriculture and aquaculture, and use Cabot Award-Winning Butter; more than 35% of the dairy farms in Maine are members of Cabot Creamery Cooperative.
I ordered the Connecticut style lobster roll with hot butter and to this day, it’s still the tastiest and freshest lobster roll I’ve ever had.
Attempt to Finish the Lobster Diavolo at Street & Co.
Whenever someone visited Portland, I always saw a foodie post their meals from Street & Co. I would recommend making a reservation to this upscale restaurant located on a cobblestone alley; it’s s always buzzing with people waiting to try their local fish dishes, taste their wine list and dine in the company of their rustic interior. Street & Co. takes pride in sourcing their ingredients from local purveyors, fishermen and organic farmers. Noticing the trend in Portland?
We had some clams, but what stole the show was the Lobster Diavolo for two. Quite honestly, it was more than enough food for probably three or four people. It was filled with lobster, mussels, clams and squid - a seafood lover’s dream.
Have Breakfast at 158 Pickett Street Cafe
On the outside, 158 Pickett Street Cafe looks like an ordinary suburban house; this bakery features a backyard - the perfect setting to enjoy your morning coffee and bagel. My partner, a meat lover, had the Hogzilla, a bagel with egg, bacon, sausage and ham; I had the salmon bagel with dill, capers and red onion. I was speechless after my first bite.
The Holy Donut
If you’re like me and doughnuts are one of your favorite food groups, you must stop by The Holy Donut, hand cut doughnuts made from Maine mashed potatoes. I would suggest coming before noon as they often sell out. We tried the cinnamon sugar one; it was fluffy, not overly sweet and left us craving to try the other flavors.
Go Lighthouse Chasing
It’s no joke when I say that seeing Portland Head Light in person, one of the most photographed lighthouses in America, left me more mesmerized than seeing it on Google Images. But this isn’t the only lighthouse nearby; we made our way to Spring Point Ledge Lighthouse, the only caisson-style lighthouse in the United States that explorers can walk to; and Portland Breakwater Light, also known as ‘Bug Light’ due to its small size, and is another one of Maine’s exquisite lighthouses. This was the perfect way to end a long weekend trip in Portland, Maine.
*I lost most of my photographs from this trip because my phone stopped working after I came back... still hurts my heart.*