Maine Madness – 48 Hours in Portland


“I would really rather feel bad in Maine than feel good anywhere else.” — E.B. White

Lighthouses, Lobster Rolls & Golden Retrievers. These are a few of our favorite things and good old’ Portland, Maine is the promised lane for ’em. This time of year, NYC’s muggy heat & packed streets bring a chaos that drives even the squirrels away. Truth be told, we wanted no part in our city’s 4th of July festivities.

So, we reserved standby tickets (see below***) on Jet Blue’s early AM flight to Portland. Flying out on the 4th of July? Not our wisest move. Come morning, every seat on the flight was taken & we scrambled fast to find an alternative. And here’s the start to our Maine curse.  We settled for a direct flight to Boston and a 2 hour bus-ride to Portland. Not ideal, but hey – we signed up for an adventure & the pine tree state delivered.

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Fort Williams Park, Portland, Maine

Day 1:

Rental bikes: our first order of action the second we arrived to Portland! We’ll usually rent a car via Turo but it was out of the question for this trip. Portland is small and everything is relatively close. Plus, its bike trails are just begging to be explored!

We grabbed a few bikes downtown at The Encyclepedia (hehe) for a sweet half day rate of $20. Then, we headed straight for Portland Head Light – Portland’s most iconic sight. The route is a manageable 5 miles (around 30 min cycling) through wide bike lanes and trails. The heavy heat, a few wrong turns, & an impromptu squirrel rescue attempt slowed us down some more.

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Bike Route to Portland Head Light

We worked up some sweat but it was well worth the view. Portland Head Light ain’t one of the U.S.A’s most iconic lighthouses for nothin.’ She stands tall on Fort Williams Park, watching over blue seas and passing sailboats. We sure aren’t the first to fall in love with her.

“Portland Head and its light seem to symbolize the state of Maine—rocky coast, breaking waves, sparkling water and clear, pure salt air.” – Edward Rowe Snow

Portland Head Light, Cape Elizabeth, Maine

Some fun facts: she was built in 1784 (wowza!!!). She’s the oldest lighthouse in Maine AND, she’s also the most photographed lighthouse in America!

Apparently, it’s possible to tour the Keeper’s Quarters (little house next to the lighthouse) BUT it’s well worth it to lie on the grass and just admire her from afar. There’s also a small beach at Fort Williams Park that’s made for daring souls. Swim at your own risk: Maine waters are rocky & chilly. Not to mention – they’re home to lobsters.

Fort Williams Park, Maine

All that sightseeing worked up one heck of an appetite.

Our next stop? Arguably 90% of the reason we made it up to Maine. If you’re after a classic, Americana summer – Red’s Dairy Freeze is a roadside jackpot. This 1950’s soft swerve shop hits you right in the feels, proving that life’s all about the little things.

“Red’s Dairy Freeze is here to save the hot, humid day. Family-owned and operated since 1952, Red’s is a South Portland staple, offering some of the tastiest soft serve ice cream around. ” – Eater Maine

And yes – we’ll have red, white & blue sprinkles with that.


Red’s Dairy Freeze, South Portland, ME

One small lesson learned in Maine: Sometimes, life throws ya a curve ball & your bike flips over as you’re speeding downhill. If it happens, remain calm & remember: soft serve ice cream cures just about anything. (But seriously – go see a doctor).

vanilla soft serve – doctor’s orders

But did you really go to Maine if you didn’t have lobster? Flyin’, bike-ridin’ & ice cream devourin’ really wipes you out. We needed a quick fix for a long day & the Portland Lobster Co was our pick. There’s a ton of options downtown but if you’re lookin’ for a budget dinner by the water – this is your place. We shared a lobster rollfried lobster with aioli & a crab-cake burger – all were delicious.

Portland Lobster Company, Maine

Day 2:

Aboard the Wendameen Schooner

A good night’s sleep, a hearty diner breakfast & potato donuts (seriously) marked the start to our last morning in Maine. With just a few hours to spare before flying out, we were eager to breathe in Maine’s salty breeze one last time. Will we ever pass up an opportunity to sail?

Wendameen Schooner, Portland, ME

Ask anyone in Portland & they’ll say the Wendameen Schooner is one of the most beautiful & historic sailboats in the world. They aren’t wrong. She’s over 100 years old & traveled all over the Americas in a past life. Today, she’s docked in downtown Portland & journeys calmly along the coast of Maine.

She was built in East Boothbay, Maine, and was launched in 1912, when she took center stage in the golden era of fast, sleek ocean schooners.” – Tall Ships Portland

We booked a 2-hour ride through Tall Ships Portland for $45 each. Pricey but worth every cent. In a famous coastal city like Portland, it’s a sin not to climb aboard one of its many wooden wonders.

Aye, Aye, Captain!

All in all, Maine wowed us once more with its small town charm and New England allure. It’s easy to get caught up in NYC’s go-go-go mentality. It’s places like Portland that make you sit back, relax, and enjoy the ride.

Until next time, Maine. Catch our next trip to Chicago, Illinois. Coming real soon!

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