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Carbon Cheap Travel 002


A Long Winter Weekend in Portland, Maine

All of the places referenced in this guide are available in a downloadable Google map to take on the road. 

The Place

In the 1980s, Maine’s tourist slogan was Vacationland. Native Mainers responded with their own bumper sticker: Welcome to Maine. Now Please Go Home. The bumper stickers weren’t widespread, but they reflect a decidedly mixed sentiment that’s shared across places that rely on money from seasonal tourism and second homeowners to support year-round locals. The state, previously dominated by blue collar industries like fishing, lobstering, and logging, is undergoing rapid change. Over the past two decades, there has been an influx of money and out-of-staters moving to Maine (reflected in the new tourist slogan: Welcome Home). Portland is perhaps the best, and most stark example of these changes, including gentrification, densification, and a booming tourism industry that has outpriced the service workers it relies on.

Portland is a peninsula surrounded by water on three sides. From Cape Elizabeth, right below Portland, to Rockland on the midcoast, Maine’s coast was carved by glacial retreat into a series of bays, coves, fjords, and granite islands. Portland juts out into Casco Bay, with views of Cushing, Peak, Great Diamond, and Long Islands visible from its shoreline, and all visible from the City’s highest point on Munjoy Hill. In the summer, throngs of tourists walk the City, beginning in the cobblestone waterfront of the Old Port, visiting oyster bars and gentle breezes from the Atlantic while touring the string of lighthouses that dot the granite coast. So, why go to Maine in the winter, when temperatures drop below freezing and seasonal institutions like Red’s Dairy Freeze (bookmark for a summer trip) are closed?

Summer crowds are thinned. Lines are shorter. Prices are lower. Accommodation is easy to find in the center of the City. Most importantly, the slow winter season is challenging for small businesses. Local joints, especially restaurants, appreciate the off-season support.

Maine is also a reader’s haven, and a cozy destination to slow down and get lost in a story. It’s Stephen King’s home state. He was born in Portland, and many of his books are set in rural hamlets and small towns, fictional and real, across the state. This itinerary assumes an interest in books, good food, and a tolerance for frigid winter temperatures. Outdoor walking time is broken up by suggested stops to ward off frostbite and cozy up in cafes, diners, galleries, bookstores, and taprooms.

Portland’s craft beer scene began in the early 2000’s along Industrial Way, where Allagash Brewing opened its doors in an expansive warehouse. Since then, the City has been gentrifying rapidly. Portland’s affordable prices (at least compared to other East Coast cities) drew artists, craftspeople, and chefs to the City. AMTRAK service into Boston made it possible to catch a weekend concert and head back home, even during the chilly winters. Seasonal tourism took off, bringing second homeowners, and the pandemic brought waves of remote workers from Boston and New York into the City, exacerbating the housing shortage and pricing out creatives.

Today, people refer to the City as “Portlyn,” in reference to the rapid gentrification in Brooklyn, New York. Visiting in the winter brings tourist dollars to the City during the hardest part of the year for the service industry.  Some restaurants and shops close for a mid-winter break, often from New Year’s to Valentine’s Day in February, when the deepest cold settles on Portland. Before setting out, check on each restaurant’s website to make sure they are open. If not, no worries - there’s plenty of good eating and drinking in Portland to keep you occupied for a long weekend.

Portland is a city of neighborhoods, each with a different character. Stay in the Old Port, which borders the Arts District, then wander through East Bayside, West Bayside, Munjoy Hill, and the West End.  This itinerary divides the city into three walkable days (with an optional day trip to Cape Elizabeth if the weather is unseasonably warm). Each day includes a series of suggested stops to ward off frostbite and cozy up in cafes and bars.

Setting Out

What to Bring

Pack in layers for the New England winds blowing off Casco Bay into the City. A parka, hat, gloves, and waterproof boots with traction are essential. Just like their outerwear, Mainers are practical. Flannel, jeans, and knit beanies are standard wear. Pack a tote bag or daypack into a rolling carry-on or weekend bag to carry an extra layer - and a book. Maine is the setting for hundreds of fiction and non-fiction books. Settle into the chill with a title or two from the recommendations below, or visit one of Portland’s bookshops and check out their regional suggestions.

What to Read

Any of Stephen King’s books will satisfy horror fans. It is set in the fictional town of Derry, Maine. Under the Dome descends on Chester Mill, a mythical town based on King’s summer retreat in Bridgton, Maine. For an easy-reading mystery, Adam White’s debut novel, The Midcoast, stalks the rise of a Maine family over twenty years, from lobstering in the estuaries along the coast to running opioids from Canada.

There’s an ongoing debate over the great Maine novel, but Olive Kitteridge, the Pulitzer Prize in Fiction winner by Elizabeth Strout, is often mentioned. The series of thirteen stories follows Olive’s life and perseverance in the fictional town of Crosby. The book explores morality, kinship, and the confines of the tightly knit Crosby community. If you’re looking for something lighter, Emily Henry’s Happy Place is an easygoing beach read describing a week-long lobster bake in yet another fictional coastal Maine town. Haven Point by Virginia Hume follows a longer trajectory, tracing a single family’s summer retreat in Maine across seven decades. The novel explores how tradition and family are tightly linked to place in provincial New England. 

For non-fiction readers, E.B. White (the author of Charlotte’s Web among many others) wrote One Man’s Meat, a series of personal essays about his life on a saltwater farm in Brooklin in the early 1940s. White’s essays capture the challenges and joys of rural life, including tips on farming, the changing seasons, and his relationship with his lobsterman, Mr. Demaron. 

The classic children’s book Blueberries for Sal, written by Robert McCloskey, details another adventure along the Maine coast, this one following Sal and her mother as they forage for wild blueberries at the same time as a mama bear and her cub. 

More recently, environmental author Kerri Arseneault penned Mill Town: Reckoning with what Remains, a memoir set in her family’s hometown of Mexico, Maine. Kerri investigates the paper mill that has employed the majority of the town, and also led to massive public health problems that have been ignored by government officials for decades. Kerri opens questions about the legacy of not only Mexico, but thousands of other communities that depend on industrial mills and plants that may be poisoning them. 

If you’re reading on your phone, journalist Colin Woodward’s twenty-nine part series Unsettled is downloadable from the Portland Press Herald as a PDF. The serial begins 13,000 years ago and follows the Passamaquoddy people into the present day. Like Mill Town, the project exposes a side of Maine that is often ignored: looking at uninvestigated killings and state conspiracies that continue to harm the Passamaquoddy.

To the north toward the Canadian border, Downeast: Five Maine Girls and the Unseen Story of Rural America by Gigi Georges follows the story of five women in Washington County as they study through high school. Georges treats each person with empathy as she examines the challenges and opportunities that stem from growing up in a tight knit community with an intergenerational class structure and limited economic opportunities. 

How to Get There

The AMTRAK Downeaster leaves from North Station in Boston, accessible by T on the Green and Orange lines. There are five daily round trip journeys, with each leg running around two and a half hours. Take the Northbound train from Boston at 5:20 PM on Friday to begin your journey. 

Coming from New York City? Pack an extra book and take the four hour Northeast Region from Moynihan Hall at Penn Station into Boston and transfer at South Station onto the Downeaster. From Boston or New York, you’ll arrive at the Portland Transportation Center on the outskirts of the City. 

From the Portland Transportation Center, take the Metro BREEZ Northbound from the Transportation Center to Monument Square ($4 each way), where you can switch to any of the Greater Portland Metro’s buses that run across town.

Where to Stay

There are options for accommodation at every price point in Portland. To be centrally located, try to stay around the Old Port, a neighborhood in central Portland, that’s an easy setting out point each day. For solo travelers and budget seekers, the Black Elephant Hostel is the only hostel in Portland. Located just across Franklin Street in East Bayside, the hostel is steps away from the Old Port. Nearby, The Inn at Park Spring is a bed and breakfast in an old brick building with private bathrooms, located in the center of the City. Further inland on the peninsula, the West End Inn is three blocks away from the #1 bus that runs along Congress Street into the Old Port.

How to Get Around

Once you’ve arrived in Portland, you can easily take the bus around the City. The Greater Portland Metro serves the City. Metro Route 1 runs along Congress Street, stopping at Monument Square, and traveling to the tip of the peninsula in Munjoy Hill. Monument Square is between the Old Port and East Bayside neighborhoods, making it a convenient central location to walk from if you’re staying outside of downtown Portland. Any journey on the Metro that’s less than 90 minutes runs just $2.

What to Do and Where to Eat: an Itinerary

A winter Portland trip is best broken down into different neighborhoods to explore throughout the day. This three-day itinerary is split into three areas: Old Port, Munjoy Hill and East Bayside, and the West Side. The order is up to you. There’s enough to eat and drink through Old Port and the East End for a week, though you might consider strolling the wide boulevards of the West Side on your last day.

Maine’s craft beer scene began on Industrial Way, beyond the peninsula of Portland. The list of breweries included here is limited to taprooms within walking distance of the Old Port, but plenty of restaurants and bars have offerings from Industrial Way breweries like Allagash and Shipyard Brewing on draft. Non-alcoholic options are available at each brewery. Cannabis is legal in Maine. Jar Co. is located centrally downtown, while SeaWeed Co. is just north of the Old Port. 

Friday: Old Port and Downtown

The Old Port is a walkable home base to explore the city. The brick and granite laid streets are quaint and easy to navigate. After you arrive on Friday evening, check into your hotel and walk down to Wharf Street, the anchor of the Old Port. Once you’re near the water, stop into Central Provisions. Reservations open two weeks in advance for this Old Port staple, but walk-ins are welcome and usually land at the bar. After dinner, head to Arcadia for a nightcap to play skee-ball, pinball, and Pacman on their old-school arcade machines, open until 1 AM. 

Start your morning at the Speckled Ax for a cup of coffee and a pastry, or head to Holy Donut before noon for a Maine potato donut back on Wharf Street. If you forgot a book, Sherman’s Maine Coast Book Store has been in business since 1886. They specialize in books by Maine authors and books about the state if you’re looking to take home a souvenir. Nearby, Longfellow Books is a shelter for cats looking for a new home, and they also have a roster of author events that are posted on their website.

Find sunshine on a late morning walk to the Portland Museum of Art. The permanent collection includes works by marine landscape painter Winslow Homer and Modernist Marsden Hartley, housed across several buildings, including the Charles Shipman Payson Building designed by I.M. Pei and Partners. Throughout the month of February the museum screens films from their collection on Saturday afternoons.

Spend the late afternoon in Maps, a hole-in-the-wall bar covered floor to ceiling in vintage maps. Nondescript from the outside, wander in and enjoy an Allagash on draft while reading or listening to the record player. If you’ve warmed up, consider a visit to Mount Desert Island Ice Cream, an outpost of the Acadia staple, is open through December, and reopens in early March. They churn homemade, seasonal flavors like corn, blueberry jam, and squeezed lemon sorbet.

No trip to Portland would be complete without a visit to The Highroller Lobster Co. Highroller started as a pushcart that two friends wheeled around to breweries in Portland before they opened their downtown location. Sit inside at the bar and chat with the bartender over a beer, fries, and Lobster Roll with lime and jalapeno sauce. Finish your night by walking over to Novare Res Bier Cafe for thirty-three beers on tap, most from surrounding breweries. End the evening early to be first in line for Miss Portland Diner on Sunday morning.

Sunday: Munjoy Hill and East Bayside

Miss Portland Diner is built into a Worcester Lunch Car Company dining car that sits permanently on Marginal Way behind Back Cove Park. Technically located in West Bayside, squeezed between the Old Port and East Bayside Neighborhoods, it’s worth it to make the trek north to sit at the marble countertops drinking bottomless coffee with their french toast breakfast sandwich dipped in Maine 
maple syrup.

Follow the coast to Cove Street Arts, Portland’s largest artist space. If you need to break up the trek, grab a warm beverage from Coffee by Design. Just like in literature, Maine packs an outsized punch in the American art scene. The galleries, exhibition spaces, and studios focus on contemporary Maine artists and works. Keep walking toward Goodfire Brewing Company and Lone Pine, two tasting rooms that are located a minute away from each other. Try a half pour at both and then walk down the hill toward Oxbow Blending and Bottling, which hosts swaps, trivia, and live music most afternoons. Before dinner, stop in at the Portland Observatory to tour the marine signal station. The building was erected to give merchants a competitive edge - the telescope at the top of the station, which looks like a brick inland lighthouse, could spot ships coming into port from 30 miles out to sea.

For dinner, warm up with noodles at the massive communal table at The Honey Paw. The bistro is owned by the team behind Eventide Oyster Co., the seafood institution that has opened outposts across the northeast since opening in Portland’s Old Port in 2012. Start with the kimchi mussels and dive into the lobster tom yum soup or mapo doufu over rice. If you’re feeling something more casual, walk another block to Duckfat for Belgian frites twice-fried in duck fat. If that’s not hearty enough for you, top the fries off with a duck fat poutine. Budget time to digest in the cozy booths with your book. After dinner, walk one street over for a drink with the locals at Tomaso’s Canteen. This cinder block dive specializes in canned beers and late-night hot sausage sandwiches. 

Monday: West End 

Spend your last day in Portland walking the streets before you sit for hours on the train. The West End is the sleepiest and most residential of the three neighborhoods, with more limited dining options. Don’t skip a day walking the wide boulevards with brick homes down to the Western Promenade. Start the day at Becky’s Diner, a waterfront institution serving endless coffee and greasy spoon fare. Walk the industrial waterfront to the Port Authority and turn back into the city at Harbor View Memorial Park toward the Western Promenade. This elevated park offers views across New England into the White Mountains on a bluebird day, and is somewhat sheltered from the winds blowing off Casco Bay. Pick up some coffee beans from Tandem Coffee and Bakery to brew back at home. 

When your extremities are frozen, you have two options: Hot Suppa or Ugly Duckling Maine. Hot Suppa serves Southern meals made with New England ingredients, like shrimp and grits, barbecue pulled pork eggs benedict, and a local mushroom scramble. The restaurant, run by two brothers who focus on serving affordable meals for the neighborhood, is only open until 2 PM. If you need more time to digest breakfast, walk toward the Ugly Duckling Maine, a luncheonette serving breakfast sandwiches and pancakes that drags into the early afternoon with cocktails, beer, and wine. Close by, Ruski’s is a neighborhood dive with darts, wings, and regulars you won’t find at Portland’s craft breweries. If you can squeeze in dinner, walk up toward Pai Men Miyake for twelve varieties of ramen, as well as donburi, bao buns, and a large selection of sake. If you’re crunched for time and dinner’s off the menu, walk back toward the Old Port to collect your luggage from your accommodation and catch the BREEZ bus back to the Portland Transportation Center and onward home. 

Cape Elizabeth: If it’s Warm

Before setting out, check the forecast. If the weather is warm and you bring warm layers, spend a day walking out to the iconic Portland Head Light in Cape Elizabeth. Located south of Portland, Cape Elizabeth is a suburb of rolling coastal estates that’s accessible on the South Portland Bus (Route #21), which stops at the intersection of Congress Street and Center Street in downtown Portland. Take the bus to the Pillsbury and Cottage Street stop and walk one and a half miles down Cottage Road (which turns into Shore Road) to the lighthouse and museum. The views out across Casco Bay are incredible, and the museum includes several rooms describing the evolution of light keeping on the Maine coast. If it’s too chilly, plan a return trip for Maine Open Lighthouse Day in early September (prepare for an early morning, timed entries into the building sell out by 6:30 AM). On your way there or back, stop at the Cookie Jar for a home-baked pastry and hot coffee to warm up.