Portland, Maine: The First…the Original…the Forest City


Tomorrow the winter solstice will be upon us, and if you are anything like my wife, you are ecstatic for this natural occurrence to begin and then pass. Although the solstice marks the possibility of bleak weather, which can, at times, seem to stretch on forever with no end in sight, it marks something positive and significant for those of you who can’t wait for spring, wishing to hibernate during those months of perpetual wane. Although it is anybody’s guess whether or not the groundhog will see his shadow, scurrying back in his hole, dooming us to six more weeks of hellish frigid winter, the thought of December 22nd is one to enjoy and look forward to, for the prospect of daylight hours extended past their darkest period, is a boon to many who crave vitamin D–such as my beloved wife. But the solstice is not yet fully upon us, and with that, lets celebrate the last place of autumn, Portland, Maine.

Portland has seen itself transformed in the last ten, fifteen, twenty, thirty years. Cities are always evolving, transforming, shifting, like dunes in the desert shaped by the blowing winds, but in the end it doesn’t make the lose of beloved businesses any less painful, for those of us the halcyon days. But today’s Portland is by far different from even this city ten years ago. As neighborhoods undergo gentrification, the downtown becomes artisanal, boutiques abound, and bars and restaurants far out number convenience stores and gas stations. Portland is changing into something different, something that in five years, we again may not recognize. But until that time comes, this small city by the sea holds a special place in my heart, and is my number one location to visit in New England during autumn.


Why Portland at the tail end of autumn? There is something charming about wandering down city sidewalks, your hands shoved in your coat pockets, scarf pulled tightly about your neck, popping into one of the many coffee roasters in the city, to purchase a hot steaming cup of java, staving off the cold biting through our coats. Portland is the perfect place to feel the Christmas spirit as you walk past shop displays, all adorned in wreathes and swags, lights and ornaments, garland and tinsel, snowflakes and fir trees. With the city’s beautiful, lighted decorations, swaying from trees, light posts, and many other spots on the streets, the avenues are alight with cheer, and the night becomes aglow with colors and bright whites.

We are lucky to have a city such as Portland, as small as it is, with so much history surrounding it, and which has been kept as well preserved as it has. Because of efforts within the city, many parks and areas are retained, creating open, green space, in locations which would be rife for development, destroying the seaside charm of this grand city. With that said, find your way outdoors, and meander the paths that wend along the sea. Back Bay Bike Path is always the perfect area to start a gentle walk. This three and a half mile walk is perfect to kill an hour, get a bit of exercise, and just enjoy the city. If you wish to extend this, take the path under the interstate, and take the Eastern Promenade Trail, which will extend this another two miles. This path takes you along Casco Bay with views of Fort Gorges, on Hog’s Island Ledge, and views of Little and Great Diamond Islands, Peaks, and Long Island, with other islands laying hidden, obscured from view. If your views of the islands whet your appetite for adventure, hike on a Casco Bay Ferry out to any of these islands, which you will find at the end of this walk on Commercial Street, right next to Ri Ra’s Irish Restaurant and Bar. If the weather is too brisk, or you just want to hibernate, then find a happy compromise, and brewery hop.


Walking is the perfect mode to get around in Portland, and brewery hopping can be achieved using this antiquated mode of transportation. Although we have found many ways to achieve transportation without actually having our feet touch the ground, sometimes it is best to go back to basics, and put sole to pavement. Grab a pint in the downtown at any breweries and brewpubs within walking distance of each other. Shipyard Brewing Company is the biggest brewery in Maine, and is conveniently located in downtown Portland on Newbury Street. With its frequent tours–no appointment needed–free of charge, a pleasant tasting of beers at the conclusion–must be 21 years or older to enjoy this part of the tour–convenient gift shop on premise, and affable staff, Shipyard is sure to please any beerphile. Down on the water, on Commercial Street, resides Liquid Riot–the brainchild of Novare Res’ owner Eric–a panacea for those seeking great craft beer. With a brewery and distillery on premise, you will get to see the mash tuns and tanks shimmering in the lights of the production floor, behind the plate glass windows above the bar. This brewpub has great food, wonderful staff, classic cocktails, and incredible beer. I have never found a beer I didn’t like from Liquid Riot. They got it right with Novare Res, it makes sense they would make beer as good as they do here.


I cannot gush over all the breweries on here–trust me, I could go on forever–so I will give you a quick rundown. On Fore Street you will find the darkened English Pub called Gritty McDuff’s where malt abounds. I suggest any of their seasonal ales, bitters, and, well, everything. These are good, malty beers. From there you can make your way to Oxbow Brewing tasting room on Washington Avenue for some great saisons. Although not brewed here on premise–they are a farm brewery in Newcastle–you should not skip this great, fresh beer. Right next door, although not beer, is Maine Mead Works, and they have a fresh tasting room with chilled honey wines. On Anderson Street, find Bunker Brewing Company and Rising Tide Brewing Company. Try these out for some great times, great brews, and the company you will keep at each of these locations is always a great time. If you are in for something different but still along these same lines, try Urban Farm Fermentory. Try a flight of their Kombucha, any of their meads, or their ciders. These folks are on the edge of something great and powerful in regards to pushing the envelope in craft brewing and will not disappoint. If you are so inclined to take a taxi cab, find your way to Allagash Brewery and Foundation Brewing, both on Industrial Way, on the outer edge of the city. None of these will disappoint, especially if you appreciate craft brewing.


If breweries and distilleries are not your style, why not try your hand at some culture at any of the different institutions that Portland boasts. Catch a live show at any of the local music venues from the Asylum to Geno’s, The State Theatre to Port City Music Hall or the new Portland House of Music. If you are looking for a splash of art in your life, venture into the Portland Museum of Art. If you are lucky enough to be here on a Friday night from 5p.m. to 9 p.m. admission is free. The sculptures are brilliant and beautiful, and they have some unique and surprising pieces. The Pearl Diver is a mesmerizing piece that I could view and ponder for hours, and the story behind Grant’s statue, and why it is in the museum, is fun one to learn. If you are looking for something not so classical, try Space Gallery, and check out some of their more avant-garde displays and art. This space is not just for static art displays, but media events and entertainment. Check their website first for their hours, shows, and current displays.



Portland has many boutiques and artisanal shops to wander around in search of that quirky Christmas gift, and with the brilliant lights and decorations, it is a perfect place to wander around at dusk and dark, flitting in from shop to shop, enjoying the yuletide sights. The Old Port, once known for rough and rowdy drinking, bar brawls, and street sweepers clearing the streets of bodies after last call, now boasts some of the best spots for boutique shopping, artisanal goods, and unique, interesting wares and sundries. Too many shops, too little time, but to give you an idea, there is a shop that sells various kinds of salt, The Salt Cellar, and a store that peddles only popcorn. Whatever good or product you are looking for, shop local, get your feet on the street, and wander around Portland.



David Jester

About David Jester

David Jester lives in the Midcoast region of Maine. He received a masters degree in American and New England Studies from the University of Maine. David is a full-time firefighter/paramedic and writer, who maintains another blog www.firefighterwithapen.com. He travels the world, but chooses locales that many would never consider for vacation. The world is full of many different and unique places, why not see them all?