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Three Days in Portland, Maine: Dan Keller

In the next edition in the Three Days in Portland, Maine series, our Operations Coordinator Dan Keller shares his thoughts on all the fun to be had in and around Maine’s largest city.


Ahhh, sweet vacation in Portland! Soak it in, you lucky dog. It’s time for a little well-earned R&R. Before departing on your trip to Maine’s largest city, you might want to have some ideas of great places to go. I’ve compiled a list of cool spots that are true favorites of ours around Greater Portland.

Day 1:

Upon arriving in Portland and getting settled, the first thing I would suggest is to swing downtown to Bard Coffee (185 Middle Street | 207-899-4788) and grab one of the best cups in town. If you’re feeling that you need something a little sweeter, go with the sweet chai for the perfect remedy.

Once you have coffee in hand, set your gaze towards Portland’s East End, and depart on a scenic walk up Congress St to climb Munjoy Hill and along the Eastern Promenade. Even if it is a warm day, you might want to bring a jacket as the ocean breezes can be strong. Fill those lungs with the brisk salty ocean air as you gaze out over the many islands of Casco Bay.

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Munjoy Hill from Portland Observatory. Photo: Jeffrey B. Ferland

This part of town is easily accessible from downtown hotels, as well as from many short term rental properties on the East End of Portland. It is a fantastic slice of coastal beauty nestled on the perimeter of Portland, and it makes it a fantastic and convenient way to get a little exercise while preparing to imbibe in all of the wonderful food and drink.

The Eastern Promenade is a truly spectacular 68-acre public park and recreation area that was designed by the well-known Olmsted Brothers design firm. The walking path at the top covers 1.5 miles, and it rings around the Munjoy Hill neighborhood and occupies the farthest eastern portion of Portland’s peninsula.

The Promenade is home to many historical sites, including Fort Allen Park and the mast of the USS Portland which was a decorated cruiser built in Maine that saw extensive service during World War II. For the history buff, this is an easy visit that is sure to inspire thoughts of grand wooden ships while allowing you to soak in the precious vitamin-D this part of the country needs so badly.

Taking the path from here and heading back down the hill can lead you directly into the heart of the Old Port, perfect for those in search of a refreshing pint (or three).

Go the other way, around the Promenade towards Back Cove, and you’ll find yourself at the beautiful lookout known as Major Charles J. Loring Memorial Park (Corner of Eastern Promenade and North St). Views from this vantage point give you a fantastic scene showcasing the Back Cove and East Deering neighborhoods.

Chase the sun and turn onto North Street to watch the sunset at Sumner Park (North St opposite end of Melbourne St). It’s hard not to turn into a sappy romantic watching this spectacular event, so expect to see the park full of couples during the warmer months.

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Sunset from Sumner Park. Photo: Bd2media

Follow the well-marked Portland Trails path called Fort Sumner Park Steps to bring you back down to Washington Avenue, just in time for cocktail hour and dinner.

An easy left on Washington Avenue will bring you to a neighborhood that is seeing a strong surge in interest and activity in recent years. You will find a number of restaurants representing a wide array of culinary specialties from different corners of the world mingled with tasting rooms and production facilities making some of the finest craft alcoholic products including beer, spirits, and mead.

Among them is a brewery that has a strong connection to the arts, Oxbow Blending and Bottling (49 Washington Ave | 207-350-0025). The farmhouse-meets-warehouse tasting room doubles as an art gallery; check out their Gallery 49 for a range of rotating exhibits that are truly striking. Being a brewery, it’s not uncommon for the exhibits to be beer themed. World class beer in your glass while immersing yourself in the arts; if this doesn’t convert you into an art fan, then I’m afraid there’s no hope. Also, don’t miss out on the dance parties, you might get to see in-house DJs/ brewer extraordinaire Fava Le Chic or Tim Adams throw down.

Now that you’ve successfully baptized yourself in the waters of self-indulgence and cultural excellence, it’s time to fuel up for the next leg of the evening. Head across the street to Terlingua (52 Washington Ave | 207-808-8502) for some amazing dishes anchored by their small-batch BBQ. Like all killer BBQ joints, the smoked board goes fast. I cannot recommend the brisket or the ribs enough (meat sweats commence), although if I wasn’t allergic to shellfish I would be all over the shrimp and avocado ceviche.

The draft list shows plenty of love to local brewers, but with a direct family connection to the Dogfish Head brewery in Delaware, you can expect to see some interesting offerings as well. The inner beer geek in me loves seeing DFH beers on draft lists, brings me back to my early days of exploring craft beer selections and being blown away by some of the outlandish and innovative beers DFH puts out. If you can handle it, get the Tres Leches cake- it’ll blow your mind and provide enough sugar to get you amped for the next leg of the evening’s adventure.

From the stage at the historic State Theater. Photo: The Maine Brew Bus

Now that you are “wined and dined”, it’s time for music and dancing. Portland has multiple music venues that see a range of touring acts, so make sure you check ahead to see who will be in town. I’m a huge fan of bluegrass and jam bands, but the inner metalhead in me still comes out from time to time. I’d recommend heading to one of two places: Port City Music Hall (504 Congress St | 207-956-6000) or State Theater (609 Congress St | (207) 956-6000). Both venues showcase local beers as well, you can often find Allagash, Oxbow, and Rising Tide beer on draft, and many more in cans.

The afterparty, vital to a successful night free of inhibition. Last call here is 1:00 AM – earlier in Maine than other states – so use your time wisely and plan ahead so you can beat the crowd to the next destination and have a drink in hand and apps ordered before the crowd spills in behind you.

Just a short walk away is The Bearded Lady’s Jewel Box (644 Congress St | 207-747-5384) This place is a hidden gem (oh yeah, pun intended). The mirrored glass facade and unsuspecting markings on the door allow only those seeking the Jewel Box to find its hidden treasures. What Nan’l and has team have done to transform cocktails into a new art form is extraordinary. Take a leap of faith and plunge into the unknown, order any of the cocktails off of the menu or request a classic- these folks can do no wrong. If you’re lucky, Nan’l and the gang will be hosting in full-form house homage to Aaliyah complete with laser lights and disco ball.

If you need a late night snack after the show, you can head to Otto Portland (576 Congress St | 207-358-7090). They have multiple locations around the area, but the 576 Congress Street spot is the original and still the best for those late hunger pains. Grab one of their signature slices, specifically the Mashed Potato, Bacon, and Scallion, and you can head back to your lay your weary head down knowing you’ve absolutely crushed your first night in town.

Go you.

Day 2:

Rise and shine sleeping beauty, it’s time to seize the day!

Knowing you had quite the first evening in town and have plenty ahead, clear your foggy head and fuel your belly with a delicious breakfast and coffee at LB Kitchen (249 Congress St | 207-775-BOWL)  My usual order consists of the beet-cured gravlax and caper smear toast known as the New Yorker, and a cappuccino- which just so happens to showcase another excellent local coffee producer known as Tandem Coffee Roasters.

Swing just a few doors down to visit Print: A Bookstore (273 Congress St | 207-536-4778). This is a locally owned bookstore that is also one of my absolute favorite shops in town. You can browse the selections all afternoon or ask staff for recommendations. Seriously, you’re bound to find something that piques your interest. Owner Josh Christie is not only a local Portland historian but also the author of Maine Beer: Brewing in Vacationland (Arcadia Publishing, 2013), a must have for any fan of Maine craft beer. Don’t be surprised to find a few autographed copies on the shelves.

If the weather allows, I recommend venturing off the peninsula to stretch the legs and gain a new perspective of Portland by walking around Mackworth Island (End of Andrews Ave, Falmouth) A beautiful 1-mile loop, Mackworth has a fantastic contrast in terms of the views one will expect to see. On one end of the island, you will be gazing back onto Portland’s Eastern Promenade and parts of Commercial Street. Venture to the other end of the island and you will be looking further into Casco Bay where a cluster of islands spot the interior of the bay like tossed pebbles.

Andrews Ave leading to Mackworth Island. Photo: Flickr/daveynin

If the weather gods are punishing you with the spitting rain and gray skies, then take the opportunity to walk the streets and shop the boutiques of the Old Port. The wide range of shops is sure to provide something of interest for everyone.

For those looking to build a respectable home bar, do yourself a favor and go visit Steve the Bitters Wizard at Vena’s Fizz House (345 Fore St | 207-747-4901). An unrivaled selection of bitters, tonics, mixers, barware, and vintage glassware that will make you want to channel your inner Don Draper and suit up just to spend the rest of your days sipping classic cocktails out of fine glassware and looking oh so classy. If you get the opportunity, ask questions- this is where Vena’s truly shines. The staff is incredibly passionate, knowledgeable, and willing to share.

Once you have worked up an appetite, I highly recommend you seek out one of Portland’s original food trucks El Corazon (often parked on Spring St. 11:30-2pm most weekdays | 207-200-4801) and order yourself a Bad Hombre and a tamale. The housemade salsa really shines here, you can even find jars of it in certain local stores. Sunny days are sure to bring a crowd, so if you’re in a time crunch you can always call in your order. Another option: They also have just opened a full service “restaurante” in the West End (190 State St | 207-536-1354)

Nourished and filled with the spice of life, it’s time to incorporate a little culture and history to round out your afternoon. Head to the western end of the peninsula to visit Portland’s historic West End neighborhood and feast your eyes upon the many brick mansions and brownstones that dot the tree-lined streets. Venture far enough and you will find yourself on the great lawn of the Western Promenade which offers fantastic views of Mount Washington on the horizon on clear days, which is 80 air miles away in the neighboring state of New Hampshire.

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Mount Washington as seen from Portland’s Western Promenade. Photo: Chuck Homler

Once you have worked up a thirst for more of the town’s unrivaled food and drink offerings, swing down to Portland Hunt and Alpine Club (75 Market St | 207-747-4754) for a cocktail. Home to one of Portland’s finest cocktail programs, the staff at Hunt & Alpine have curated a list of original offerings and classics. I’m a fan of the classics, so I tend to lean towards the House Old Fashioned or a Negroni.

Grab a seat along the bar by the front window for some of the town’s best free entertainment; there is not a warm spring/summer night that doesn’t bring out the crowds to fill Tommy’s Park. If you catch it on the right night, you may see some performers from Circus Maine.

One of the questions overheard most in this town is, “where should we go for dinner?” Countless times this has been answered, each time a different way. A simple internet search will produce an overwhelming barrage of recommendations, anyone with a time constraint is sure to be disillusioned by and resort to the first place they see. To avoid all of this trouble and potential misery that will surely follow when you realize everything you missed out on, channel your inner Anthony Bourdain and take a tour of the city using the many restaurants that line the streets of Portland as your waypoints.

When I entertain out-of-state family and friends, we often find ourselves in one of the wooden booths in the corner of Central Provisions (414 Fore St | 207-805-1085). I could go on about the menu and how incredible the cocktails are, but what really solidifies this place in my hierarchy is the whole experience tied together. Incredible food, strong drink, and a dim cozy wood-clad atmosphere where one can indulge in cheerful, food-induced intoxication with friends. Expect a packed house, but this provides the perfect opportunity to throw your name on the waitlist and head to the downstairs bar for a drink and app while you wait.

The Maine beer scene is no joke. Vacationland may soon be replaced with Beercationland if the current trend in the number of brewery openings continue. This isn’t to say we live in a bubble of our own; Novare Res Bier Cafe (4 Canal Plaza | 207-761-2437). ranks among some of the best craft beer bars in the world. The dark brick-laden beer dungeon is complete with a draft list stocked with beer from Maine and abroad so fine it’ll bring a tear to your eye- not to mention a bottle list that will make your buddy’s cellar look like a returnables bag at a frat house. Tap takeovers and theme parties galore, all things craft beer are celebrated in full force. It also happens to be my favorite bar.

If you prefer to end your night with something sweet, Gorgeous Gelato (434 Fore St | 207-699-4309) has something for you. You’ll see people lined outside with cups and tiny fluorescent plastic spoons in hand digging during the warmer months, but make sure you try some affogato style during the colder winter months for a warmer alternative that will add a caffeine buzz to your sugar high. The gelato is all made in-house and is available in pints to go as well.

Day 3:

Once you awake from your slumber, splash some water on your face and head down Congress Street to Speckled Ax Coffee (567 Congress St | 207-660-3333) for your morning cup. I often switch between light and dark roast coffee, really just depends on the particular mood I am in that day. When it comes to the Speckled Ax, the Sock Saunders is the way to go. Chocolate and smoke, with enough heft to clear the mental haze and brighten up those bloodshot eyes. Don’t forget to grab a pound of beans to go as well, you’ll thank me later when it brings back memories of your trip.

Breakfast time. It must be a Keller thing, but all of the men in my family judge a restaurant by one particular dish. It’s different for each of us and totally arbitrary, none of us can claim to be any sort of food critic- we just know what we like. For my brothers Nick and Jeremy, it’s steak and mac and cheese. My dad chose eggs. In his opinion, three-quarters of the breakfast cooks in the world are committing crimes against humanity through culinary atrocities like an overcooked egg. The poor bastards never see it coming.

For me, it’s all about the corned beef hash. I could tell you every breakfast place in town that has a decent hash, but the best, in my opinion, is that found on the menu at Hot Suppa (703 Congress St | 207-871-5005).  The special board always has something awesome that catches my eye, and they offer beer and cocktails as well. My wife Katy is a nurse, and when she would work the night shift, we often found ourselves at the table eating breakfast food and crushing coffee cocktails at 8am. The wait staff knew her by her drink order- coffee and a mimosa. Needless to say, corned beef hash and Irish coffee on a Wednesday morning was kind of a regular thing for a little bit, and it was awesome.

No trip to coastal Maine is complete without visiting a lighthouse. Portland just so happens to be in the vicinity of many, so you have a few options. For a day in the sunshine, Fort Williams Park (1000 Shore Rd, Cape Elizabeth | 207-799-9574) and Portland Head Light (12 Captain Strout Circle, Cape Elizabeth | 207-799-2661) are pretty unbeatable. Portland Head Light sits on a head of land at the entrance of the primary shipping channel into Portland Harbor, which is within Casco Bay in the Gulf of Maine. Commissioned by George Washington and completed in 1791, it is the oldest lighthouse in the state of Maine. The location is 15 minutes off the peninsula in Cape Elizabeth, and the drive out to the park offers a few fantastic views of the ocean and the rocky coastline.

Portland Head Light, Near Portland, Maine. Photo: Ken Lund

The park itself has it all; a playground for those with kids, a historic old fort you can explore, a web of trails throughout the park, huge lawns perfect for frisbee or playing catch, and to top it all off is the lighthouse itself. Summer months bring in musical acts to perform in the pavilion, so check online for scheduling for the rare opportunity to catch an oceanside concert. If you want to stick your feet in the water and walk along the beach, continue along the coast and visitCrescent Beach (66 Two Lights Road, Cape Elizabeth | 207-799-5871) or Higgins Beach.

Before you depart Portland and head back to the old 9-to-5, take the opportunity to sneak in one last dining opportunity to prime yourself for the strenuous journey that lies ahead.

Swing down to East Bayside’s Baharat (91 Anderson St | 207-613-9849) for a late lunch/early dinner. Owners Clay and Jenna are among the many former food truck owners converting or expanding to a brick and mortar facility. The menu is inspired by middle eastern cuisine and incorporates some old favorites from the truck menu. The cocktail list riffs off of the cuisine theme and has a number of classic interpretations and original creations. Like every respectable restaurant in this beautiful town, expect to see four taps flowing with local heros. While there is no bad option when it comes to the menu, there are some things you need to ask yourself first before placing your order; can you honestly look yourself in the mirror for the rest of your life knowing you passed up the chance to order something called the “shawarmageddeon”?

Congratulations, you’ve survived. Now that you are safely back home in your own bed and you have ceased laying siege on your bank account, liver, and waistline, you can start planning your next trip to the sweet shores of Portland, Maine.

When it comes time for another visit, don’t forget to check out The Maine Brew Bus for our new and exciting tour offerings. If you’re lucky, you might even convince enough friends join you on your trip and choose to book a private tour instead. Cheers!

-Dan Keller


Three Days in Portland, Maine is presented by our team members as an honest itinerary of things to do in Portland based on their individual opinions and personal interests. No sponsorship or consideration was provided in exchange for these business recommendations.