We reached out to our friend Julie of Orchid Grey to take us on a tour of Portland, Maine. With lighthouses galore, plenty of antiques, and the freshest seafood around, we were enchanted by this oceanside town. Without further ado, we’ll let this undercover mermaid show you around.
For many, this is what they think of when conjuring an image of the other Portland – Portland, Maine. And while that picture postcard image isn’t totally off-base (we love our lobster and yes, pretty much everyone here wears Bean boots year-round), this pretty seaside city is so much more than what many folks think of as stereotypical Maine. Located right on the famous Maine coast (we have more miles of coastline than California), Portland offers something for just about everyone – tons of outdoor activities and recreation, incredible food, and great shopping – it’s a unique little city that has everything you need, and nothing you don’t.
Home to artists, musicians, tech workers and fisherman alike (and everyone in between), Portlanders are a hardworking crowd that knows how to have a good time. While the city is vibrant year-round, it really comes alive in the warmer months as residents shake off the long cold winter and people “from away” return to their summer homes on the many islands that dot Casco Bay. While it’s changed over the years, Portland remains one of the most genuine, down-to-earth and unpretentious cities I’ve ever spent time in, all while maintaining a world-class reputation for food, art and music (and seafood, obvi.). As a native Mainer with both parents hailing from Portland, I grew up visiting the city on a near-weekly basis and am thrilled to finally call it home after moving back from Philadelphia just a few months ago. Thinking of taking a trip? I’ve done half the work for you and planned the perfect day from start to finish, below.
Pro tip: Prepare yourself to eat all the things, this city is a food lover’s dream.
Tandem Coffee & Bakery, 742 Congress St, Portland, ME 04102
Start your day at Tandem Coffee & Bakery on Congress St. (there are two locations, this one wins for the cute factor) with a latte and maybe a baked treat or three (you’ll want to grab at least one for the road). Housed in a converted 1960’s gas station, Tandem roasts their own beans and bakes everything on-premise, including Maine blueberry pie, a local delicacy. And they make their own almond milk – so basically this cafe is a dream come true. Don’t expect to get any work done, though, Tandem is WiFi-free so you can truly unplug and enjoy the company you’re with or cozy up with a book.
More coffee shop recommendations, all local roasters:
Speckled Ax, 567 Congress St: Cozy and friendly, with a convenient Congress St. location in Downtown, i.e. close to shopping.
Bard, 185 Middle St: A great spot if you need to get some work done, the staff is super friendly and the big picture window offers A+ people watching. Bard is in the Old Port area, so also convenient to shopping.
Arabica Coffee House, 2 Free St: Great for a quick, unfussy cup of joe if you just need to get on your way.
Standard Baking Co., 75 Commercial St: Not exactly a cafe, but I’d be wracked with guilt if I left Standard Baking off the list. Arrive early to snatch up some freshly-baked croissants, then go eat them at the beach like Chris and I do (conveniently, they serve locally-roasted coffee too).
Portland Flea for All, 585 Congress St, Portland, ME 04101
(Open Friday, Saturday and Sunday only)
After you’ve filled up on coffee and croissants at Tandem, make your way down Congress St. (no need to drive, Portland is super walkable) for some window shopping. From a short stroll down this main thoroughfare you’ll quickly come to understand that Portland is a vintage shopper’s and small-business lover’s dream – and the two passions merge at the Portland Flea For All. Housing a collective of vintage and antique sellers, along with a few makers selling handmade items, the Flea For All offers up serious interior inspo at a variety of price points (as in, you might want to pack an extra suitcase). Here, you can score a vintage tee-shirt and mid-century armchair, an oil painting of a sea captain and a ‘70s wicker peacock chair. The space is beautifully curated so that, even if you walk away empty-handed, you’ll still leave with a few fresh decor ideas.
More shopping recommendations:
Moody Lords Vinyl/Vintage, 566 Congress St: Just across the street from the Flea For All, this record shop/vintage store hybrid is not to be missed, offering something for the vinyl and vintage enthusiast.
Material Objects, 500 Congress St # 1: I’ve been shopping at Material Objects since high school, that is, a really really long time. And I never fail to find something that I can’t live without on a near-weekly basis. Vintage silver concho belt? Check. 1950’s men’s work pants? Check. Silver ’70s earrings? Check and check. They also stock clothing, jewelry and gifts from local and handmade sellers, and a selection of sunglasses to compliment that rad outfit you just bought.
Longfellow Books, 1 Monument Way: It’s rare to find an independent bookseller within city limits these days, so skip the airport magazine stand and give ‘em your business. Longfellow offers new and used books, local publications, small gifts… and happens to be a host home to adoptable cats through the Animal Refuge League of Greater Portland. That’s right… there are cats there. If that doesn’t make your heart melt out of your chest, I’m not sure what will. Go and pet them.
Pinecone + Chickadee, 6 Free St: Offering local and handmade homewares, clothing and gifts, as well as small vintage housewares, Pinecone + Chickadee is the place to go to find that special “Maine souvenir” in the form of a locally-made piece of art or unique handmade item.
Exchange Street / Old Port Area: From Pinecone + Chickadee, Portland’s Old Port is just a hop, skip, and a shuffle away (as in, literally right around the corner). This historic area is home to plenty of small independent shops (be sure to pop in to Blanche + Mimi and Peyote Moon), cafes and restaurants. In the warmer months, music spills out into the streets and the entire area comes alive. You’ll notice the seagulls get significantly louder here, too – that’s because you’re just a few steps away from the wharf (can you smell the fish?).
Portland Headlight & Fort Williams Park, 12 Captain Strout Cir, Cape Elizabeth, ME 04107
No trip to Maine is complete without a trip to at least one lighthouse, and lucky for you, there are at least five within a short drive from Portland’s downtown. Portland Headlight in Fort Williams Park offers the most bang for your buck (don’t worry, it’s free). Grab your rental car or call up a ride share and head over Casco Bay Bridge, through cozy South Portland and on to Cape Elizabeth. As far as lighthouses go, this one has it all: red roof, white paint job, stunning backdrop. In fact, it’s one of the most-photographed lighthouses in America. There’s a small museum inside the keeper’s quarters, and one day a year you can go inside the actual lighthouse (Maine Open lighthouse Day in September). But really, all you need to see is right outside. While there, walk off those croissants by taking a stroll around Fort Williams park, where many of the original structures are still standing.
Two Lights State Park, 7 Tower Drive, Cape Elizabeth: Located just south of Portland Headlight, Two lights does in fact have two lighthouses – along with plenty of trails to explore, rocky shoreline and a pretty legit seafood shack (the Lobster Shack at Two Lights – you might want to save your appetite though)
Bug Light, Madison St. South Portland: Affectionately called Bug Light, Portland Breakwater Light is a diminutive lighthouse shaped like a Greek monument – believed to be the only one of its type in the world. And offers a gorgeous view of Casco Bay and the Portland peninsula. It’s also very cute.
158 Pickett Street Cafe, 158 Benjamin W Pickett St, South Portland, Maine 04106
Once you’ve had your fill of majestic Maine scenery (no, it really never gets old), satisfy your actual hunger at 158 Pickett Street Cafe. This small cafe in South Portland is just down the road from Bug Light and has a cozy, friendly locals-only vibe, offering fresh and quickly made food. The bagel sandwiches are amazing, as are the pizzas offered at lunch. They’re only open ‘till 2pm though, so you may need to hustle, but it’ll be worth it. Pro tip: Get the home fries.
More lunchtime recommendations:
Taco Trio,119 Ocean St, South Portland: if you’re thinking, “tacos… in Maine?” let me tell you, “YES…TACOS IN MAINE”. This place is legit and just may be the best street style tacos I’ve had outside of California and Texas (that trip to Mexico is still on my bucket list).
Pai Men Miyake, 188 State Street -200: Back on the Peninsula, Pai Men Miyake serves up to-die-for ramen and broths, buns and sushi. Also an excellent date spot.
Central Provisions, 414 Fore St: Arguably some of the best food I’ve had in Portland so far, which is saying something because choosing your favorite meal in Portland is like trying to pick between your children. Or cats, as the case may be. Central Provisions serves up small, shareable plates and excellent cocktails – great for dates or just a date with a good book.
Casco Bay Lines Ferry, Variety of routes
With your belly filled, it’s time to see Portland and its outlying islands from a different perspective. Did you know that Maine is home to 4,600 islands? And you can explore eight of them by ferry right in Casco Bay (that big body of water surrounding Portland ;)) While a schooner cruise around the harbor is nice, to me, nothing beats the ferry. It’s easy to pick your poison, either take a boat to one of the islands for some exploring (Peaks is the most popular and populated, Long Island is my favorite) or take the mailboat out for a cruise as it travels to all eight of the stops. I recommend checking the tide charts and ferry schedule ahead of time to plan your trip, and be sure to pack a windbreaker and maybe a layer or two because it gets cold – and keep an eye out for harbor seals and island kids jumping off the landing docks into the bubbles left behind by the ferry, it’s tradition.
Portland Hunt & Alpine Club, 75 Market St, Portland, ME 04101
Once you’re back on dry land, shake off those sea legs with a cocktail and a few small bites at Portland Hunt & Alpine Club. Serving strong cocktails and Scandinavian fare, this pretty cocktail bar is the perfect happy hour stop before dinner or while you wait for a table, the cocktails are strong and I highly recommend the popcorn and bread and butter. Sounds basic, but sometimes basic is best and that’s the case here.
Eventide Oyster Bar, 86 Middle St
If you were suspicious that I hadn’t yet mentioned seafood in a seaside city – in Maine no less – here it is. You could easily spend an entire vacation eating your way through Portland, the food is that good here, so narrowing it down to just a couple recommendations was near impossible. However, Eventide wins based on their lobster roll alone. Not to mention the oysters, clams and cocktails. The food here is fresh (it has to be – it comes out of the ocean that’s just 100 yards away) and the atmosphere is lively, but be warned – there will probably be a wait (but it will be worth it – just go grab a drink at Hunt & Alpine while you wait).
More food/dinner recommendations:
Duckfat, 43 Middle St: Also great for lunch, Duckfat made a name for itself for their gelato shakes… and fries fried in, you guessed it. Duckfat. Indulgent is the word you’re looking for.
Street & Co., 33 Wharf St: If you’re looking for a more upscale, date-night option, Street & Co. will hit the spot. Reservations recommended.
Scales, 68 Commercial St: Another upscale option, Scales is right on the water and offers seafood, wine and a raw bar.
J’s Oyster, 5 Portland Pier: If low-key is more your thing (it’s definitely my thing), hit up J’s for seafood and a beer. Must be ok with/love the smell of fish and low tide, believe me when I say it’s worth it, and we Portlanders grow to love that briney scent!
Terlingua, 52 Washington Ave: Combining house-smoked BBQ and Latin-American offerings, Terlingua serves up food you won’t want to ever stop eating. Have to wait for a table? Wander over to Maine Mead Works or Oxbow Brewing for a sip while you wait.
Julie is a content strategist, copywriter, blogger and freelance writer based in the gorgeous state of Maine. When she’s not doing all those things, you can find her on the beach or up a mountain with her husband, Chris, or curled up at home with her sidekick, Zephyr (a fat and very loved former feral tabby). Her blog, Orchid Grey, covers Julie’s love for vintage and thrifted style, shopping and personal wellness – which she knows is a strange mix… but so is she so it all works out.
Photo credits: Images of Julie by Christopher Sharp, all others – by Julie.