Portland, Maine feels like a remote outpost situated at the end of the world, with its far-North reaches contained against an impossibly rocky coast and the deep blue of the Atlantic. One of New England’s most alluring waterfront cities has much to offer from fantastic eateries to an eclectic assortment of boutiques. But perhaps its most quintessential neighborhood is what makes Portland feels familiar, rather than uncharted. Portland’s Old Port neighborhood features cobblestone streets and the working fishing piers that lend the city so much of its character and small town charm. While there are plenty of fetching waterfront neighborhoods up and down New England’s coast, we’re putting together a collection of our favorites from Old Port to convince you it should be your go-to destination for that next road trip. 

The best point of entry is Exchange Street. Known locally as the hub of Old Port, Exchange Street is home to dozens of locally owned businesses, cafes, and restaurants. At the height of the summer, you can expect a throng of tourists meandering the district, but somehow the crowds only add to the excitement. Start at Dobra Tea – the ideal spot for tea enthusiasts and a quick bite. Order a savory pastry and marvel at their pages-long selection of loose leaf teas. Don’t forget to check out Dobra’s selection of Cup of Sea, delicious Maine-based seaweed teas that will let you take home a little bit of the Atlantic. (89 Exchange St.)

Take your tea to go and grab a seat in Tommy’s Park, flanked by a collection of colorful murals and a congregation of food trucks, some of which have been around for decades. It’s a great spot to people watch and take a break. A bit past Tommy’s Park is Gus and Ruby Letterpress. You’re going to want plenty of time to browse their fun  stationery, accessories, apothecary, and home goods. It’s the perfect place to snag quirky gifts and souvenirs. (28 Exchange St.)

Another Exchange Street highlight is Mocean Surf and Skate – this versatile collective features skateboards and surfboards painted by area artists. In addition, Mocean also functions as a gallery space and houses a collection of in-house designed tees and sweatshirts. (10 Exchange St.)

Towards the end of Exchange, you’ll likely catch a glimpse of the lines queueing up for The Holy Donut, a Portland institution. Made famous for its Maine potato donuts using riced Russet potatoes or sweet potatoes and buttermilk from Casco Bay, their treats are known as a healthy alternative to the traditional cake flour donut; perfect for a little indulgence! Their most popular flavor, Dark Chocolate Sea Salt, is exactly what many locals stand in line for. If you’re not yet convinced, their Instagram snaps of ginger-coated sweet potato donuts or vegan potato donuts drenched in blueberry glazes should put them firmly on your radar. (7 Exchange St.) 

When you’re ready for a sit down meal, you’ll happily discover that some of the best eats in Old Port are all within minutes. Your most vexing challenge will be deciding what you’re in the mood for. The Honey Paw serves delicious house-made noodles, kimchi chips, and savory wok-fried noodles at an intimate bar or communal table. A leader in Portland’s burgeoning craft libation scene, Honey Paw has received a lot of attention for their inventive cocktail program as well as  the modern New England spin it puts on its exceptional pan-Asian dishes. Maine ingredients make a welcome appearance in most dishes: Lobster wontons, congee, and Korean fried chicken are local favorites. (78 Middle St.) Ask any Portlander for their “guilty pleasure” restaurant rec, and they’ll undoubtedly mention Duck Fat, a Portland staple and mecca of fried food. The Old Port European cafe has become renowned for its Belgian frites fried in duck fat, its name-sake, and gelato-based milkshakes. Make sure to order the “original Duckfat milkshake” made with traditional créme anglaise. (43 Middle St.) Finally, award-winning Eventide Oyster Co should be your go-to for “the sharpest seafood money can buy.” But this is no checkerboard tablecloth seafood joint, Eventide’s dishes are classics, taken to the next level. Try the infinitely talked-about brown butter lobster roll or stop in for a New England Lobster Bake. (86 Middle St.) 

While the food scene is stellar, Old Port is also home to an eclectic array of Mom and Pop shops. Maine’s coolest comic store, Casablanca Comics, will entertain both fanatics and first-time buyers alike. Their selection ranges from the latest graphic novels to all things vintage, rare, and collectible. (151 Middle St.) Hop on over to Bull Moose Records next, boasting an impressive collection of vinyl, board games, CDs, tapes, and all kinds of gifts. (151 Middle St.) If you’re the type of person who just has to snag a souvenir, Cool as a Moose has exclusive Maine-themed clothing, food, homewares, ornaments. (388 Fore St.) Check out their treasure trove of lobster-themed wares—from calendars to plushies to bumper stickers.

For your sweet tooth, Old Port Candy Co is worth a stop, offering both sugary delights and nostalgia in equal measure. There’s an entire wall in this Old Port fixture dedicated to candies made popular in the sixties! Their fudge is all made in-store and includes some difficult-to-find, unique flavors such as cayenne and wine and sea salt and bacon. Be sure to add some Needhams to your basket, the traditional coconut cream confections dipped in dark chocolate (and made from Maine potatoes, of course!), along with those Maine chocolate covered blueberries that put Old Port Candy Co on the map. (422 Fore St.) If you’ve hit town on a weekend, you’ll want to squeeze in a visit to the Portland Flea-for-All. The market is known for its wide selection of vintage clothing, records, books, and furniture, as well as its diverse antique vendors. Everything you didn’t know you wanted can be found at the Portland Flea-for-All, open Friday through Sunday. (585 Congress St.)

No visit to Old Port is complete without scouring the shelves of Sherman’s Maine Coast Book Shop, Maine’s oldest bookstore and another Exchange Street must, with is well-curated collection of books, stationary, and gifts.Trust their near infallible book recs to restock your bedside table anyday. (49 Exchange St). Last, but certainly not least on our short list, is Kazeem Lawal’s Portland Trading Co on Market, easily one of our favorite stops and the hippest boutique in Portland. His curated general store is one-of-a-kind with an amazing selection of men’s and women’s clothing, accessories, vintage home goods, vinyl, and books. Beyond showcasing Lawal’s infinitely wearable block-printed clothing designs, Portland Trading Co houses the art and handmade wares of some of New England’s most exciting and inventive artists. Be sure to score an original Maine flag cap or tee; they don’t stay in stock for long! (83 Market St.) 

An excursion to Old Port is recommended any time of the year, but festival time is definitely extra. The Old Port vendors are out full steam selling their local wares with tents flanking the event stages featuring a line-up of live music all weekend. The carnivalesque celebration includes a giant puppet head parade gratis the beloved ShoeString Theatre. Take a historic pier and wharf tour or ride the Casco Bay Eye, a giant gondola wheel in the center of the action. Whether you’re sampling the eats or testing out the rock-climbing wall, the Old Port Festival is sure to make your summer hit list. 

Follow us on IG @hipgreenscene to see more!

Carly Roberts is a writer and poet from Virginia, currently attending Emerson College. Her work is concerned with landscapes, space, and travel. She is a contributing writer and intern for Hip Green Scene.

© 2021