Literary City Guide | Portland, Maine

Who says there’s just one safe way to walk, one road properly lit, and the rest - all slippery water, unmarked?
— Betsy Sholl, Coastal Bop

Tour Guide: Emily Connelly

Emily Connelly

Emily grew up in Vermont and college brought her to Maine. Graduate school brought her even further northeast to Newfoundland, but work brought her back; she now studies seabirds in Maine. Emily loves spending time out on the ocean, and also loves spending time with her face in a book. 


Relationship to Portland: I’ve lived here just over 2 years.

Writer you’d like to invite to dinner: Sherman Alexie and Calvin Trillin, though I then might laugh too much to eat anything.

Chef you’d like to prepare the meal: Yotam Ottolenghi

Writing soundtrack: Taj Mahal

Pen or Pencil: Pen

Coffee or Tea? Tea! And the occasional macchiato.

Paperback or Hardback? I aspire to read hardbacks but really am a paperback reader at heart.

Good Reads


Longfellow Books. It’s a local store that has a great selection of new and used books and also is a literary epicenter for the town. The staff are always happy to recommend books and do a wonderful job. It’s my home-base bookstore. 

Sherman’s Books & Stationary. Maine’s oldest bookstore recently opened a fifth location here in Portland and it’s a welcome addition to the Old Port. They have an extensive collection of children’s books and a warm, well-designed interior.

Rabelais. This is an amazing store with an expansive collection of books on food and drink. If you love books and eating you need to stop in for a visit. The store is south of Portland in Biddeford in an old converted mill building. I casually picked up a little book on cooking Chinese food at home and discovered it was published in the early 1900s – there are shelves of beautiful collectable books. If you love books and eating you need to stop in for a visit, as it's the best cookbook store in the country.

Yes Books. Our local used bookstore full of the requisite piles of books you want to pore over for hours. Digging will yield treasures, or at least excellent books you didn’t know you were looking for. 

Carlson & Turner. This antiquarian bookstore in the East End is packed with beautiful vintage books shelved up to the ceiling and also has a traditional hand bookbindery. Everything is carefully categorized and their collections are extensive. 


Portland Public Library. The main branch of our city’s library is located in the center of town across Monument Square from Longfellow Bookstore.

Burbank Branch. Part of the Portland library system and my local library. They have children’s activities here and friendly staff.

Curtis Memorial Library. It’s located up in Brunswick, but it’s a beautiful space to explore.


Longfellow Bookstore. Our local bookstore hosts weekly readings by local and national authors. 

The Telling Room. This local children’s literacy program hosts readings from student’s works, brings national authors to Portland, and also holds Slant, a storytelling series in the spirit of the Moth. 

Maine Writers and Publishers Alliance. The MWPA hosts workshops, readings, and other literary events in Portland and throughout Maine. 

Sherman’s Books. This new-to-our-town bookstore has started hosting readings and other events in Portland – they also have events at their other five locations in Maine.

Word Portland. LFK hosts readings by local and international authors on the first Monday of every month. 


The Telling Room. The Telling Room is a wonderful Portland-based creative-writing and literacy program for children and young adults. They have summer programs, field trips, and after-school programs geared toward helping students become better writers. They publish anthologies of student works, teach students to be good storytellers and interviewers using audio, host student readings, and connect students with authors. 

Wadsworth-Longfellow House. Visit the childhood home of Henry Wadsworth Longfellow and see the beautiful gardens in the summertime.

Space Gallery. This gallery and event space is where you can see cool art instillations, hear great music, and see movies you can’t see anywhere else in Maine. 

Casco Bay Island Ferry. Take the ferry out to Peaks or one of the other islands in Casco Bay for an oceanic view of the city. The islands are great for walks and tidal explorations, though the ferry also runs scenic tours, including an early morning run.

The Maine Brew Bus. There are quite a few local breweries to visit in and around Portland and the brew bus is a fun way to tour them and get all of the details on the best beers in town. 

More & Co. This is a fun store run by a creative team with an eye for beautiful gifts. Their products change quarterly, but they usually have a few well crafted notebooks at hand. 

International Cryptozoology Museum. It’s the only museum in the world dedicated to cryptozoology

Radio Stations. I always like to know where to find NPR or CBC when I’m driving in a new place, so I’ll tell you that our public radio station, run by Maine Public Broadcasting Network, is 90.1 and the local college radio station is at 90.9. 

First Friday. On the first Friday of every month the city’s doors stay open late for everyone to visit galleries and art venues, and the streets fill with artists and craftsmen selling their wares. In the summer you can hop down to the Portland flea-for-all to get some food from the food trucks selling at Flea Bites.

Good Eats


Tandem Coffee Roasters. This is a local coffee roaster supreme based in East Bayside where you can get in-house roasted coffee and espresso drinks along with friendly conversation and a welcoming atmosphere – and maybe a local potato donut if you’re lucky. They’ve just opened a beautiful new bakery and coffee house location in the West End of Portland. Full disclosure: they also sell our family company’s tea

Speckled Ax. Purveyor of wood-roasted beans and more fancy coffee drinks on Congress Street. 

Dobrá Tea House. A fun spot if you love tea and all of the teaware that goes along with it. They have a wide selection of teas from around the world and bubble tea if you’re so inclined.  


Fore Street. A well-known restaurant with well-made, locally sourced food prepared in a central kitchen. The bakery below, Standard, is also an essential stop in the daytime and supplies the bread for Fore Street. Get the mussels!

Eventide. They opened last year and they continue to impress everyone with their oysters, though I think there’s a good argument to be made for their lobster roll prepared in a steamed bun with plenty of browned butter on top. 

Pai Men Miyake. This is a great spot for noodles and sushi along with a great beer selection and tasty tofu buns. They’re open late and worth a drop in, especially in the winter when the boiling broth steams up the windows and keeps everyone warm.

Central Provisions. Recently named one of the best new restaurants in America, this is a great spot for creative cocktails, including bowls of punch for two, and an array of small plates. Even the bread and butter is superb.

Slab. This much anticipated pizzeria just opened and has been very well received. They make some serious Sicilian style pizza with a great dough and sweet tomato sauce. 

El Rayo. My favorite place in town for a taco or two with some tasty cocktails to boot. They use local ingredients including locally made tortillas and have just opened a second location in Scarborough. 

Susan’s Fish and Chips. Not fancy, but if you like fried fish, this is the place! They serve two fried (fresh!) haddock sandwiches for $2.50 on Monday and Tuesday nights, make a mean frappe, and are BYOB.

Food trucks. Portland has a great food truck scene. My favorites are the always delicious Small Axe, the fabulous lobster rolls at Bite Into Maine (bonus, they’re located in Fort Williams at the Portland Head Light this summer), the fantastic tacos at El Corazon, and the vegetarian Indian food at Annapurna’s Thali.

The Bearded Lady’s Jewelbox. Nathaniel Meikeljohn is known in Portland for making creative and tasty cocktails and he’s just opened his own bar on Congress. 


Standard Baking Co. This bakery produces some wonderful breads along with pastries like you wouldn’t believe. 

Holy Donut. The Holy Donut opened just after I moved to Portland, so I feel quite an affinity for the place. It helps that they make some ridiculously good potato donuts made with natural ingredients and Maine potatoes. The chocolate sea salt is the ultimate treat.

Catbird Creamery. My favorite ice cream is in Westbrook but is worth the drive. The flavors are amazing and everything (cones, fudge, toppings) is made in small batches in house. The owner is friendly and generous with the samples. I recommend salted chocolate and strawberry balsamic, though the seasonal flavors are excellent.

Bam Bam Bakery. A completely gluten-free bakery and coffee shop producing some delicious pastries. 

Rosemont Market. I live down the street from one of the branches of this local market – they’re the place to stop in for wine, pastries, sandwiches, fresh local vegetables, or the eggs and milk you forgot when you were at the store. They have three locations in Portland and one in Yarmouth. 

Emily's 5 Favorites

1. Favorite view: The Eastern Promenade has a great view of the ocean – and from the Casco Bay ferry you get a great view of the city.

2. Favorite place to write: At home.

3. Favorite museum: The Portland Art Museum has great exhibits and is a beautiful space. 

4. Favorite coffee shop: Tandem Coffee Roasters. 

5. Favorite thing about Portland: Portland is small enough to feel like home while big enough to produce some amazing restaurants and its own city culture. The ocean is right there and beaches are a short drive away. The rest of Maine is close at hand too – drive west and you find lakes and mountains to explore, head up Downeast to see how beautiful coastal Maine can be, or drive north for hours and climb – or marvel at – Katahdin.