The cultural capital of Maine has outstanding offerings for lesbians.
A little over an hour by air from New York City is Portland, Maine, a charming and picturesque port city with a concentrated population of over 60,000 residents. Flying in you might be dazzled—if it’s summer—by the sapphire blue water and emerald green vegetation.
Once you land and make your way to the historic center you will marvel at the lovely examples of architecture that survived four terrible fires and a couple of terrible battles, which earned the city its seal of a phoenix rising from the ashes, and its motto “Resurgam” or “Rise again.”
Indeed, Portland is a survivor and has reinvented itself numerous times. Located on a peninsula in Casco Bay on the Gulf of Maine and the Atlantic Ocean, it was originally inhabited by Indians, and then settled by white men as a site of trading and fishing.
It grew into a bustling port and commercial center, reached by both rail and by sea, once icebreakers were invented for Canadian exports. Today, the prettiest—and certainly the most touristy—part of town is arguably the Old Port, which is still a commercial center, selling everything from nautical mementos to souvenirs to fresh local fish; and the vibrant and pleasant Arts District, which follows Congress Street through the city center.
Only a couple of laneways and cobblestone streets down near the piers speak of the city’s rough-and-tumble past, and even they do so delightfully. Finance, petroleum, and tourism form the backbone of the city’s economy now, and the tourism is especially welcoming of LGBT travelers and hipsters.
I visited for Pride, on June 10-19, and was thoroughly charmed by the city and its people, as well as this great event, which had plenty on for lesbians, including spoken word poet Andrea Gibson and DJ Mary Mac. I mingled with the local lesbians, two of whom have transplanted themselves here because they were charmed by the place too!
Kim Chesterfield, who works with the local Pride organization, came to Maine in 1992 to work at a summer camp. “I fell in love with my first partner and with Portland… I just never left,” she says.
What keeps her here is no doubt her long-term partner, Kate Pinkerton, who hails from Burbank, California and also prefers Maine—but also the mix of small town ease yet sophistication normally found in much larger cities. “We have access to the most amazing art, music and food! It’s clean and safe.
It has easy access to the mountains and rivers and it’s on the ocean. The people here are just so open and welcoming,” she says. Together they enjoy biking, camping, kayaking, bird watching, and often end outdoor fun with a visit to a local brewery or a great restaurant—and there are many to choose from. Then there’s the live music scene, which is how they first met.
As Fundraising Lead Chair for Portland Pride, Chesterfield was particularly pleased with her town’s rallying cry in support of Orlando. “This is the third year of Pride Portland putting on the Pride events in Southern Maine. While we do events year round, our focus is on 10 days of Pride,” says Chesterfield.
“This year was huge. I think the biggest factors were: The weather cooperated, we added some different events and, of course, the tragedy in Orlando. Everyone wanted to be with their community. Allies wanted to show their support.”
Chesterfield kicked off the event on the Friday before the shootings. “When we woke up Sunday morning to the news we were so saddened, and scared and shocked. We ensured that everyone felt safe at our events.
And we needed to grieve. It was actually so healing to be emerged in the community throughout the week. From the first vigil to the closing Tea Dance… Every day made you feel more supported, more loved and more proud.”
After hearing the Orlando news, Chesterfield’s partner Kate wanted to ride up front of the Dyke March and the Parade with the Dykes on Bikes. Even though she realized that she could be a target, she was not afraid.
“She would be out front as she always is, with her peers, proud, acting as protector, guardian and symbol of power that the Dykes on Bikes represent,” says Chesterfield. “It was awesome to watch that process and see the strength come forward. That security and confidence helped others feel safer and more secure about participating.”
The Portland lesbian community is tight knit but open, too, and the scene welcoming. “It’s a really mixed crowd,” says Chesterfield. “Very inclusive for the most part. There isn’t a lesbian specific bar in town. There are four LGBT bars but they are often frequented by our straight community. Really, anyone can go anywhere here. It’s really nice to be able to feel comfortable going wherever. That just how Portland is.”
Where to stay
The Westin Portland Harborview is located on High Street in the heart of the Arts District in downtown Portland. Step outside and discover the Portland Museum of Art and a number of wonderful galleries, boutiques, antiques stores, jewelers, vintage stores selling cool clothes and vinyl, and more. It’s also a short walk to Portland’s Old Port district and Casco Bay, and along the way are some very good and quite affordable restaurants, too.
Formerly the Eastland Hotel, the Westin Portland Harborview reopened in December, 2013 following a $50 million renovation as the first Westin hotel in the state of Maine. With 289 contemporary-style guestrooms that have “heavenly” beds, free Wi-Fi, and lots of natural light and pleasant views, it only gets better at the Top of the East Lounge, which has stunning vistas of Portland, plus serves cool cocktails, good wine, and small plates such as fresh chilled shrimp and lobster sliders.
This is where you want to be at sunset to watch the light change and enjoy a bird’s eye vantage point of the city’s offerings.
Congress Squared (or C²) is the hotel’s restaurant, staffed by a young and attentive group of servers. This is where to have breakfast, lunch and dinner daily and take advantage of happy hours, specials, and dishes showcasing regional ingredients. In summer request a table outside on the patio on Congress Square and watch the world go by.
Where to eat
It’s worth venturing out to try the excellent local seafood, and nowhere serves it fresher than two of my favorite places: Eventide Oyster Co, which is where you should go for local varieties of freshly shucked oysters; and the iconic Portland Lobster Company on Commercial Street in the Old Port.
Both of these establishments receive more than one shipment of produce a day—that’s how fresh it is. If you’re not a seafood lover and want something casual, I can vouch for the pizza slices and pies at OTTO on Congress Street.
If you’d like to eat gay, here are the recommended LGBT-owned restaurants: Katahdin; Caiola’s; and Wild Burrito at 581 Congress Ave.—with the latter a prominent sponsor of the Pride Parade.
Things to do
Portland is situated spectacularly on the water so it’s highly recommended that you take a Casco Lines Ferry to Peaks Island, a pretty little community with lovely homes, coves, and pebbly beaches. It feels a million miles from care, but it’s only a short trip and a few bucks to get there. Want more ideas? See Kim and Kate’s recommendations below.
Kim & Kate’s Top 6 Portland Picks for Lesbians
1. Go for a bike ride. The trails and bike paths are part of the East Coast Greenway from ME to FL. The views are incredible! Lighthouses, bird watching, beaches and more!
2. Visit Ryan Smith behind the bar at Eventide Oyster Bar for oysters and a Dirty Dirty Martini made with olive brine, oyster brine and hot sauce. (Oh, and the browned butter lobster roll is to die for!)
3. Get in line early for bagels and pimento cheese at Scratch Baking Co. in South Portland then pop down to Willard Beach for a walk with your pup.
4. Hit up LK and Laura of Bowline Co. for a private shopping of their amazing bow ties and grab a few. They are handmade and always a limited edition!
5. The Portland beer scene is amazing! We prefer to walk to most of them but you could hop on the Brew Bus and make the rounds in style.
6. Bonus… Need more flannel?! Head north about 20 minutes and grab some at LL Bean.