Friday
Evening
Dinner and after-dinner dance party

As a recent Maine transplant from Brooklyn, my fascination with the midcoast kicked in early. I had passed through Rockland 15 years ago on a trip to Vinalhaven, but when my friend Brittany and I arrive for the weekend, I quickly realize that this is not the Rockland I knew then. The vibrant city has an eclectic mix of older and younger people—hip even in the dead of winter.

Our journey begins with the most important thing: coffee. We pop in to Rock City Cafe on Main Street, where I order an Americano, and then we head to the back of the building to a bookstore called Hello Hello Books, where I peruse the selection of used, new, rare, and collectible books. Coffee in hand, we explore Black Parrot a few doors down, which offers a high-end mix of tailored apparel, beauty products, and coffee table books.

We check in to 250 Main Hotel, where general manager Ruth Woodbury Starr greets us. Built just two years ago, 250 Main is a boutique hotel designed and crafted by yachtsman and boatbuilder Cabot Lyman, also the owner and founder of Lyman-Morse Boatbuilding in Thomaston. On the corner of Main and Pleasant Streets, 250 Main has yacht-style details and mahogany throughout. In the entry hall of the second floor a curved balcony separating the second and third floors brings to mind the hull of a ship. The lobby is filled with contemporary art, making me feel like I’m gazing into a gallery owner’s dream. We are shown to our rooms, and in mine, a balcony overlooks Rockland Harbor.

I quickly change for our seven-thirty dinner reservation, and we head out down Main Street—we are only a three- to five-minute walk from everything. First we pop in to newly opened Ada’s Kitchen for appetizers, and we order roasted celeriac and fresh mozzarella smeared with pesto. Later, at Suzuki’s Sushi Bar, we choose the chef’s choice for dinner: an omakase platter including ceviche served in a blood-orange peel, local scallops, and fish roe.

After dinner we head down to a dance party at a vintage clothing shop called Daughters. Before I joined Maine Media Collective, I worked in fashion in New York, so I’m always excited to explore the fashion scene in new places. We meet owner Ariel Birke and get to talking about fashion and New York, since she left the city two years ago, just after I did. She is well versed in vintage women’s clothes and specializes in denim—her favorite. I immediately fall in love with her shop. Her boyfriend is spinning records as I’m checking out the threads, and Brittany is dancing. We also meet Emily Seymour, the owner of Curator, another nearby vintage store, who is holding her 11-week-old puppy, Maisie.

Saturday
Morning
A couple cups of coffee and art explorations

I’m up around seven, already ready to rock. I roll out of bed and head downstairs to the lobby for Rock City coffee. I walk out across the street to Rockland Harbor, where it’s windy and cold, and take in the views. Brittany and I take a short walk to Main Street Markets, where I order the Super Green Bowl with coconut, spinach, avocado, almond milk, and chia seeds, all blended and topped with granola. Obviously, I get more coffee, too. Brittany orders the hummus toast with roasted tomato and pepper.

We head out to our first stop, the Farnsworth Art Museum. The museum is still installing an exhibition featuring the work of Chinese artist Ai Weiwei, but we’re able to catch the Louise Nevelson show. Nevelson was one America’s most important twentieth-century sculptors and grew up in Rockland. At the nearby Archipelago, the shop associated with the Island Institute, I buy a couple of postcards showing nautical maps. Next up it’s the Center for Maine Contemporary Art. We cruise through the Boundaries exhibition, a collaboration between poet Richard Blanco and fine art photographer Jacob Hessler, and Materiality: The Matter of Matter, which features large-scale, abstract textiles. Before lunch, we walk out to the Rockland Harbor Breakwater Light. Its breakwater was built in the 1890s from more than 700,000 tons of granite blocks and is nearly a mile long.

Afternoon
Vintage, art, and home goods shopping

At Cafe Miranda, we grab seats at the bar and order salads, admiring the quirky decor and fuchsia walls of the laid-back Rockland staple. Afterward it’s time to meet up with our new friend Emily Seymour at Curator, a hot spot for one-of-a-kind, hand-selected vintage. Emily describes the store’s clientele as men and women who wear men’s clothes, although recently she and co-owner Ben Dorr added a rack of women’s vintage as well. Later, at Daughters again, Brittany and I try on pieces from the selection of women’s vintage ready-to-wear, including Miu Miu and Ann Demeulemeester, and browse Maine-made face oils, soaps, and incenses. Monochromatic visual merchandising inspires me, so I purchase a brown leather woven bag, a wool striped jacket from the ’70s, a vintage thermal, and a deadstock ’70s “perfect” white Hanes tee. I make plans to see both Emily and Ariel this summer. At Dowling Walsh Gallery, we are greeted by an 82- by 100-inch Bo Bartlett work called Christmas, depicting a child on his bike in the snow. We also check out Periscope, a home goods shop offering curated contemporary lighting fixtures, furniture, and accessories.

Evening
Fresh, local food

For dinner, we head out to Sammy’s Deluxe for dinner, a relatively new place from owner Sam Richman, the former chef at Salt Water Farm. Our food is fresh and original, from periwinkles cooked in garlic-seaweed butter and house-made ricotta with delicata and sweet potato to raw oysters and oysters Rockefeller. We take a stroll by the harbor before relaxing in front of the fireplace in the lobby back at 250 Main Hotel.

Sunday
Morning
Adventures in Port Clyde and Thomaston and miniature wooden boats

I’m up at around seven again, and I’m delighted to see snowfall outside my window. From the rooftop of 250 Main Hotel, I take in the view toward Camden Hills as the snow is falling. I snap some shots and head downstairs for fuel. For breakfast, I eat a yogurt bowl with fresh fruit and a croissant along with, of course, coffee. We check out of the hotel and head to the Port Clyde General Store to meet Ron Crusan, director of Linda Bean’s Maine Wyeth Gallery. Although the gallery doesn’t open until Memorial Day weekend, the work is available on its new website. We head upstairs to the gallery, which sells printers’ proofs, rare copies, and posters of Jamie Wyeth’s work. My favorite is called Lighthouse, showing the back of a long-haired boy in a Revolutionary War coat. Crusan tells us that Wyeth used his father’s collection of Revolutionary War props as inspiration for his vibrant, detailed work.

We drive out to Marshall Point Light, which was featured in the film Forrest Gump, for a view toward Monhegan Island, and then we stop at the Maine State Prison Showroom in Thomaston. The shop, open since 1824, offers handcrafted furniture and knickknacks created by inmates. I buy two handmade wooden boats and an embossed leather keychain. After our long weekend, we drive back to Portland, tired and yet already hoping to return in the summer.