Full Pockets

O pening a takeout box from Madeline’s Empanaderia was like unwrapping a birthday present. The empanadas and tostones inside were bundled in festive black and white paper, their heady aroma boosting the feeling of anticipation.

It was a rave recommendation from a friend that had led me to pandemic baby Madeline’s. Co-owners Maurice Watson and Hazel Lebron each owned food trucks—Lunchbox 23 and Caribe Soul, respectively—before the shutdown. They decided to join forces on a brick-and-mortar space, and “fortunately or unfortunately, lots of restaurants were closing, so we had many spaces to pick from,” Watson says. They chose a homey location with board and batten siding at 48 Middletown Avenue, “between but close to many different neighborhoods.” So far, he says, the cozy restaurant with a small outdoor seating area is “getting lots of love from the industrial businesses nearby.”

sponsored by

The Community Foundation for Greater New Haven

Watson conceives and cooks the food, while Lebron “works the front end” and curates the wine, beer and “vibe of the place.” Each month she works with a different visual artist who displays their work on the walls. Named after Lebron’s daughter, Madeline’s Empanaderia is “largely Caribbean-based,” Watson says, “and reflects [Lebron’s] love of food and Puerto Rico.” The space is used for occasional popup shops or community events like last Sunday’s open mic in honor of Black history month.

With a menu boasting over 20 empanadas (most $3 each) as well as a range of small plates and sides ($5-13), my daughter and I first sampled the tostones, green plantains that have been lightly fried, smashed, then fried again until crisp. These were served sprinkled with salt and accompanied by a trio of bright, delicious sauces—salsa verde, pico de gallo and chipotle mayo—adding zing and depth.

Then it was on to the empanadas. Counterintuitively, we started with the sweetest of our choices, the Guava Lava: mozzarella and guava paste in a crispy, flaky shell lightly sprinkled with powered sugar. “Wow! That’s unexpected. And delicious,” said my daughter as she took another large bite.

Next up was the Ropa Vieja filled with tender braised beef and Cuban rice, followed by the Funguy (succulent herbed mushrooms), the Bacalao (lightly briny cod) and the Roast Green (spicy Brussels sprouts and sweet potato). We kept spouting adjectives like yummy, fresh, even scrumptious. My daughter commented that the empanadas were “terrific hand food,” firm enough to hold without springing a leak.

The menu is rounded out by a thoughtful selection of small plates including ginger beer wings, chipotle costillas (ribs) and picadilla croquettas (potato balls with savory beef and cheese filling) as well as plantain, rice and potato sides. Happy hour happens from 4 to 7 p.m. Tuesday through Saturday, and brunch is served Sundays between 11 and 2.

If you want to try the same empanadas I did, head over sooner rather than later. Watson likes to switch up the offerings every few months and is currently working on a menu for spring. By then, the weather should be warmer, and Madeline’s could be cooking up something new.

Madeline’s Empanaderia
48 Middletown Ave, New Haven (map)
Tues-Wed 11am-7pm, Thurs-Sat 11am-9pm, Sun 11am-2pm
(475) 238-6026

Written and photographed by Heather Jessen. Image 2 features Maurice Watson.

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Heather Jessen is a poet and writer who likes asking questions. She’s in awe of the educators, artists and social workers who’ve helped New Haven kids and families during the pandemic.

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